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November 16, 2025 20 mins
Heart Life Music is a love letter to the journey: all the places I've gone and how we got here. This book takes you on the ride.Knoxville. Moscow. Myrtle Beach. The Virgin Islands. Plentywood, Montana. Holmdel, New Jersey. Key West. New England. The Road. No Shoes Nation. Beyond.We've had a lot of fun, a bunch of challenges, a few moments of wondering "what the hell?"-and more love than any artist deserves. You're gonna meet so many people, some you'd never expect to see crossing my path, whether it's the Wailers, Willie Nelson, John Madden, or Grace Potter. Maybe you won't be surprised at all. I just know this: A whole lot has happened.For anyone who's found a piece of your life in any of my songs, this is for you. Open a cold drink, get out on your deck or your boat or wherever your happy space is, jump in, and live them along with me.And if you've got dreams, whatever they are, know they don't always come easy. But if you believe, do the hard work, and keep coming back, you'd be amazed at what can happen. I'm a pretty average guy, so look at this-know you might could do it, too.It's been a helluva trip around the sun.

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
It's just one of those things that I do. I
host seventeen different podcasts, so the question is where are they?
How can I find them on these digital platforms. Well
it's very easy now ero dot net, a R r
oe dot net. Thank you so much for all your support, Holly,
You've done an amazing job here in the way that
you know that Kenny Chesney has been the ultimate performer
for so many different people who love their genres. Whether

(00:22):
you're a country music fan, whether you're somebody who just
likes some good yacht rock, island rock, whatever. Kenny Chesney
seems to be that guy that stepped into that role
and continues to be that connection to everybody and not
just a genre.

Speaker 2 (00:36):
I think, Yeah, it's funny because you know, Sammy Hagar
is one of his best friends, and if you want
to talk about rocking out, Steve Miller, Eddie Van Halen,
Chras Potter, even Cracker to an extent, it's it's a

(00:56):
funny thing. When he was a kid in a really
tiny town outside Knoxville with no light pollution, which is
why the book starts looking up at the stars, because
that's what there was. He really only got what you
could get on the radio. It didn't all live in
the palm of your hand. So his journey was very

(01:18):
much Alabama and George Jones and Merle Haggard in bluegrass.
Then when he got old enough to start playing football
and going and hanging out with his friends, he got
all the Southern rock from the older kids right down
the block Lennard Skinnerd. If you haven't read the book,
there's an amazing scene where he's kind of at the

(01:41):
end of his tether it's not working and Skinnerd shows
up right. I mean, what a magic moment. And you
know he loved all of it. So once he started
finding Van Halen and this Steve Miller band, he literally says,
I go back in the joker is an entire summer

(02:02):
he spent as a lifeguard in high school. Wow, right,
and he lives in the music. So for him, once
he got to that place where he had a triple platinum,
Greatest Hits and he was successful, but he knew that
he wasn't truly himself. He started looking around and thinking
about all of his friends in the Islands who were

(02:25):
not anywhere near the music business, and how they were
able to love George Jones and Bruce Springsteen and the Whalers,
And that's when really his career took off, right when
young happened, which is those melodic van Halen guitars, that

(02:46):
big John Mellencamp, you know, the kick drum that hits
you in the chest and the handcliffs, and he just
it just he was off and lived those songs again,
which I always think he kind of cut for the
homeless veterans down on Lower broad when it was pretty
much just a dissolute place for homeless stars who never happened,

(03:13):
hookers and tourists that didn't understand the rhymen was about
to be torn down right. The guys and that guy
and live those songs again could have been one of
the people he was playing for when he was a
kid fresh out of college.

Speaker 1 (03:28):
To be able to sit down with him and look
him in the eye, because all we get are the
videos on YouTube, and we may get some click stuff
on TikTok and stuff like that. But to hear these
stories and then to sit back after you now are
holding the stories, I can't imagine what's going through you.
As a historian of music.

Speaker 2 (03:47):
Well, you understand, I've been here since two thousand and one,
right right. I've been a music critic since my sophomore
year in college at the University of Miami. I started
writing for the Miami Herald and was on the road
with Neil Young at twenty. So I've been part of

(04:07):
Kenny's journey for twenty five years. And the three things
that go through my life since I believe you really
want to know, I'm so proud for him, Yes, because
I saw how much, to quote almost famous here, they
don't know what it means to be a fan love
some band or some silly little piece of music so

(04:29):
much it hurts. Kenny knows how that feels. And i
know because I feel the same way. And I'm proud
to watch somebody who always made it music first. Right
when he cuts those songs, he wants to know that
it's goodna say something to the person who loves his
music that they might need to hear. And he would

(04:51):
tell you when he realized he wanted to communicate truth
about his actual life and not just songs that were
working in the format, That's when it started to really
connect for him, Big Star. How many girls did he
knew that wanted that dream? Right? And it wasn't just
about I'm pretty They burned with the same passion for songs.

(05:15):
He tells this story about a waitress at Brown's Diner
named Amy Mayo who went on to be either the
b m I or ASCAP songwriter or the year right,
like that's big star as much as Taylor or Megan
Maroney or Grace Potter. And the second thing I feel

(05:35):
is it was a thrill ride. I was there for
a lot of it. I was there when he walked
over to the Four Seasons to meet Jimmy Buffett for
the first time. Wow. I was there. My assistant's like,
you got to get down at the studio and Kenny
was doing some demos and I'm like, no, I've got it,
blah blah, and she says, no, you need to go now.

(05:57):
I'm like, okay, Amy, And he had the faed X
from Bruce's studio. Like when I saw the return address,
I looked at him and it was Bruce having fed
ex to him a note after Kenny sent him one
step up to talk about how much his cover meant

(06:17):
to him. And we were like two kids going in
the parking lot because you know, I had said you
probably ought to send him this and be a man
and own your work because you really care about this song.
And Kenny's version of one Step Up is as good
as Annie Springsteen cover Out There, I think. And I'm

(06:37):
a kid from Cleveland, Ohio, so you know I mean,
I'm I'm old enough. I exist long before born in
the USA. I bought Darkness on the Edge of Town.
I was so young I didn't understand it. But when
that hit the record store, I was going to vote

(06:58):
with my money. So that's thrilling. And you get to
have all these moments. You get to see Sammy Hagar
when Kenny walks through Customs and Cabo for his birthday party,
standing there with a mariachi band and two trays of
margaritas for him and the band Holly.

Speaker 1 (07:16):
People of music need people like you, and we need
more stories from people like yourself, because that's the thing
about it is that you know, unless you've been in
that green room, or you've been on that bus, or
you've been with them while they're writing songs, the average
listener does not know of the personal journeys that creative
people go through. And when you write about Kenny's soul
searching and stuff, all I did. I put the book

(07:37):
down and I just go, just let me feel this.
I'm here because I'm supposed to learn something. And then
to hear how close you are, it's like you were
in those moments to where you had to have closed
your eyes as well and said just feel from it.
Just feel feel, feel, feel, feel feel absolutely.

Speaker 2 (07:52):
I mean Cameron Crowe, who's got the un cool out
right now, who is the man almost famous, was kind
of love lot of his childhood. He would say, I
was the next one, right. I was a baby rock critic.
I was super young. I looked even younger. And I
think kids like us, we want to know where the

(08:14):
music comes from, want to understand why it makes us
feel what it feels, and we respect the process of it.
Like I don't care what kind of exfoliant you use
or when your kid lost their first tooth unless you
wrote a song about it, right, Because to me, that's

(08:34):
just cheap marketing for people that don't care about music.
But when you're a true believer, and I am, it's
those things where you have the dark knight of the soul,
or you sit on the bow of your boat and
you hear Grace Potter saying apologies and your whole soul

(08:55):
gets torn wide open right. That to me is what
makes you and Tequila so profound. Yeah, those are two
people that meet and see each other in a way
that has nothing to do with what the stylists put
them in or the Wracker company thought would be a
great way to maximize two non overlapping audience segments.

Speaker 1 (09:18):
Please do not move. We'll be back with Holly Gleeson,
coming him next the name of the book Heart Life Music.
We are back with Holly Gleeson. One of the things
that's always been inspiring about Kenny Chesney is that once again,
that door has always been opened for all people of
all music to step in and so to you know,
to pick up on a Grace Potter song with Kenny Chesney.

(09:39):
The average person that does not know of Kenny Chesney
sits there and thinks that Grace is part of the band.
And that's what I've always loved about Kenny Chesney. It
doesn't matter who he's singing with. You're part of the band.
You're part of the moment. And if you walk away
saying okay, he's part of the band, he did his
job right. Because there was not two different people. It
wasn't a Paul McCartney, Michael Jackson. The girl is mind
situation here it works together.

Speaker 2 (10:02):
No, he has been talking a lot on the book tour,
in the book events. There was absolutely zero marketing when
he pulled a collaborator in it's because it is his
heart life music, Uncle Cracker. I remember I was in

(10:22):
the studio when they caught when the Sun went down
and like two people that probably shouldn't be in the
same room, all the gold teeth in the bag of crystals,
but white Castle, sorry, got to get the brand right.
But they had the same euphoric young man's heart, like
they just love the joy of it. And when you

(10:45):
put them together at worked. When the whalers had these
songs that hadn't been completed and they reached out to
people to finish the songs. Family man called Kenny because
they'd done the video for Everybody Wants to Go to
Heaven and the CMA Awards and Tootsies the legendary bar

(11:07):
on Lower Broadway, and they saw someone they felt kinship with.
You know, when Kenny made that video, he wanted to
sit on the North Bank of Jamaica and hear the stories,
not tell them what a big deal he was. And
you know, that's always been kind of the litmus test.
He and Dave Matthews were always in the top three

(11:29):
ticket sellers in the two thousand and zero at an integer,
and people didn't know they knew each other, and they
kind of did because they were on the same roads.
But I'm Alive was a song that both of them
organically had lived. The exhaustion of what it takes to
do this, but the gratitude for what you get to

(11:51):
give people when you got on that stage and you
share your music. Wow. Wow.

Speaker 1 (11:56):
My mother was so in love with Kenny Chesney, and
the reason why is because because she felt like that
the way that he loved to hide his eyes that
she used to tell me all the time. She would go, Sun,
you need to sit down and hear what he's saying.
Do not try to read what he's singing through his eyes.
Do you believe in that theory?

Speaker 2 (12:16):
Kind of? I think I think your mom's onto something.
I also think there's a part of him that's a
little bit shy. Yeah, believe it or not. Like he says,
I can rock sixty thousand people, no problem, talk to
six I want to get under the table yep. And
when we're out doing the book evouents, it's been really
funny because he says the same thing every night. You

(12:37):
have to really love somebody to want to listen to
them talk.

Speaker 1 (12:42):
So then how does he deal though with post production blues?
Because those of us that are in the creative business,
we understand that when you step off that stage of
sixty thousand people and now it's a series of maybe
two or three, or you go back to that hotel
room alone, that's it. Post production blues has its free
ticket to get into your heart.

Speaker 2 (12:59):
Absolutely. I think there are a couple of things, and
it's in the book for sure. You know when he
has the first headlining show in West Palm Beach and
you know everything of the Goog, the goodbyes have been said,
the pictures have been taken, and he's alone in the
stateroom with just the sound of the diesel engine. Right,
you have that moment of reckoning and that particular night

(13:23):
he wrote a contract with his soul. He saw what
was possible for the first time with this special blend
of rock and country and island music, and he said,
I'm gonna literally every spac sell Adam whisper of who

(13:43):
I Am, I am going to give to this music,
and he did, and you know, the jumping forward. The
next really big rackoning is two thousand and nine in
Indiana when he's headlining the I don't know the name
of the field now because they're different, but he played

(14:03):
the NFL Stadium in Indianapolis and there's nothing left to give,
like he is literally run out of specs, atoms and
whispers and he crashes and burns right, And there's that
video on YouTube. You know, Kenny Chosney cryes on stage.
That's all very real. And the reason he's crying is

(14:25):
he didn't know what else he had that he could
give them, and his music very much is his heart.
Here you go take it, take it all and use
it to feel better, Use it to find your joy,
use it to find your strength. And one of the

(14:46):
things I think that's come out of the book is
use it to find your own courage to chase your
dream and to face all the places where it's hard
or you're frustrated or cause you know, if you've read
the book, you know, Oh, there's this scene in the
kitchen whereas mom says, you know, baby, if you want
to come home, that's it. And I mean, like I've

(15:08):
got tingles because I called her after we wrote it
and I said, can I read you this? And she
got very very quiet, and she said, and she's the
greatest I think. You know, his his outboard motor is
his mom, because she's everything he has on steroids. She said, yeah, baby,
that's that's just how it happened. H So, you know,

(15:34):
there's a lot of real in this book, but there's
also a lot of and then you're going to find
that spark and you're going to keep going and look
at all the amazing fun you can have if you do.

Speaker 1 (15:45):
Holly, you know, this book is a dear future reader
moment that somebody five, ten, twenty five years from now
is going to pick this up and because you took
the time to really put it into a book form,
they've got something. And because we're not all going to
be addicted to chat, GPT and Google forever, we have
to have real, authentic stories just like this.

Speaker 2 (16:05):
I think it's funny to say that one of the
things that was a big driver for him was he
believes there kids out there that want to write real
songs life be're in Mexico. People think it's a party song,
and the truth is it was him wrestling with all
the expectations of you're thirty six years old, why haven't

(16:27):
you settled down, Why don't you have a house, a wife,
kid's a picket fence, And there was a lot of
pressure I think in certain parts of his world. Certainly
not for me because I'm the spinster who's been engaged
six times. But you know, in that moment, he realized,
rather than worry about having all the answers, why don't

(16:49):
you be in the moment, appreciate where you are, take
it for what it is, and be grateful and have
the fun if that's what there is. They'd played almost
four hours at Cabo Wabbo for Sammy's birthday, and Sammy'd
gotten up and sung were dumb like Anthony gotten up
and played with them, and it was it was a

(17:09):
very big watershed moment. People think it's a party song,
and it's not. It's about being good with who you are,
where you are, And for the kid that doesn't want
the algorithm to tell them what to sing but wants
to write their life. Kenny would point to that song
and say, right there, and for somebody that doesn't want

(17:31):
to be a social media moment, right, Like we've always
had them Achy Breaky Heart, Billy Ray Cyrus who was
a bigger star, right, But that was a moment that
they never built into something more meaningful. And Kenny's thing
was always and he talks about this being a roadmap

(17:52):
to your crazy dream. Here's how you chase it, here's
how you build it. He wanted to know that everybody
who believed and wanted to come along, not only was
there a place for them, but we weren't going to
break down on the side of the road and you'd
be looking around going Now what.

Speaker 1 (18:12):
You're very clear in the very beginning part of this
book this is not a memoir. And in listening to
you and in reading the book, the one thing that
I've learned it this is a book about growing forward.
It's about Okay, okay, so we did this, So what
let's see what we can do now. Look for book
two to come in the years ahead. I mean, you're
all about putt you know, that forward motion kind of movement.

Speaker 2 (18:31):
Yep, both of us. Yeah, Because you know, it's so
easy to stand in a moment like, oh look what
I did. But the truth is, if that's all you got,
you know what a sad life you've peaked. Steve Girl
has that amazing song number twenty nine about the kid
who's a high school football got and then it's over,

(18:54):
And I think most human beings they forget that there's
another dream. Go get it whatever it is. If your
dream is just you want to teach three little blonde
headed kids how to fish, that's a great dream. Like
I'm not telling you everybody's got to go sell out
football stadiums, But it's always better to have something to

(19:18):
reach for, and it's always better to have that next amazing,
awesome thing out there because there's a lot of joy
in building. You can take a lot of people along.
His three best friends from high school and college, they're
out there. They're a big part of the touring machine
thirty two years later. And when you can do it

(19:40):
with your friends, when you can make space for people
you love to go on the ride with you, what's better.

Speaker 1 (19:46):
Wow, you got to come back to this show anytime
in the future. Twenty minutes with you talking about Kenny Chesney,
that's not enough time.

Speaker 2 (19:53):
You got to come back, Well, anytime you want me arrow.
You know how to find me, you bet I do.

Speaker 1 (19:58):
You'd be brilliant today, Okay,
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