#572 - Kenny Chesney on Fame, Music and Can He Ever Go Unnoticed in Public?

Country music legend Kenny Chesney joins the show to talk about the aspects of his career fans don’t always see or hear. He shares the hit song he’s gotten tired of playing live, breaks down how he physically preps for stadium tours, and looks back on the early failures that shaped his career path before things finally clicked.

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Episode Transcript

Speaker 1 (00:06):
Kenny, thank you for being here, Thanks for having me man,
good to see you. This is our first Netflix episode,
so I am honored. Thank you very much. I have
my hometown sign up here. Yeah, I see that seven
hundred and seventy two people story behind it? Yeah, or
not that one? Well, no, that's the literal. Well, they
had three of them, and I asked for the design

(00:28):
of it, and they sent this. The designs ordered it.
But the one in my hometown literally has bullet holes
all in it.

Speaker 2 (00:33):
So somebody didn't like Bobby.

Speaker 1 (00:34):
Somebody. I think he's a tired of my name. Somebody
on the town.

Speaker 2 (00:38):
Somebody was jealous of Bobby.

Speaker 1 (00:39):
How many people in Lectoral, Tennessee.

Speaker 2 (00:42):
Oh, I don't know, maybe a little more than seven hundred.

Speaker 1 (00:46):
Did you guys have like a Walmart or anything?

Speaker 3 (00:48):
No?

Speaker 1 (00:48):
Yeah, I mean obviously we had.

Speaker 3 (00:50):
A church, We had a post office, we had a
couple of meeting threes. And that's I mean, that's like
an old school grocery store. Like not. It was a
mom in pop grocery store. It wasn't like any of
the change. You know, we had to go in the
Knoxville to get to go to Kroger or anything.

Speaker 1 (01:08):
Like that. I was gonna ask if there was town,
because for us to go to town, then we went to
Hot Springs and that's where Walmart was.

Speaker 2 (01:15):
That's right.

Speaker 3 (01:16):
No, we would go into town at Christmas. I mean,
I didn't go down a lot of roads as a kid.
I went down the road I lived with my grandmother
for three or four years, so that meant I knew
the road to church on Wednesday night, on Sunday morning
and Sunday night, and I knew the.

Speaker 2 (01:34):
Road to the ballpark where I played ball.

Speaker 1 (01:36):
That's it.

Speaker 3 (01:37):
But my grandfather was one of these people, you know,
during Christmas, he goes, let's all get in the car
and drive to Knoxville to see the lights.

Speaker 2 (01:45):
And that was a big deal.

Speaker 3 (01:46):
So how far was that forty five minutes maybe, but
it might as well have been four or five hours.

Speaker 2 (01:53):
We didn't go that much. So that's how I grew up.

Speaker 3 (01:57):
So that when I came in and saw that, oh wow,
because they put one up for me in my hometown
and somebody just took it down.

Speaker 2 (02:03):
They just did. They didn't want to see it. So literally, there.

Speaker 1 (02:06):
Wasn't a compliment like someone stolen because so.

Speaker 3 (02:10):
Maybe it's I mean there's a small chance that that's it,
but you could just I don't know, you could just
feel the jealousy or something that you made it. Either way,
it was gone and they didn't put another one back,
but they did put another one, like right down from
where my grandmother used to live, and this one did
make me happy. They put another one up because right

(02:31):
in front of the Latoral City Hall there was this
big sign from me growing up that said home of
Country Music Entertainer where they say Chad Atkins right. Well,
now there's one of me right beside ched Atkins, and
that makes me very happy because that was a kid. Look,
I was a kid looking at that. Now I got

(02:52):
my own sign right next to him.

Speaker 1 (02:53):
So you mentioned your grandma and grandpa. My grandma adopted
me and raised me growing up. What was the story
with your grandparents raising or at least living with them.

Speaker 3 (03:01):
Well, my mom, my mom, and my real father divorced
before I was one, and then my mom got married
to my grand I mean to my stepfather, and then.

Speaker 2 (03:11):
He went to Vietnam.

Speaker 3 (03:12):
So we lived with my mom's parents for three or
four years. So that's where I first heard country music.
You know, I I uh would get up every morning
when uh, this is going a little further back. My
mom and my grandmother were pregnant at the same time
having me and my aunt Missy no way, so they

(03:37):
were in the hospital at the same time almost having us.
So I grew up with my aunt like I thought,
you know, I thought she was my sister, but not really,
she was my mom's sister. Makes sense why this is
really for people listening on Netflix.

Speaker 2 (03:51):
It's from really East Tennessee stuff. But that's how it happened,
you know.

Speaker 3 (03:57):
So when my Aunt Missy and I got old enough
to go to elementary school, my grandmother went to work
in the school cafeteria. So I would get up every
morning with her and we would go early because she
had to open up the cafeteria for school and all
the lunches. And that's where I first heard comfry music
was in her house that morning, you know, those mornings

(04:18):
getting ready to go to school.

Speaker 1 (04:19):
Who was born first, you or your aunt?

Speaker 2 (04:23):
My aunt Missy six days before me. She's six days
older than me.

Speaker 1 (04:28):
My Arkansas version of that story is my mom who
had me when she was fifteen, but her and her
sister married my biological dad, who I don't know in
his brother. So my cousins are double cousins, almost incest, yeah,
but not quiet, not quite. We're as close as you
can be. But it was two sisters and two brothers.
Oh you understand. Yeah, no one really got it. I

(04:50):
was like, we're double cousins. And they were like, does
that mean you do it with them? I was like, no, no, no, no,
you got the wrong idea. But you're not far off,
not far off. So what kind of country music did
you hear?

Speaker 2 (05:02):
Well? In her in her house, it was bluegrass. It
was it was just this.

Speaker 3 (05:06):
It was just this, this show on TV called the
kas Walker something our you know. He had a he
had a chain of grocery stores in East Tennessee. And
it's funny the things you remember, right because he had
a slogan, And I guess I can say this, but

(05:27):
the slogan was, you can beat our prices, but you
can't beat our meat, no way.

Speaker 2 (05:31):
Swear to God. I remember that as a child.

Speaker 1 (05:33):
That's true story. So I guess my question would be
because that's so funny, and it would not work now.
It wouldn't work now. Did beat our meat mean the
same thing back then?

Speaker 2 (05:46):
I didn't know what that even meant as a child
when I heard it.

Speaker 1 (05:48):
You know, I know, But do you think that was
a masturbation reference that like a joke?

Speaker 2 (05:51):
Then it possibly, I mean it had to have been,
I would think so.

Speaker 1 (05:55):
I think it would have had to have been.

Speaker 2 (05:55):
But these were adults that made up that were down
in the market.

Speaker 3 (05:58):
So funny, right, these were adults that were doing the marketing,
so they had to have they couldn't have been that.

Speaker 1 (06:05):
It's like if a frat had a grocery store.

Speaker 3 (06:06):
That's that's the kind of So that's where I first
heard this music with the three par harmonies and all
this stuff, you know.

Speaker 2 (06:14):
So, but that's It's.

Speaker 3 (06:16):
Funny though, what happens to you as a kid, or
these things that you think that are really insignificant when
they happened to you in your life, and then you
grow up and you go into your life and those
small things meant everything, you know, And that's that's the

(06:37):
way it is for me in several places.

Speaker 1 (06:39):
Whenever my grandmother was playing music for me, I thought
what she was playing was current because it's what I heard.
And it were a lot of gospel records like Andy
Grippa's Gospel Records, Ray Charles country music. Ye, a lot
of Johnny Cash because he was from Arkansas, the same
reason that I'm sure, yeah, you love people from Tennessee
or your hometown, like, but I thought that was contemporary

(07:01):
country music.

Speaker 3 (07:02):
Well, I heard a lot of you know. Of course,
Dolly Parton was from East Tennessee. And there was a
friend of my you know, of our family who I
still love his singing is a guy named Con Huntley.
Con Huntley was from Knoxville, and I still look up
to him. So those people taught me that or showed
me that it was possible for the things that were
rattling around in my head. Right. But growing up it

(07:25):
was kind of like you. I mean, I my mom
loved Alabama. She loved Merle Haggard, you know. And it
wasn't until I got into into high school that I
heard about Leonard skinnerd and I heard about Tom Petty.
And I didn't know the genius of Bruce Springsteen or
Bob Dylan or any of that stuff until I got
into college. Because my musical taste now is very diverse,

(07:48):
it's you know, but I can tell you that I
was always drawn to and curious about the people that
wrote their own songs.

Speaker 1 (07:58):
Were you musical in high school?

Speaker 2 (08:00):
Not really?

Speaker 1 (08:01):
You just played ball?

Speaker 3 (08:02):
I was, it was singing, so, but I was. It
was in college where I decided that, you know, my
mom and my aunt Sharon, my family saying I and
I did too.

Speaker 2 (08:12):
I just didn't know.

Speaker 3 (08:13):
I had no idea, Bobby, that I was going to
do this for when you said I was going to
want to make this my life, I was. I was
an athlete, My father was a coach. I thought that
I was going to be in some sort of an
athlete or do something in sports with my life because
I was very passionate about it, and I'm still passionate
about sports. Sports and music are two passions in my life.

Speaker 1 (08:34):
Then where did you sing as a kid? Like church?

Speaker 2 (08:36):
Church, school? But never? I mean I was in college
before I was.

Speaker 3 (08:41):
I had a guitar and I was sitting outside my
apartment complex my freshman year in college, and there was
a couple of people that lived, you know, like it
was outside. You'd walk outside and there was a you know,
it's just the outside part of our apartment and you'd
walk down to all the doors and you know, so
I would sit outside and people could hear me playing.
And there was a couple of people that said, you know,

(09:04):
there's a lot of people that plays at Chucky's Trading Post.
This is in Johnson City, Tennessee. There's people playing down
there every night at Chucky's Trading Post for tips, doing
exactly what you're doing right here at your apartment, and.

Speaker 1 (09:18):
You're doing it for free. It's basically what they're saying.

Speaker 3 (09:20):
You can do that, really, and it just kind of
sparked my imagination, and I called them to see if
I could come down and play for them. And actually
before that, I went to see what they were doing,
you know, and I was Me and my buddies went
there to eat, and I did I didn't even tell
my buddies what I was. What was really the purpose
of the trip?

Speaker 1 (09:38):
Did you have to go on play for them? Yes,
So I talked to somebody.

Speaker 3 (09:42):
I talked to a waitress that night, and then after
that she introduced me to the manager and I told
her what I wanted to do. I said, I want
to do that let that guy's doing up there, and
she goes, well, come here Saturday and play me some songs.

Speaker 1 (09:56):
When you do that, are you nervous?

Speaker 3 (09:57):
Because you have a very Because I didn't have a
lot of material, she asked me, you know, I played
her a couple of songs. I could see she was
looking at me and grinning, you know, and she goes, well,
how much material do you have? I said maybe an hour.
She goes, well, you're gonna need four. So I had
to get I had to learn some material.

Speaker 1 (10:15):
What do you what did you know then? What do
you think you would have played? Then?

Speaker 2 (10:19):
Well? I know what I played. I mean, I played
a lot of country music that I loved. I played.

Speaker 3 (10:25):
You know, George Straight, Randy Travis was was blowing up
at that time. I played a lot of ran I
played some Hank Junior, I played the Eagles, I played
Jimmy Buffett, I played just a random Leonard skinnerd I
loved them. I played a little bit of Bruce, even
though I wasn't that familiar with his catalog. There was
a couple of songs that I really loved, like one

(10:47):
Step Up, which I would end up recording years later
on the No Shoes album. I just played a lot
of a lot of stuff. And it was me and
a tip jar and a bunch of people that were
there to have dinner. But I didn't want them, you know,
they were having conversation. I wanted them to listen to me.
So I it was a glimpse into the future a

(11:10):
little bit because I would just I was really loud
in there, you know, and they had I got to
talking to a couple of times of management. Oh, they
didn't want you to be that want me to be
that loud? I said, well, I want them, you know,
to pay attention to me. And so I learned my
lesson there, had to turn it down some, but it
was it was truly a glimpse into the future.

Speaker 2 (11:29):
Cause if you come to our shows.

Speaker 3 (11:30):
In any any kind of environment, it's a it's it's
not timid.

Speaker 1 (11:35):
I want to come back to this exact point, but
it reminds me because you're going to do Sphere Part two. Yes,
So I didn't come out. I know I should have
come out.

Speaker 2 (11:44):
But.

Speaker 1 (11:45):
People aren't looking at you because you've built such imagery
and you're talking about like people. They didn't go to
listen to you. But it just it made me think
of this. It's ironic, right that you're in this Sphere
and you've built this entire career. One of the great
you're you're a current and a great at the same time,
which is wild because that is unique. Yeah, very unique.

(12:06):
But again, you've built this show to where people aren't
looking at you. I know, that's got to be weird
to even do that the first time, right.

Speaker 3 (12:12):
And you look at the beginning, it was weird, I'll
tell you, but they can't. You just can't help yourself
because it's it's such an emotional experience and a visual experience.
So you know, at first, you know, we're up there
playing and there's like I said, people are just like

(12:32):
they're processing what's happening to them.

Speaker 1 (12:34):
But that's weird for you because that's never happened to you, that.

Speaker 3 (12:38):
Not until until early not since early on in my career,
you know. But luckily, over the years I have you know,
learned how to control an audience and learn how to
talk to an audience, and slowly but surely, you know,
we were able to get their attention and pull them
across the fence to us and still have them see

(12:59):
what's going on. I mean us as a band, we're
doing it. You know, we're like the first the first weekend,
you know, to be up there in that space and
playing our music and we're just like, Wow.

Speaker 2 (13:09):
You're watching it. We're watching it too.

Speaker 1 (13:11):
Wow.

Speaker 2 (13:12):
Oh this is unbelievable.

Speaker 3 (13:13):
But that's what that's what makes Plansphere so incredible is
you know, when you go to a regular show, there's
the band and there's the audience, and some people even
put a sheer between the two.

Speaker 1 (13:25):
I don't like that.

Speaker 3 (13:26):
I say, come here, you know, we're gonna love on
each other all night. But still in a regular show,
there's there's a separation of the stage and the audience.
Playing Sphere, it's like we're all in there together. It's
just such a shared experience and it's hard to explain.

Speaker 2 (13:44):
And it took it.

Speaker 3 (13:45):
I think it took us the first three shows, like
and we're going to do it this year. We played
three shows a week. We did Wednesday, Friday, Saturday, and
I think it took us the first weekend to learn it.
And after that we were able to bring them across
the fence to us and and we're able to make
it as more of a normal show as it possibly

(14:06):
could because there is nothing about it normal. Everything is
so immersed and it's like, oh wow, the band, the crew,
then then there's the audience. And then there's the content
that is not just behind you, it's here, it's it's
over there, it's you could see it behind the crowd,
you know.

Speaker 2 (14:23):
So it took us.

Speaker 3 (14:24):
It took me a minute to focus, right, So, but
we're looking forward to it, you know now. It's it's
it's a much less learning curve this year because honestly,
you know, getting ready to do it and preparing all
the content and figuring out how it all works was there.
There was a learning curve to it, and now we

(14:46):
were preparing for it and we're going, oh, yeah, we
don't need to do this this this works better this way,
you know which, and we're changing you know, a third
of it because you know, there's probably going to be
some people come this year that came last year, and
it's like going to the circus every year. You want
to see different tricks.

Speaker 1 (15:04):
Back to the restaurant. Did you know when you started
playing the restaurant that that's what you might want to
do your whole life? Or did playing that restaurant make
you go, this is what I want to do my
whole life.

Speaker 3 (15:14):
It wasn't the restaurant I went wow, this is cool.
I was I had a tip jar and I would leave,
you know, with some cash in my pocket every night.
And I was in college and I was it was
at a Mexican restaurant, and I was getting free enchiladas
every night, and I was, I don't know, when you're
in college and you get a free dinner every every night.

(15:34):
I was playing four nights a week eventually, and then
it went from there to me playing in a real bar.

Speaker 1 (15:42):
Did you build a fan based on the restaurant? Yes,
like read regulars.

Speaker 3 (15:45):
So it's kind of like there was there was four
or five groups and bands in town. Uh, there was
a there was a there was a band called Plaine
Jane has No Date.

Speaker 1 (16:00):
There was a sounds like an alternative band it was
it was Yeah.

Speaker 2 (16:04):
And there was a group kind of it was kind.

Speaker 3 (16:05):
Of garage bandish group called Stinky Finger. And then there
was a couple of guys playing guitar. There was this
great guy named Alex Augburn who played everything, and I
was the country guy. Right, So I started to build
a little bit of a following. And but it was

(16:27):
in a bar called Quarterbacks Barbecue, and it had no
windows and it was about as big as this room.

Speaker 1 (16:34):
Right, did you play any songs that were your own
at this point, well, I mean, I like, did you
write any songs at the bar?

Speaker 2 (16:41):
I had.

Speaker 3 (16:41):
I had a couple of songs that I had written,
but I wasn't. I knew better, you know.

Speaker 2 (16:48):
Because I was.

Speaker 3 (16:48):
I was getting to a point where I was like,
oh wow, people were actually especially in the bar setting.
They they were listening and there were people in front
of me for the first time. And it was one
of those late nights of playing in that place, and
there was smoke everywhere and I didn't smoke, but I
would go home after playing these places and I would
smell like I did, you know, it was like in

(17:08):
my it was like my skin, you know. But it
was one of those nights where I saw a connection
with just a few people and they felt it, I
felt it, and they cared about what I was doing,
and I was I was learning how to do this,
and I was getting better at having I was, you know,

(17:29):
just getting better at all of it. And it was
one of those nights that I went, Wow, this might
be something that I might really this might be my life.
And look I was I thought I was. I was
a marketing major and I was going to do something,
you know with that. But I had no idea that
music was going to become.

Speaker 2 (17:49):
My life like this. Obviously, you know you can't dream that.

Speaker 4 (17:53):
Let's take a quick pause for a message from our sponsor,
and we're back on the Bobby Cast.

Speaker 1 (18:08):
What would you have done if you wouldn't have had
those nights that made you go, ah, I think it's music.
You're a major. What do you think you'd be?

Speaker 2 (18:16):
I don't know.

Speaker 3 (18:16):
I mean I think that I think on some level,
i'd be playing music somewhere. But I don't think if
if it wasn't my life, it would be, you know,
for fun, because that's what I still believe. Music is
still fun to me. Creating and playing music on stage
is still funded me. But it would be something I
think within sports it would be I don't I don't know.

(18:39):
I might be Bobby Bones, who knows, I might I
might be doing something in radio, or I might be
something we're doing, working for marketing for something for someone
I don't know I've Can you see how uncomfortable I
am on answering that because I really have no idea.
I mean, this was a godsend. I mean, this was
what I was supposed to do what I.

Speaker 2 (19:00):
Was put down here to do.

Speaker 1 (19:01):
Did you finish school?

Speaker 3 (19:02):
Yes, I got a I graduated East Tennessee State University
in Johnson City, Tennessee, in December of nineteen ninety.

Speaker 1 (19:09):
Then what happens right when you graduated? You move here?

Speaker 2 (19:11):
I moved to Nashville less than a month after that.

Speaker 1 (19:14):
So were you nash Are you planning to move here though?
After you graduated? Yes?

Speaker 3 (19:18):
And I moved I moved to Tennessee. I mean, I
mean I was in Tennessee. I moved to Nashville January thirteenth,
nineteen ninety one. And the reason I know that is
that's because that was the day the first Gulf War started.
Not W's not President W. George Bush, but his daddy.

Speaker 1 (19:38):
When we went in, was that all the on screw
se you saw like the bombing at night in Iraq? Yeah?

Speaker 3 (19:44):
Like I could that was happening when I first moved
to Nashville. It's funny, I didn't know anybody.

Speaker 1 (19:49):
I Yeah, what was it like when you moved here? Like,
what are the memories of you move into town?

Speaker 2 (19:53):
It was like.

Speaker 3 (19:55):
I think, I think, you know, my mom and my
family thought this was something that I was going to
do for you know, a little bit, and decide it
wasn't working and come home and get a job like
the guys that work with me out on the road.
Tim Hope, Daryl Hobby, and David Farmer, those guys. I
went to elementary school with them, I went to high
school with them. We were all college roommates. And they

(20:15):
have been on the road with me almost this whole time.
And David is my real manager, and Tim and Darrell
run my merch company, you know. But I think they
thought at the time that I was just going to
come home and get a job like them. But because
Tim and Darrell went to work for a Credit Union
and Classic and right, and I was, I was down
here trying to meet people and write songs.

Speaker 2 (20:37):
But I got a publishing deal pretty quickly.

Speaker 3 (20:40):
I mean.

Speaker 2 (20:43):
It was a little over a year.

Speaker 3 (20:44):
I got a publishing dealt at Acuff Rose Music, which
was eventually bought by Sony.

Speaker 2 (20:49):
But it was crazy, Bobby.

Speaker 3 (20:51):
All of a sudden, I was in town about a
month and I was playing down on Lower Broadway at
at a bar that no longer.

Speaker 2 (20:59):
Exist is called the Turf Covers again covers.

Speaker 3 (21:02):
Kind of like I did in college because I had
been doing that for two or three years in college
and once and then I got here. I got to Nashville,
and there was nowhere to do that unless you wanted
to go down there.

Speaker 2 (21:13):
And and.

Speaker 3 (21:16):
You know, get uh get it was an area of town.
Now if you go down the Lower Broadway. Now, you know,
every singer's got a bar. It's like, you know, there's
it's a bachelorette destination for whatever reason. It's it's much different.
It was well, I mean there was a there was
a yeah it was. It was dirtier and a little

(21:37):
more dangerous than it is now, but still it had
a lot of charm that built this town. And I
got to see that and I was down there. That's
what I did. But when I first got to town.

Speaker 1 (21:50):
Did you audition again there like you did at the
barbecue place? Yeah?

Speaker 3 (21:53):
But I I auditioned that afternoon and and sang that night.
So it was pretty wonderful.

Speaker 1 (22:01):
Was it another night of four hour sets?

Speaker 3 (22:03):
Yeah, I mean it was a yeah, it was forty
five minutes on and fifteen minutes off. I did that
four times and and so I would do that at
nine and I was able to write during the day,
and I would. I was parking cars at a couple
of places around town, uh, you know, working valets and
doing all that kind of stuff. But then when I
got when I got signed Aca Froze, it was all

(22:26):
of a sudden. I mean, it was bigger than life
to me because I was in the hallways and seeing
people that I truly looked up to, like you know,
Dean Dylon and Wade Schaeffer and Don Samson and Skip
Ewing and all these people that were great songwriters. And
I was in those rooms. I couldn't understand why, but
I was there, and that truly changed my life.

Speaker 1 (22:49):
When you're valeting cars here, did you valet for anyone famous?

Speaker 3 (22:55):
A lot of executives, right, I don't remember valeting or
anybody that was that was famous.

Speaker 1 (23:03):
No, Johnny Cashtrum, the truck, none of that.

Speaker 3 (23:06):
I think I think it wasn't his car. But Kenny
Rogers was in one of the cars that I did valet,
you know. But I remember a lot of the executives
would roll in and I would I would, I would
valet their car, and that was and I was used
to my mom's car and my grandmother's car, and then
the truck that I had that didn't have air conditioning
in it. Right now, I would I would get their

(23:28):
car and when I would valet it, I would go,
I go, damn, this this smells really successful, you know
what I mean?

Speaker 2 (23:36):
It was just different if.

Speaker 1 (23:38):
You drop off your car truck now, and I've had
this happen to me, especially when I've the first five
or six years here, people would leave music in my car.

Speaker 2 (23:47):
Oh, they that's happened to you?

Speaker 1 (23:48):
Oh yeah, Or if I'm eating dinner. Yeah, And I've
had it before where people would leave something like a
waiter and I would take time. I've brought them up
on the show before if they were good, and some
of them weren't.

Speaker 3 (24:00):
Right.

Speaker 1 (24:00):
But the problem with that was when I did it
and talked about it, then it created more of that.

Speaker 3 (24:06):
Yeah, yeah, that's the thing.

Speaker 1 (24:08):
I know.

Speaker 3 (24:09):
Has that happened to you as it in and now
it's more Yes, that's happened to me a lot, but
not in leaving leaving it in my car or whatever. Look,
my mom used to cut hair for a living, right,
so people would just come there and just drop off
stuff to her.

Speaker 2 (24:24):
I mean that was there. That was one way.

Speaker 1 (24:27):
You know.

Speaker 3 (24:28):
Now it's much different because they don't have to go anywhere.
They can just send it to you on social media.

Speaker 2 (24:32):
Yeah have you have you got?

Speaker 1 (24:34):
Yeah? So much so that it's everywhere all the time
that I don't see anything. People are always sending me
stuff because it's so much.

Speaker 3 (24:41):
Yeah, And I don't because I don't want to listen
to any of it because I don't want them to
come back at me and going, hey, I sent you this,
and you recorded some kind of similar, like in some
lyric that I didn't even write, you know what I mean?

Speaker 2 (24:51):
So I just I got my people.

Speaker 1 (24:54):
I had to buy insurance because when I started recording
comedy music, I had to buy insurance that said if
I get sued because I hear something, if somebody hands
me something and they sued me my business manager. And
again business manager was new to me much less having
to buy insurance for stealing somebody's song, and I thought
that was wild. But because I was taking and listening

(25:15):
to so much new music for one part of my career,
I had to have insurance to cover me in case
someone said, oh, I gave you this music and you
recorded a funny song and there's a couple lyrics in
that that you took. I thought that was wild.

Speaker 2 (25:27):
Now I get also that.

Speaker 3 (25:29):
Look, people are trying to build their own dream and
they're trying to find their way, and I'm like, I
was that person. But I don't think I ever left.
I mean I never left a CD and IRV Woolsey's
truck or his car.

Speaker 1 (25:42):
Did you think about it, right?

Speaker 3 (25:44):
I mean I didn't have to actually, because I was
a writer for a cuff Rose and then they had
people to take to walk it across the street and
give it to Irvin George or whatever, you know. But
I understand why they're doing it. But to this point
now it's just so it's such the wild, wild West
out there. I can't I don't ever listen unless it's

(26:06):
given to me by people that I really trust.

Speaker 1 (26:09):
When you move here, But when you got a publishing deal,
did you come with a bunch of songs?

Speaker 3 (26:13):
Yeah? Like that they weren't refined at all. I mean
I had to learn, you know. Look, I learned from
Afar Like I loved songwriters, and I learned so songwriting,
and so I when I first started writing songs, and
then I started looking at a lot of the people

(26:33):
that I loved who were songwriters, and their songs. I
realized that those were a lot more, a lot more
well crafted than what I was doing. Mine was like,
I'd write a song about a girl and it was
seven minutes long, you know, and I realized, you know, Okay,
that doesn't work. That's not going to work if I
want to do this, you know. But I one of

(26:54):
the first people I met in Nashville. There were a
few people that really, you know, gave me a lot
of great advice. And that was Klay Bradley at BMI
at the time, and he's there now. A guy named
Tom Collins. There was a guy named Jeff Gordon, not
the not the NASCAR driver, but there was a guy
that worked at MCA named Jeff Gordon, and I was

(27:14):
able to go and play him songs. And then there
was a girl that really became a huge part of
my record making life. Her name was Renee Bell and
Renee Bell and I made almost every record that people
have heard in my career. And those people were able to,
you know, give me a lot of direction when I

(27:37):
first came to town, which was a blessing. Not everybody
has that, you know, but they I think they could
see how much I wanted wanted it, and I think
they could see how much I loved creating and how
much I cared about songwriters and songs and I still do.

Speaker 1 (27:53):
When you moved here, did you play any like rex
softball leagues or any like, because you're an athlete. And
when I moved here, it was like, how do I
find people that by way? I I didn't know. You
gave it, they gave that all up played.

Speaker 3 (28:03):
I think, yeah, well really, I mean, I love sports
so much, and that's the thing. One of the things
I missed the most, Like me and my buddies out
on the road, you know, one of the one of
the things that we have that we feel very grateful
and fortunate for is we're out there on the road
and you're on the bus outside of the Pittsburgh Steeter
Football Stadium.

Speaker 2 (28:23):
We were, Wow, this is amazing.

Speaker 3 (28:25):
You know. We would go in and play all these places.
And when I played the Rose Bowl in Pasady in California,
I brought my dad and his buddies out there because
I can't tell you how many times I've sat on
a couch a lot like this, went and watched the
Rose Bowl with my father, and now all of a sudden.
I'm a small part of that history, you know, through music.
So we have we've talked about the thing that that

(28:48):
we missed the most, and the thing that I miss
a lot is competitive sports. I don't have that much
in my life anymore. You know, Uh, maybe one day
I'll I'll get on church softball team or something.

Speaker 4 (29:01):
You know.

Speaker 1 (29:01):
I started playing pickleball, and I started competing at pickleball.

Speaker 2 (29:04):
Well, I got a lot of friends that play pickleball too.

Speaker 1 (29:06):
Do you like that I need to compete at something? Yeah,
Like I love to play ball, and so pickleball you
could pick it up pretty easy. I'm still pretty athletic.
I was playing tournaments. I was driving, and I was
playing in like three point five tournaments, which is a
pretty high level. Not the hets, but pretty high. And
I tore my ankle. So it's like my age met recently. Yeah,

(29:29):
I just got out of a boot. Oh yeah, so
it's awesome. But I'm like that I need that fulfillment.
I need to compete. I was playing when I moved here,
like found a Rex softball league to play. I was
playing just trying to find that and I wanted if
you still tried to find yeah, maybe I should do that.
You shouldn't now, No. Yeah, I've been in a boot
and on a scooter for like four months. It sucks.

Speaker 3 (29:49):
Well, you know, I work out a lot, but especially
when I'm training to go on the road. I worked
out with the same guy for a long time. And
are you a yoga yoga guy?

Speaker 1 (30:00):
No, you don't do yoga.

Speaker 2 (30:01):
I've done hot yoga.

Speaker 1 (30:02):
Yeah, okay, I like it.

Speaker 2 (30:03):
I love how you feel when you get out of there.
I feel so depleted.

Speaker 1 (30:07):
I've done hot yoga too. I guess that's still yoga
to me. It's not yoga to you. That's insulting to
say yoga if you do hot.

Speaker 2 (30:12):
I mean, I guess it's a form of yoga, right.

Speaker 1 (30:14):
Isn't it the same?

Speaker 3 (30:15):
Just it's just I don't think it's Maybe I'm wrong.

Speaker 2 (30:17):
I don't know. I'm not the yoga expert.

Speaker 3 (30:19):
But I think when I I have a great group
of friends in Malibu where that's a more healthier of
a group than I have in my life in other places.
And I've done and I've done uh yoga with them,
and it's much it's harder to me than doing hot yoga.

Speaker 2 (30:40):
How yoga?

Speaker 3 (30:40):
I mean I'm sure there's a lot of poses and
stuff that that's.

Speaker 2 (30:43):
That's part of yoga, but.

Speaker 3 (30:47):
It didn't seem as difficult to me, and I maybe
completely wrong. Maybe it's because I'm just so hot in there.
I don't it doesn't seem so good. But yeah, I
in any way that I can get where you can sweat,
and I heat and ice all the time.

Speaker 2 (31:01):
I do a sauna.

Speaker 3 (31:02):
I do fifteen minutes in the sauna and I do
about I'm working my way back up to three minutes
in the ice, which is hard for me, but you know,
being I'm fifty seven now, So anything that you can
do to get toxins out of your body and help
your body heal, you know, especially from working out as
hard as I do, it's it's great.

Speaker 2 (31:23):
And especially when you're on stage.

Speaker 3 (31:26):
When I'm working out there, you know, I beat my
body up.

Speaker 1 (31:30):
Do you ever get really gassed out there?

Speaker 2 (31:32):
Well, yeah, especially if it's if it's human, you know.

Speaker 3 (31:36):
But that's one of the things that I One of
the reasons I train so hard is but is just
for my cardiovascular you know, to be in shape for
that because if you're out there, I can't help it.
I have video footage in my grandmother's kitchen of her
and my mom and my aunt Sharon and my aunt Missy,

(31:56):
all of them listening to music. And I'm Bobby. I'm
telling you, if you look at that video, I'm moving
the same way as a child as I do on
stage as an adult. It's the same move, the same stance, everything.
But I can't help it.

Speaker 2 (32:12):
So when you have the.

Speaker 3 (32:13):
Band that I have and the drummer that I have,
and the guitar players and all of it, I move,
and so I have to be That's the thing I
am in constant thought of thinking about. Okay, it's one
thing to train and be in shape and you know,
to get in what I call my show jeans, right,
But it's another thing to be up there in the

(32:35):
moment feeling all that energy and the rush of the
audience and the band and those two energies and synergies meeting, okay,
and you not feeling overwhelmed, and so you can sing
in the middle of it. And that's what I train
for is and that's something you can't simulate on a
treadmill or in the gym or anywhere. It's just got

(32:56):
to you gotta work your way through it.

Speaker 1 (32:57):
Do you ever do the merch lottery with your guys?

Speaker 2 (33:00):
Did merch lottery for a long time, can you?

Speaker 1 (33:02):
We explained that, well, I.

Speaker 2 (33:05):
Did merch lottery.

Speaker 3 (33:06):
I don't know, it's four or five years in a row,
and it was I started doing it the first year.
We were playing football stadiums across America, and I went,
you know what, I'm gonna like, these guys are out
here working really hard, and I've decided that I was
going to pick one stadium show on the tour and

(33:28):
whatever was made that night, we're going to do a
merch lottery. And we we When I played Sammy Hagar's
birthday party one year, he gave me this.

Speaker 2 (33:38):
He met me and the band.

Speaker 3 (33:41):
At the airport and gave us all sambreros and had
had trays of tequila shots. He met us at the airport,
you know, and he goes, happy birthday to me, and
so here we are in the We're going through customs
and doing tequila shots on sombreros. It's great, you know.
So I wouldn't take anything for that brero, you know,
I had it. I caught a blue marlin off the

(34:03):
North Drop in the Virgin Islands, one year and and
had it, you know, took it to the taxidermist, and
so we still have it out on the road and
I have that sombrero Sammy gave me on top of
that blue Marlin. We've had a road case built built
for it and everything, and it's still out there. So
I decided we were going to It's almost like drawing
names for Christmas, you know, So we put everybody's name

(34:24):
on a piece of paper in that sombrero, and we
brought everybody together and I would go out there and
shake it all around and pull out a name, and
whoever's name I pulled, got all the merch for the
stadium that night, all the money, all the money, all
the all the merchandise. Would that which could be life
changing money. It's six figures really.

Speaker 2 (34:44):
Yeah.

Speaker 3 (34:45):
So what they ended up doing, though, is after a
couple of years, whoever got them most to say, you
got the money, you know, you're you're you're part of
the video crew. And I pulled out Bobby Bones's name right. Well,
what they started doing is just sharing it with everyone,
which was great. You know, they split it up amongst everyone.

Speaker 1 (35:08):
So the first couple of years, though, someone would win,
like two, three hundred thousand dollars.

Speaker 3 (35:12):
Yeah.

Speaker 5 (35:13):
Wow, the Bobby cast will be right back. This is
the Bobby Cast.

Speaker 2 (35:30):
What if?

Speaker 1 (35:30):
Because that were my That makes me think of like
those lines at Starbucks where they keep passing it on.
What if somebody didn't share it? It's like two years
and then gym wins and he's like, screw this, I'm
keeping it. Yeah. Well, I mean that happened a couple times,
Like somebody that cuts off the Starbucks pass it online.
You're like, oh, they didn't know they had to share it.
You know, that was part of the thing.

Speaker 3 (35:50):
Oh, you know, somebody's life could you know, be changed whatever.

Speaker 2 (35:55):
But then then they.

Speaker 3 (35:55):
Decided, oh, well you know what, all of our lives
are going to change little bit.

Speaker 1 (36:00):
Yeah, that would be crazy to win the merch lary.

Speaker 2 (36:03):
I know. I yeah.

Speaker 3 (36:04):
When I first did it, I was like, all my
buddies are going, you sure you want to do that?

Speaker 2 (36:07):
Yeah, I'm sure. And then then we did it.

Speaker 1 (36:12):
It's like, okay, you put your own name in it. Yes,
you moved to town. How long until you actually have
but think about that, Think about moving the town and
not even not having anything to a point where oh
you're doing merch law. Ye, how long until you get

(36:34):
any sort of as an artist, any sort of traction.

Speaker 2 (36:38):
Well, I when.

Speaker 3 (36:39):
I got my my songwriting deal, first with a Coach Froze,
and then that was It was about a year and
a half later that I saw my first deal with Capricorn.

Speaker 2 (36:53):
Records.

Speaker 3 (36:53):
But that was that was a lot like playing you know,
Triple A baseball. I thought I was in the major leagues.
My family thought I was.

Speaker 1 (37:02):
In a major record label.

Speaker 3 (37:03):
You're saying, yeah, like yeah, being on that, you know, because.

Speaker 2 (37:06):
I didn't know.

Speaker 3 (37:07):
I was so green and oblivious. I thought that I
had a record deal, and I did, but it was
it was a it was getting to learn things, and
I'm so grateful for it. But I was not competing
I would I wasn't even on the same playing field
as the major labels, you know. But it gave me
an opportunity to go out on the road. I had
a band, I was growing an audience barely. I was

(37:29):
selling a little bit of merchandise, you know, I was.
I was learning and and it was not until after
the There's a guy named Joe Galante who was running
RCA in New York, and he signed Dave Matthews and
he signed a lot of people that we all know
and love. But he came back to Nashville to run
the Nashville division and I was one of the first

(37:51):
people that he signed.

Speaker 1 (37:52):
How did you get out of the Capricorn deal?

Speaker 2 (37:55):
That I went and asked off of it?

Speaker 3 (37:58):
Because you knew there was I was, and I knew
we weren't going to and I learned, you know, very
quickly that I was on an independent if you will
record label. Now it was a very big label out
of making Georgia. I mean, they had a lot of
big acts on there, and I to this day, I
am very thankful for Phil Walden and everyone involved in that,

(38:19):
because you know, you get to a place in your
life and you know that every single part of it
is for a reason, and that is no different.

Speaker 1 (38:28):
Do they keep a little percentage of the Kenney after
you left?

Speaker 3 (38:31):
Well, it wouldn't. They didn't let me go for free.

Speaker 1 (38:33):
Yeah, so we had to, you know, to Phil's credit.

Speaker 3 (38:38):
You know, I went in there and Phil knew what
I was coming to talk about, and he was nervously
moving some papers around and he goes, what's going on?
Can you tell me something good? And I said it
was in the fall. I said, well, Tennessee play Saturday.
That's good and and I said, Phil, you know we're
not competing, you know, I said, please let me off

(38:59):
the label, you know, so I can go and pursue
something else and I'll never forget it. He goes, Kenny,
I signed you because I believed in you, and I'm
letting you go because I believe in you. He goes,
Have the lawyers call me and we'll.

Speaker 2 (39:15):
Work it out. I went, okay, great.

Speaker 3 (39:16):
I didn't care what the details were. I was out
that door very quickly. But yeah, it wasn't for free,
but it changed my life.

Speaker 1 (39:24):
When you started having hits, do you feel like those
hits are still in the same vein of the music
you make now?

Speaker 4 (39:28):
Now?

Speaker 1 (39:29):
The reason I asked, we're doing this documentary type series
on the nineties in general. Yeah, and I think we
talk about you a lot in ninety seven, and that
may be when you uch first number one. Yeah, but
it also that music, as awesome as it was, it
doesn't feel like the same.

Speaker 3 (39:45):
Kenny, Well, it's sonically much different. And I was making
music in the night. Look, I was just trying to
get on the radio. So I was trying to be
anything that was successful. I had no idea who I
was as an artist. I had no idea where this
was going to take me. I had no idea. I
didn't I was so green. I was just making records

(40:06):
that I thought would get played. And some of those
records I'm proud of today. Some of them I'm not.
But when you do this a lot, you start to
grow as And I've co produced almost everything that I've
ever done. I did that with Barry Beckett, and me
and Buddy Cannon have made all the records since then.
But sonically it's a much different well, it's a much

(40:29):
different time in our genre in the music worldwide. But
if you listen to nineties country Kenny and then you
can see the progression sonically. And I think that the
song since got better. And I remember having a coming
to Jesus meeting with myself and I said, you have
to be better. You have to be better. The songs

(40:52):
have to be better, the production has to be better.
You as a human being, you have to be better. You.

Speaker 2 (41:03):
I'll never forget it.

Speaker 3 (41:04):
I was in my apartment complex out east of town
and it was one of those epiphany moments and I
had a list of things on a yellow note, on
a yellow legal pad, of things that I could change,
that would that needed to happen for me to go
to the next step, and I started working on that list.

Speaker 1 (41:24):
Did you ever feel like you wouldn't make it? Did
it ever get so bleased that you're going I think
this may not work out? Yes?

Speaker 3 (41:29):
I mean, well even so, Okay, so after Capricorn, you know,
Joe signed me to a major label deal and it
wasn't working.

Speaker 2 (41:38):
You know, we had a few hits.

Speaker 3 (41:39):
I had a few songs and that that you know,
got into the top five, and and but look, Bobby,
I had What's crazy, What is really crazy about my
life and my career is I had an eighteen song
Greatest Hits album and nobody knew who I was.

Speaker 1 (42:00):
So then why did you make the greatest hits if
they weren't that great?

Speaker 3 (42:03):
Because we had the songs and it was honestly, it
was a marketing move by the label. Okay, now, okay,
none of these are really successful, so we're just going
to bunch them all together and make it successful. We
went double platinum on a bunch of songs that weren't
that successful.

Speaker 2 (42:18):
So that's a true story.

Speaker 3 (42:20):
And then that led me into the where that it
was during that period that I went, Okay, we have
to make this better.

Speaker 1 (42:28):
So you had the Greatest Hits album that launched your career,
like we didn't super charge it.

Speaker 3 (42:32):
I would say it was double platinum. We sold two million.
Greatest Hits were records, you know. And but that gave
me time. And there was about about a two year
period from when the Greatest Hits package came out to
whin the no Shoes, no Shirt, No Problems album came
out that completely changed my life. And because the music
had changed, I had changed mentally, I had changed physically.

(42:56):
I was in shape, I was my brain was on
fire with creativity, and.

Speaker 2 (43:02):
It just changed.

Speaker 1 (43:03):
Yeah. I was gonna ask if you ever had a
tough love yourself. It sounds like you were doing that
to where they're probably decisions you have to make. If
I'm going to be better, I have to stop. And
I don't know. It could have been drink.

Speaker 2 (43:13):
I mean it was it was.

Speaker 3 (43:15):
I changed my diet, I changed my I don't know,
I uh, I gave all of it.

Speaker 1 (43:22):
Are there any songs that you recorded back then that
you don't like to play now there were number one.

Speaker 2 (43:28):
Yeah, I mean I don't.

Speaker 3 (43:30):
I wouldn't say don't like to play. You know, we
still do. Don't happen twice on the show, and for
whatever reason, it still fits in our show, we do
tractor every now and then. Just now, there's a moment
that I got really sick attractor, Like I just said, wow,
if I don't have to sing tractor anymore, it's not
going to hurt my feelings. But then Mega Maroney comes
out on the road with us, and she's out there

(43:53):
for a couple of weekends, and she goes, why are
you not antractor?

Speaker 2 (43:55):
I want to hear tractor?

Speaker 3 (43:56):
She was, everybody out there wants to hear a tractor.
I want to hear tractor. And I said, okay, well
you're about to come up and sing it with me,
and she goes, deal, and then I did it, and
she was right.

Speaker 1 (44:07):
They go crazy, they go crazy.

Speaker 3 (44:09):
It's just it's like, okay, me mentally, I'm passed it,
but it's it will forever be there, you know. And
that's when she and I became started to become really
good friends, you know. So but that's how I started,
That's how I started playing tractor again. It is because
Megan more or less forced it on me.

Speaker 1 (44:28):
I think she for sure my favorite. I think she,
if not the best, is one of the best new
in this new version of greats. I think she's one
of the best songwriters that exists.

Speaker 2 (44:39):
I think that she has a.

Speaker 3 (44:44):
You know, I've had the luxury of being around her
now for a couple of years and getting to know her,
and she has a very unique work ethic.

Speaker 1 (44:54):
She has.

Speaker 3 (44:56):
A very unique song since. She has an unbelievab personality,
she has an unbelievable sense of hearing.

Speaker 1 (45:03):
She's so funny. I was about to say that she's
so funny.

Speaker 3 (45:05):
And not everybody. I mean, you have to really get
to know her and peel the onion back to see
how thoughtful she is. I mean, she's just an amazing
human being. And but there's a work ethic in there
that early on that I recognized that makes sense, you know,
And that's how we became really good friends out there,
you know, And so over the over the course of

(45:27):
the twenty twenty four summer tour, Megan and I became
became very close, you know, and I mean we're it's
we played the Atlanta Falcons Football Stadium in twenty eighteen,
and she was a college kid up in the three
hundred section with her friends.

Speaker 2 (45:45):
Now, think about how powerful the universe is.

Speaker 3 (45:48):
And if you would have told me on stage that
night that you're you're going to become really great friends
with a person up there, you know, I told you
you're crazy, But that that happened, you know, And to
see what's happened to her, and to see her take
it and run with it, and to see how speaking
I told you earlier that my brain was on fire,
I recognized that because her brain is completely on fire

(46:11):
with creating music and giving her audience positive energy and love.
And it's it's been really interesting to see what happened
to us. It's it's happening to one of your friends,
and I get to watch it, you know, from the
side of the stage.

Speaker 1 (46:28):
Just let that though, when you who were you in
the crowd for that was that? Well, later on you're
the kid and I got to know, yeah, And but
you were watching them at a show and again, same
thing happens. It's like, holy crap, I'm on stage with whomever,
or I'm friends with whomever.

Speaker 2 (46:42):
Well, when I was in.

Speaker 3 (46:46):
When I was in high school and I went to
see Jackson Brown by myself because I was I loved
that music and I was beginning to think about, you know,
how much I love songs and whatever. And I went
to see Jackson Brown, never knowing that I would meet
him ever. Right, I went to see George Straight, never
knowing that I would ever be on the road with

(47:07):
George Straight ever, and I was. I That's how I
got introduced to the world of doing stadiums. I was
out there two summers in a row with George and
it changed my life. But I now, of course, you
never can think that, you know, But I think it's
very interesting. I think people are pushed into our lives

(47:31):
for reason in and out, you know, and it's it's
I think, you know, it's just the universe works in
crazy ways, and to see that what's happening to Megan
is is beautiful. But also, I mean, the one that
really comes to mind is when I first moved to Nashville,
I had zero money. I was living with a friend
that I was in a bluegrass band with in college

(47:52):
off of Belmont, Okay. She let me stay in her
house because I had nothing. It was right before I
signed with a coach Fro's Music, and a lot of
my friends were going to go see Jimmy Buffett at
which is no longer there at a place called Starwood Amphitheater,
and I went to see Jimmy. It was pouring rain
that night. We went in a party bus and I

(48:17):
went home that night and I was lying in bed
and I was staring at the ceiling, going what did
I just see. I'd been to a lot of concerts,
but I never saw somebody love their audience quite like that.
And it made an impression. Right now you fast forward.
That was in nineteen ninety That was in the summer

(48:37):
of ninety one. Now you fast forward twelve years. Right,
whatever it was when I first met Jimmy Buffett, I went.
I was with my friend Holly Gleeson and she had
a friend in Palm Beach that knew Jimmy and we
were playing in Vegas at the same time. Jimmy was

(48:58):
playing across the street at the end GM and I
was playing. This was right when my life changed. And
I was playing the the UH the arena at Mandalay Bay,
and we walked over UH and there was Jimmy and
some of his you know, road family with him at
the pool at the Four Seasons in one of those cabanas,

(49:18):
and I walked up and I went, there's the guy
that I saw play in the pouring rain in Nashville,
you know, and never knowing that I would become friends
with him and collaborate with him and be in the
studio with him and become friends with him and get
to know him on any level. So that was That's
kind of a my.

Speaker 2 (49:39):
Version of me and Meghan, if.

Speaker 4 (49:41):
You will, let's take a quick pause for a message
from our sponsor, and we're back on the Bobby Cast.

Speaker 1 (49:57):
Do you ever just go to Sonic or Chick fil
A and order something and they look at you like,
there's no way Kenny Chesney's ordering Sonic or Chick fil
A by himself.

Speaker 3 (50:05):
Well, I mean it's been a minute since I went
to Sonic or Chick fil A. But I do love
when I was eating Chick fil A.

Speaker 2 (50:11):
I love the sweet tea. I did love that when
I was drinking that stuff.

Speaker 1 (50:14):
But cheesecake fact anywhere anywhere, anywhere, not specific, but just
in there. Yeah, I mean, like, why is Kenny Chesney
at a gas station in Tupelo Mississippi. It just random.
Do you ever just do that? You ever buy yourself
in normal places?

Speaker 3 (50:29):
Yeah? I mean I go to normal places. I mean
I can walk between the rain drops pretty well. No way,
grocery store kind of well, it's been a minute since
I've been to a grocery store, but I go early.

Speaker 2 (50:39):
If I go to the grocery, where do you go?

Speaker 1 (50:40):
That's so normal that we'd be like, there's no way
Kenny Chesney goes there.

Speaker 2 (50:44):
Oh well, I don't know.

Speaker 3 (50:46):
But I mean I've been I've been at gas stations
or whatever, or you know, I would be at a
at a.

Speaker 2 (50:53):
Restaurant, you know, whatever it is.

Speaker 3 (50:54):
And I remember this guy recently and he's, you know,
him and his wife are staring at me. I got
raid are pretty good, you know, and I could just
tell okay, well you know there, or if my phone's
up at the attention ever was when they could do
it backwards, make an act clock and you know whatever,
but he could.

Speaker 2 (51:12):
He finally comes up to me and he goes, you're him,
aren't you?

Speaker 1 (51:18):
I said, what.

Speaker 2 (51:18):
Depends on who you're talking about, you know, but you
know what usually I mean, look, yeah, when.

Speaker 1 (51:27):
What about traffic? If someone looks over. You ever see
people look over and try all the time and they're like,
it's all Jesny and traffic.

Speaker 3 (51:34):
But when people come up to me, and I mean
nine times out of ten, it's pretty positive. You know,
I haven't drank in a while. So when especially if
I went on Island or down South and they you know,
back when I was really partying a lot and people
would want to picture and I would say no, I mean,
I can't see your camera.

Speaker 2 (51:53):
You know, I'd rather not take a picture.

Speaker 3 (51:59):
But but now, I mean, there's worse things that people
could say to you than I love your music. And man,
that's what happens. We just wanted to tell you that
we love your music, and there's a lot worse things
people could say to you.

Speaker 2 (52:13):
That means a lot.

Speaker 1 (52:14):
I only got a few more minutes with you. But
people bring their best, their favorite or one of the
records that influenced them the most. And we talked about
Jimmy Buffett. Is that a Jimmy Buffer record over there?
That's it? Would you mind holding that out by telling
us why you picked this record?

Speaker 3 (52:30):
Well?

Speaker 2 (52:30):
I picked this record, and it's interesting.

Speaker 3 (52:31):
We talk about the greatest hits or a compilation, because
I believe this is a compilation, you know, what is
it which records the songs you know about heart And
this was one of the records that captured my imagination.
I say this a lot about my friend Jimmy Buffett.
He was one of the first people that taught me
it was possible to paint pictures with words, and it

(52:53):
took my brain somewhere else, a kid from East Tennessee
that didn't know that it was possible to sit on
that boat somewhere that boat. It just it was. This
music really meant a lot to me. And this album,
you know, because I you know, the first time I
heard Pirate looks At forty, which is still one of
my favorite songs ever, I played Pirate looks At forty

(53:15):
because just the story of it, you know, It's just
I played that song on a stool with a tip
jar and a lot of different places, and I don't know,
I just I truly loved the storytelling. I love the
simplicity of it. I love how it took if it
can take a kid's imagination from East Tennessee anywhere, you know,

(53:36):
this was one of the albums that I feel like
that that you know, built Jimmy's life, you know, and
it sure made me curious about what was out there.

Speaker 1 (53:46):
Do you think about mortality ever?

Speaker 2 (53:49):
Well, I mean not recently.

Speaker 1 (53:51):
I mean I mean no, when I heard Pirate looks
at forty, well no, that's a yeah, that's what I think.

Speaker 3 (53:57):
Yeah, No, not really.

Speaker 2 (54:03):
Okay, I wow, I'm mam now I will tonight, fair enough?

Speaker 1 (54:17):
What do you want to be remembered for?

Speaker 3 (54:18):
Then? Oh? Wow? Yeah? I mean I guess legacy is
only what people think about you, right, I don't know,
do you care?

Speaker 1 (54:27):
Do you even care?

Speaker 2 (54:29):
I think everybody cares.

Speaker 1 (54:30):
I don't care that much. But I don't have kids yet.

Speaker 2 (54:32):
I don't have kids either, so I think it's still
like I don't know. I think somebody that that.

Speaker 3 (54:43):
Loves spreading positive energy and love to their audience, that
loves songs and songwriters that you know, love the ocean,
love protecting it, loved, so that's.

Speaker 1 (54:55):
Become important to you, protecting the ocean, sure, environment?

Speaker 3 (54:58):
Yeah?

Speaker 2 (54:58):
Yeah, and yeah, I don't know.

Speaker 3 (55:00):
Like people people have asked me about legacy, you know,
and I think that it would be important for people
to know that. I because somebody asked me in an
interview once they said, we think it's great that you
give so much of yourself to what you do, and
I stop them. I said, no, no, no, I give
all of it. So I think that that would be

(55:22):
a part of it. You know that I truly have
given almost all of myself to do what I do.
But I but it never wants I swear to God.
It's never once seemed like sacrifice. I truly loved and
love what I do. I love creating. I love the
look on people's faces when I'm up there and I
know I just played their favorite song.

Speaker 1 (55:43):
I know it is unless this tractor and you tractor
and whatever. All right, three final questions. Okay, growing up
without a lot, Now you've done quite well for yourself.
What's the coolest part about being rich that you didn't know?

Speaker 2 (56:00):
That you can help other people?

Speaker 3 (56:03):
That?

Speaker 1 (56:05):
I mean, such a good answer.

Speaker 2 (56:07):
I mean, you can help other people.

Speaker 1 (56:08):
I wanted you say an airplane.

Speaker 3 (56:10):
Well, that's that's a perk. That's that's that's you can
help other people with that perk.

Speaker 1 (56:15):
Okay, got it?

Speaker 2 (56:16):
Which we did.

Speaker 1 (56:17):
Yeah, after.

Speaker 2 (56:19):
We saved a lot of animals.

Speaker 3 (56:20):
Like being able to help you know, I, I uh,
that's the that's the best thing about being blessed, you know,
with with what's happened to me is being able to
help people that need help.

Speaker 1 (56:35):
Final question two of three. Of all of your songs,
which song ended up being a monster that maybe you
didn't quite think it would be? And I'm sure you
have confidence in all of that.

Speaker 3 (56:49):
Yeah, but one that surprised me was Save It for
a Rainy Day? And I don't know that it was
the biggest hit, but I didn't. I mean, it was
it was on brand. I knew when I heard it
that it was on brand, if you will, and that
it might be fun live. But when we kick into
that today, I went, oh wow, I mean that was
a real hit.

Speaker 2 (57:09):
There's that one.

Speaker 3 (57:11):
What I mean the first time I heard when the
Son goes down and went, oh, yeah, that's going to work.
I don't know that it's going to be an eight
week number one, which it was, but I didn't know
it was going to be that. That surprised me, but
I knew it was going to be, you know, good
for us. You went tequila. I didn't know what it
was going to do. But that song didn't even go
number one. I had more number two records than probably

(57:33):
any act in the world. I mean, I've had like
fourteen or fifteen songs that didn't hit number one that
was number two, like no Shoes, no Shirt, no problems,
went to number two that.

Speaker 1 (57:43):
Wasn't a number one Nope, and.

Speaker 3 (57:46):
It got stuck behind my friend Jimmy Buffett and Alan
Jackson's five o'clock somewhere for eight straight weeks.

Speaker 1 (57:55):
Wow, that's just bad time. The same label pissed me off.
Oh ok, because they didn't make the call to go
pull that one back.

Speaker 2 (58:04):
Let's do a little bit. But that record was so
hot they couldn't maneuver it.

Speaker 3 (58:07):
You know what I mean.

Speaker 1 (58:08):
You in Tequila is a top five all time song
for me.

Speaker 2 (58:12):
Thank Yeah.

Speaker 1 (58:12):
It's not a top five Kenny song, like a top
five all times oh thank you.

Speaker 2 (58:16):
I mean that song was.

Speaker 3 (58:21):
You know, I had that song recorded, but I didn't
know who I wanted to sing on it, and I
didn't want someone expected within the format. Was nothing wrong
with that, I mean, that happens all the time, but
I felt like that song was so special and little
left the center for me. You know, I felt like
that You in Tequila you could be in an uber

(58:43):
or a taxi or your own car. Somewhere in Italy
or wherever in the world, and that song come on
and it fit, and so it needed the voice, the
perfect female voice to be that the ying andy of it,
you know. And when I heard Grace Potter, I went, oh,

(59:03):
my god, that's the voice. I never met her, and
I sent her You in Tequila, And less than three
days later after I sent it to her, she was
in Nashville on my birthday, marsh the twenty six and
we were in the studio recording doing our vocals on
You and Tequila.

Speaker 1 (59:19):
When you recorded it, do you think you'd be a single?

Speaker 2 (59:21):
Didn't know if it was going to be a single. No,
I had no idea.

Speaker 3 (59:24):
It was part of the Hemingways Whiskey album and we
had no idea what was going to be the first
single ended up being Boys of Fall was the first
single off that because we released it in late summer.
But You in Tequila as one of my top five
songs of mine.

Speaker 1 (59:41):
Oh that's what I'll do. The final question, then do
your top five songs of you? You do your top
five five to one or one to five. It's probably
easier to go one to five, right, but it changes.

Speaker 2 (59:49):
I mean, it's like it like you could ask me tomorrow, but.

Speaker 1 (59:51):
You can't, Okay, but I'm asking you today and you
open that up because to day I want one through
five Kenny Chesney doing Kenny Chesney songs.

Speaker 2 (59:57):
Number one, number one. Probably it would be.

Speaker 3 (01:00:04):
Old Blue Chair, just because it's such it's such a
portrait of my soul.

Speaker 1 (01:00:11):
It's it was.

Speaker 3 (01:00:12):
It stamped a time of my life where I was
in the Virgin Islands and man, I remember I was out.

Speaker 2 (01:00:19):
This was remember, and I started writing this song at.

Speaker 3 (01:00:23):
The writing New Year's Day, well, New Year's Eve, whatever
it was. It was in nineteen ninety nine. There was
this this person I forgot the name, that the name
god that did this. But he predicted that the world
was going to end at the at Front at the
year two thousand.

Speaker 2 (01:00:41):
So everybody was just kind.

Speaker 1 (01:00:42):
Of like Y two K was also going to kill everybody. Yeah,
like not, what what's that was?

Speaker 2 (01:00:48):
Yes?

Speaker 1 (01:00:49):
Oh, I thought it was like somebody you knew.

Speaker 2 (01:00:50):
No, I didn't know.

Speaker 1 (01:00:51):
It was like freds of years after my uncle. Oh yeah,
that was like I thought it was like Cress at
the Credit Union. Again, I didn't know.

Speaker 2 (01:00:57):
Yeah it was not Michael, but yeah, gotta gotta got it.

Speaker 3 (01:00:59):
But so everybody, the whole country was, the whole world
was kind of okay, well this is gonna be weird.

Speaker 2 (01:01:06):
And I thought, well, that's gonna happen. I want to
have fun, you know.

Speaker 3 (01:01:09):
So I was. I was down in the Virgin Islands
and I was, I was, you know, having a blast.
And the place that I rented had two blue wicker
rocking chairs, and I stayed there for like three or
four years. And I remember I came in from town
and I had I had a cup that tall full
about you know, coconut rum and diet coke, and I

(01:01:30):
went out there and sat in that chair and I
was looking up at it was beautiful, and I was,
you know, rock up right on the beach, and I
was looking up at the sky and there was a
million stars in the sky. And I had to drink
betray my legs and I fell asleep and I woke
up the next morning with the sun coming right over
the hill, and I was covered in mosquito bites. And

(01:01:51):
that day I started writing down the lyrics Stow Blue
Chair and finished it several months later.

Speaker 2 (01:01:57):
But that'd be I mean, as a songwriter, that would.

Speaker 1 (01:01:59):
Be number one number two.

Speaker 3 (01:02:00):
Number two would as a songwriter slash artist would be
I go back. Uh. Number three would probably probably be
there goes my life. Number four would probably be.

Speaker 2 (01:02:15):
Anything but mine.

Speaker 3 (01:02:18):
And then I don't know, there's like young summertime.

Speaker 1 (01:02:22):
When you said you went Tequila's top five. I met
te keilast to be five. But if I had it
could do another five. It would be young, it would
be summertime. It wouldn't be saving for any day. It
would be I don't know. Uh uh, you know, the
duet with Pink was a lot of fun. I'm not
forcing to do a top other five.

Speaker 3 (01:02:42):
Yeah, okay, some alternates we could put that in there.

Speaker 1 (01:02:46):
Yeah. I really enjoyed this. We were talking about before
you got here, this fear too. So those after you
do it the first time, I guess people have seen it,
they want to come back. Do you do you feel
like you need a promo as much now? Do you
just feel like it's gonna sell like crazy because the
proof of concepts already there?

Speaker 3 (01:03:03):
Well, I mean you got a promo promo for sure,
but it's just such a unique experience.

Speaker 1 (01:03:09):
I'm coming to this one. I'm coming to this one.

Speaker 2 (01:03:11):
Yeah, please come.

Speaker 1 (01:03:12):
I just saw so many of my friends going like
they were like, we're with like coaches that I know,
Like I saw like Dan maull and I got the
all these guys that are like.

Speaker 2 (01:03:18):
My Dan mull and I believe was at every show
he let us.

Speaker 1 (01:03:24):
By the way, Dan mullin for those who don't know
right now, he's the UNLV head coach, but he was
at Florida, he was a television.

Speaker 3 (01:03:30):
A Mississippi State, and he was you know a lot
of places, and he got a he got the gig
at UNLV, so uh he let he let me and
Bailey come.

Speaker 2 (01:03:38):
Work out that we were.

Speaker 3 (01:03:39):
I worked out at UNLV's football facility every single day
for a month and a half that I was in Vegas.
So I would go into that backstage area, you know,
I had a little area we called the sock Monkey Lounge,
and I'd go in there and say how to people,
you know, and nine times out of ten I'd see
Dan there, you know, Like.

Speaker 1 (01:03:58):
That was the trade off. That's awesome.

Speaker 3 (01:04:01):
I love it.

Speaker 1 (01:04:01):
I'm a big fan. I've often said many times because
I'm from Arkansas, we didn't have beaches, ye, so to me,
I'm not drawn to beach. I love Emo Kenny.

Speaker 3 (01:04:09):
Yeah.

Speaker 1 (01:04:10):
Beach Kenny's got some bangers, yeah, but I love Emo Kenny.

Speaker 3 (01:04:14):
Yes. That's what's interesting though, is like it's not necessarily
a beach thing. It's more of an island culture.

Speaker 1 (01:04:19):
Yeah. I don't have that culture either, and so I
get annoyed they don't bring food quicker.

Speaker 3 (01:04:22):
So there's the Emo in that too, though. I mean
there's a lot of singer songwriter in me that came
from that.

Speaker 1 (01:04:27):
I'm sure it's a huge influence. I spent five.

Speaker 3 (01:04:29):
Years like well, I would get off the road and
there was there was a huge part of about five
or six year period of my life where I truly
I would pack to go home.

Speaker 2 (01:04:40):
I was gone so much.

Speaker 3 (01:04:41):
So what that means is I would get off the
bus and I wouldn't come to Nashville. I would go
to my boat in the Virgin Islands, and so I
over a period of about five years, I wrote a
lot of different songs that didn't necessarily fit on your
you know anywhere else in your life that you're building,
which which ended up being some of my favorite records.

Speaker 1 (01:05:01):
You ever get stung by starfish or a jellyfish? I
guess starfish don't sting. Yes, jellyfish douce I got stung, yeah,
a couple of times. Shark encounter with a shark. No.

Speaker 3 (01:05:11):
I went diving a lot with my friend Bob Schenners
into Virgin Islands and I saw a bunch of sharks.

Speaker 1 (01:05:15):
No risk, no death. No.

Speaker 3 (01:05:17):
I mean like if they when they know you're not food,
you know you're pretty safe, all right, That's what happens though,
Like if they think you're food and they don't, you know. Yeah.

Speaker 1 (01:05:26):
So I really appreciate you coming by, really because this
is our first man first, I'm gonna be the first one,
number one. You know, we've we've we have some others
in the can. We got to go a one with Kenny.

Speaker 3 (01:05:38):
I'm really appreciative, first round draft shake you man, and
for everything, and it's it's good to be your.

Speaker 1 (01:05:43):
Well, I appreciate it. There is Kenny Chesney thinks come
to fear Bobby. Yeah, I said I would last time.
This time though I'm only partially lying. All right, there
is the great Kenny Chesney. Thanks for listening to a
Bobby Cast production