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August 14, 2024 30 mins

When OutKast dropped “Ms. Jackson” in the fall of 2000, the world was stunned. Nobody had ever heard a hip-hop song that sounded anything like this. But there’s never been anybody like OutKast before. On this week’s episode, hosts Rob Sheffield and Brittany Spanos discuss “Ms. Jackson,” and how it fits into the long illustrious OutKast story. They’re joined by their brilliant Rolling Stone colleague Simon Vozick-Levinson as they break down this song, its timeless appeal and the mighty legacy of OutKast.

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Speaker 1 (00:00):
Welcome to five hundred Greatest Songs, a podcast based on
Rolling Stones hugely popular, influential and sometimes controversialist.

Speaker 2 (00:07):
I'm Britney Spanos.

Speaker 3 (00:08):
And I'm Rob Sheffield and we're here to shed light
on the greatest songs ever made and discover what makes
them so great. This week we're talking about a gray
one m Miss Jackson by Outcast.

Speaker 4 (00:20):
Yeah.

Speaker 1 (00:21):
This is one of four Outcast songs that made the list.
Miss Jackson is at number one forty five, and then
we have hey Ya in the top ten at number ten,
Bob Bombs over Bagdad at number thirty nine, and of
course their UGK collaboration International Player's Anthem is at number
ninety one.

Speaker 2 (00:38):
I love Miss Jackson.

Speaker 1 (00:39):
I think is probably the first Outcast song I'd ever heard,
but it's I'm so excited to talk about today.

Speaker 3 (00:46):
That's so amazing. It's such a beautiful song.

Speaker 1 (00:48):
Yeah, and this was on their two thousand albums Sanconia,
and it was the second single after Bob and Bob
was ended up being you know, sort of kind of
not the biggest hit to debut from the album. It
was also banned from rap radio and it just you know,
it wasn't wasn't really like the launching point that their
label intended probably for the album, but of course Miss

(01:10):
Jackson ended up becoming this like massive breakout hit for
Outcast and just like a giant moment for them.

Speaker 3 (01:17):
Absolutely really the opposite of Moms for Baghdad, just in
terms of the sound and approach.

Speaker 1 (01:22):
And this was a song that ended up hitting number
one and it was It won the Grammy for Best
Rap Performance by a Duo or a Group. And it's
also a very personal song for the band. This is
about Andrea's relationship with Eric Abadou, which it had ended
prior to the album being released, which I kind of
loved this like little homage to his relationship with her
and her mom.

Speaker 3 (01:42):
Yeah, very unusual to have a song to her mom
at all.

Speaker 2 (01:46):
Yeah.

Speaker 1 (01:47):
Yeah, and very kind of like great sort of dedication
to you know, the idea of breaking someone's daughter's heart
and kind of like how you deal with that, and
this like apology to both of them at the same time,
and it just comes out so well.

Speaker 3 (02:02):
This song is just very different from anything anybody was
doing at the time.

Speaker 1 (02:06):
Yeah, and even for Outcasts it ended up being you know,
this was kind of a moment for both of them
where they were sort of shifting their sound a little bit.
I think even for Andrea specifically, like this was kind
of the beginning of him doing more search like melodic singing,
sing rapping instead of just like straightforward rapping on every
Outcast song. Of course, we would see a lot more

(02:28):
kind of of that sort of diversity of his own
performance style on speaker Box, Love Below and Idlewild, but
this was sort of that beginning for him of like
really honing in on that.

Speaker 3 (02:38):
Something like Bombs over Baghdad. I mean, it was so
avant garde, it was so challenging, it was so hard,
Miss Jackson. It just comes straight from the heart. Yeah,
very personal story, very unusual kind of thing for to
be singing about real life relationship that way.

Speaker 1 (02:54):
Yeah, and Andrea talked about how the song kind of
started out as this acoustic guitar song and ended up
switching it because he felt like it was just not
really what Outcast was doing or kind of what people
would want to hear from them, So ended up switching
the song. And they have this like really great sample
of the Brothers Johnson's version of Strawberry Letter twenty three
and kind of have this like cool sort of like

(03:16):
reverse flip of the of the sample and the song
on it, which is like that kind of I you know,
like reverse kind of flip under it. I've always really
really loved the way that sounded under under the vocals.

Speaker 3 (03:27):
Yeah, a familiar seventies sound with very outcast twist on it.

Speaker 2 (03:32):
Yeah.

Speaker 1 (03:33):
Eric has talked a little bit about the song and
about sort of like her own reaction to it, and
I really love that. She kind of talked about how
it was sort of like a sore spot for her
at first, just because especially with Big Boys verse, she
kind of liked that part was sort of it was
a little tougher because they had broken up. They you know,
heard Andre Shrison that they had had over the course
of their relationship, and she said it hit kind of

(03:55):
a sore spot. I didn't want to hear that, especially
when I heard Big Boys verse. When I heard Andre's verse,
I felt very good because his verse was really really inspiring.
He just said how he felt and it was his
honest feelings, and I always respected that and listened to
what he felt and appreciated it. And she said that
In twenty sixteen, I talked about how her mom Loves
a song and like a Miss Jackson license played and

(04:15):
you know, a mug and an ink pen and just
kind of course embraced kind of being the titular Miss
Jackson in the song.

Speaker 3 (04:22):
Absolutely, and Eric's legend had really grown so much over
the past few years. It was wild that you could
hear the song as most people did, not knowing who
it was about a specific person, but for somebody as
legendary as Erica, it was just really enhanced knowing her
work and how powerful that is.

Speaker 1 (04:41):
Yeah, what do you remember of like hearing Outcasts for
the first time or kind of hearing kind of this
band that was just like such like an explosive moment
in hip hop and in pop music when they kind
of came on the scene and started to blow up.

Speaker 3 (04:54):
Yeah, hearing Outcasts for the first time was a total transformation.
It was the Equimini era. Yeah, I was watching MTV.
I saw the video for Rows of Parks and that
was the first time I ever heard of Outcast and
Rose of Parks completely blew my mind.

Speaker 2 (05:10):
Yeah, all the.

Speaker 3 (05:11):
Innovation in that song, all the humor in that song,
all the brilliance in that song. And I went out
and got in the car and drove to the mall.
It was right before closing time so I could buy
that CD. So I took it home and just listened
to a Quemini all night.

Speaker 1 (05:26):
Yeah, I think I think it was like Miss Jackson
was the first one that I'd heard, especially because that
video was such like a heavy rotation and TV video
of course, you know, with all the kind of animals
bobbing their heads and just sort of, you know, ingrained
in my own kind of consciousness type of video. But
obviously you know speaker Box Love below coming out when
it did, and sort of being in middle school and

(05:46):
all those songs, Like, I mean, Outcast ended up becoming
just like one of the most important and biggest acts
of that time for I think a lot of people
listening to pop music to rap music at that time.

Speaker 3 (05:56):
It was so huge and so innovative. That was absolutely incredible,
their band doing things on every level that was unpredictable. Nonetheless,
it's so much pop appeal.

Speaker 1 (06:08):
Yeah, I mean, even coming after Ms Jackson and Bombs
of Her Baghdad and Rosa Parks like was kind of
the later music that Outcast released. Was that like a
very big shock or was it something where you were
just kind of like anticipating to be shocked by whatever
outcast was.

Speaker 3 (06:23):
Yeah, I mean the way they would evolve from album
to album and after a Qumini a Qumini was just
so mind blowing, and it seemed like both of their personalities,
their artistic personalities were so pronounced at that point, and
their originality was so pronounced at that point. And then
hearing them move on to Stanconia, which is such a
diverse album, such a radical album in so many ways. Yeah,

(06:45):
and as so many different kinds of songs on it,
Miss Jackson really stood out though.

Speaker 1 (06:49):
Yeah, I feel like the first time I'd listened to
a full album ended up being Speakerbox Love Below, and
like then going back and listening to their previous albums
just feeling like not really knowing what to anticipate, you know,
everything they're doing, and like everything they had been already
sort of establishing as their career and as their their sound,
Like it was just so many things at once and
still felt like so uniquely outcasts in the way that

(07:10):
they expressed themselves their own flows, like they had such
distinct identities both Big Boy and Andre as their own
performers and it just kind of always translated really well
over no matter what genre they would do or kind
of what sound they would want to like evoke in
their songs.

Speaker 3 (07:26):
Yeah, they could do any genre, and that there were
pop songs that were mostly andre inflected and then Big
Boys more hardcore sound that was there, and their sound
from the beginning, Andre had that really pronounced poetic streak, Yeah,
and that was there on Quemini. That was there, going
back to the earlier stuff, but it was really incredible

(07:47):
how they would evolve album to album and they would
get more extreme, big Boy would get more Big Boy,
Andrea would get more andre Intel. An album like speaker
Box Love Blow is really split between their personalities in
a way that Quemini already was. The Quemini is their
astro signs the Aquarius and the Gemini Speaker Box Love below,

(08:07):
it's gotten so extreme how different their approaches are.

Speaker 1 (08:12):
I always just really really love that the way they
play off each other, with andre Bean sort of this
like lover boy and like almost kind of coming off
this like very sort of not not always but typically
pretty romantic sort of view of the world, and kind
of the way that even just on mis Jackson of course,
just like his sort of dedication and like this like
tenderness that he has towards his partner and his partner's mother,

(08:33):
and then Big Boy kind of being much more of
the player, like a little bit of like, you know,
just a little bit of the fuck boy character and
opposition to Andrea.

Speaker 2 (08:42):
I always love the way they played against that.

Speaker 3 (08:44):
Well, and in such a personal song. For Andre to
drop that verse, it was wild how Big Boy gets
so pronounced in his personality in this song drop it
into his song. That's very personal for Andre.

Speaker 1 (08:55):
Yeah, and you had mentioned earlier the idea that people
didn't really know about it, being like Erica a bad
inspiration kind of what was the level of like, like,
who were Andre and Erica? I guess as a couple.
Were they very public or were they kind of like
I feel like there's so much of that lore and
people sort of like having this romanticized kind of version

(09:15):
of this couple that existed twenty years ago. But at
the time, did people know a lot about their relationship?
Were they very private?

Speaker 2 (09:22):
What was that? Like?

Speaker 3 (09:23):
They were very private? Andre and Erica both had their
own legends, and Erica was so such a poet, she
was so inflected with that progressive R and B that
she perfected in the nineties, so her legend was already secure.
It didn't overlap that much with the kind of stuff
that Outcast was doing. And definitely it was more Andre

(09:45):
than Big Boy, Yeah, that sort of soul aquarian perspective.
But Erica was an artist who evolved album to album
as well.

Speaker 2 (09:53):
Yeah.

Speaker 1 (09:53):
I mean it's been so like fun to kind of
see over the years, especially they went on hiatus in
two thousand and seven, and they unity in twenty fourteen
for a string of festival dates, which was great to
kind of catch them at that point and be able
to finally see them live.

Speaker 2 (10:07):
But you know, they've.

Speaker 1 (10:08):
Had such appropriately divergent career of hats since two thousand
and seven.

Speaker 2 (10:14):
Of course, most recently, Andrea.

Speaker 1 (10:16):
Released an album that's entirely flute compositions, which is I
don't know if anyone s could have expected anything else
from Andre right now.

Speaker 3 (10:24):
It's so hardcore. I love that, And with people waiting
so long for new music from Andrea, yeah, and it
turns out to be the flute, and people listened to
the flute.

Speaker 1 (10:33):
Yeah, I have I know a lot of people who
went that he just did a concert and that was
kind of a big pilgrimage for a lot of people
to go to the show and just see Andre play
the flute. Big Boy, of course, has released several solo albums.
He's done a lot of collaborations and production work with
other people, and he's very instrumental in Ghannamne's career and
you know, working with a lot of younger artists. And
also has his owls that you know, I'm a very

(10:54):
big fan of Big Boys three owls that he has
at the Stanconia Recording Studio and and Ben building. But
he has three great owls that I'm obsessed with that
he posts a lot about on Instagram and allegedly worked
at a song with Kate Bush as yet to be released,
but that he talked about a few years ago that
I'm very much looking forward to.

Speaker 3 (11:13):
I cannot wait for that collaboration and the way their
sensibilities overlapped. But it's about their careers since then have
gotten so different. They've gone to opposite extremes. But the owls, well,
the flute is kind of the owls.

Speaker 2 (11:26):
Yeah.

Speaker 1 (11:26):
Instruments, Yeah, I think that it definitely makes sense, Like
you know, that's kind of the unifying part of Outcast
right is like a little bit of the flute owl
kind of dynamic that they have.

Speaker 3 (11:36):
Yeah, for artists like them to have their own careers
after being together for so long, but there's still those
sort of there's still those personalities that they were in Aquimina.

Speaker 2 (11:47):
Yeah.

Speaker 1 (11:47):
Do you have a favorite track or several tracks.

Speaker 3 (11:51):
By Outcast well Rosa Parks, Yeah, kind of goes back.
That's the shock of the new Yeah, bombs over bag
Dad was bigger for me personally than Miss but Miss
Jackson is equally radical. Yeah, they're both Bob and Miss
Jackson are both really radical songs and that they're unlike
anything else that was going on at the time.

Speaker 1 (12:10):
Yeah, Yeah, mine is Roses. I'm a big speaker Box
Love Below fan. That album was I think released at
the exact right time for me, where it was like
hay On Roses were like the first two songs I'd
ever bought on iTunes, you know, this was like finally
had like my own way of buying music, and it
was that song I always really loved just kind of
how the drama of it, the weirdness of it, the

(12:32):
theatricality of that in the video, like before I entered
my full theater kid era. I feel like that was
a good precursor to what was going to come for
me in a few years.

Speaker 3 (12:42):
That's an amazing song. It was just very funny to
hear on the radio. Sometimes you know, the word poopoo
would get ansored and sometimes it wouldn't.

Speaker 1 (12:51):
I think it was also probably the eleven year old
tensive humor of hearing out Cass poopoo on the radio and.

Speaker 3 (12:57):
Definitely the first time it had been done hit that.

Speaker 2 (13:00):
Mass hit and who else could have a hit other
than a Cast with that?

Speaker 3 (13:03):
No, but it kind of it typifies their originality and
as you said, the theatricality is so important in that song.

Speaker 1 (13:10):
Yeah, And I mean, what is it about like Outcast,
especially this era of Outcast that has had such an
impact on music or pop culture in your mind, Like,
what kind of is that legacy of miss Jackson and
this particular moment for Outcast.

Speaker 3 (13:23):
For such a personal hip hop song, and it's at
a time when it was very different from the kind
of song that it was autobiographical. But like you said,
there's a lot of tenderness in the song, the emotions
that he expresses are very introspective and very delicate. Ye,
He's talking about personal weaknesses, personal failures. He's talking about
a relationship that, as we were saying, was very private

(13:46):
at the time, and talking about the end of it
but also facing the responsibilities that came with it. So
it's about their past, it's about their future, but that
it's such a personal song just really different.

Speaker 1 (13:57):
Yeah, I mean, even just in the way that the
Beak kind of does that sort of rewind kind of
record scratch thing, Like there is so much of that
kind of like evoking of that nostalgia for relationship, that sadness,
that kind of like just general kind of energy that
especially Andre is bringing to that story about you know,
of him and Erica and this relationship with her and
her mom. But yeah, I mean, I think, you know,

(14:17):
just again them sort of playing with these two different
sides of like how to approach a very like delicate
type of relationship with.

Speaker 2 (14:24):
Your partner's parent is very kind.

Speaker 1 (14:26):
Of that unique outcast humor and kind of weirdness that
they bring to everything.

Speaker 3 (14:31):
Yeah, there are not enough songs about dealing with the
partner's parent. Yeah, and it's a topic that had not
been explored on this level. Definitely not in the song
this great. Yeah, but for him to get so introspective
and confessional about real life and that real relationship at
that time was really it was really innovative for him.

Speaker 2 (14:54):
Yeah.

Speaker 3 (14:55):
Outcast breaking up was not a surprise. Yeah, everybody knew
it was come. And they've been drifting apart artistically really,
even Speaker Box Love Below, where it's basically two separate albums. Yeah,
but even on Stanconia and even in Miss Jackson, that
divide is.

Speaker 1 (15:11):
There, Yeah, definitely it. You know, there is so much
of them really wanting to establish who they are as
artists and be bigger than just the group, which is
you know, it can be such a trap for anyone
to be in a duo or in any type of group,
and so it's very clear that they want to establish
early on that they have individual identities that are outside

(15:33):
of Outcast and that at some point they will be
exploring those identities because they are such disparate artists, you know,
there is so much of that chemistry that they have
is because they're so different, and that makes it work
so well, is that they have you know, there are
a lot of things that bond them musically, and you know,
kind of creatively, but their personality is their own delivery,

(15:53):
is the own way that they approach things is very
clearly different from the beginning. And again that's that's a
lot of the appeal of how Cast works is that
they find this like really miraculous and cool way of
making that feel so seamless and kind of play off
of each other in a really fun way.

Speaker 3 (16:09):
Yeah, they coexisted for so long. Did you see their
amazing Saturday Night Live performance around the time that Stankonia
came out.

Speaker 2 (16:17):
No, I don't think I did.

Speaker 3 (16:18):
They did an absolutely iconic Saturday Night Live and it
was bombs over Baghdad and it was seeing them bring
that sort of that flare to the presentation of it
just as a live presentation, Yeah, it was something totally different.
It was definitely one of the most iconic Saturday Night
Live appearances ever. The song sounded like nothing that anybody

(16:41):
had ever heard, but just as a live thing, it
was such a full show. There were so many people
who are making it a full on presentation. Yea, it
seems like a very different song to do live.

Speaker 1 (16:50):
Yeah, And also, like while we've been talking, I've been
thinking about other sort of especially with this season of
the podcast, and like other episodes we've talked, I feel
like we've talked about we've brought up Outcast a lot,
and I feel like, even for the artists that we
both kind of like talk about a lot, like, I
feel like Outcast has come up a bunch, like and
the you know, when we talked about Kate Bush, when
we talked about Beyonce, and we talked about of course
the International Player's Anthem, where we had like the other

(17:12):
another Outcast song, Like, I feel like they've ended up
sort of organically coming up a lot, And it's so
fascinating how much Outcast feels like kind of like the
center of the of the pop universe in a lot
of ways. And it feels like there there's such a
long sort of tale to their musical legacy and to

(17:32):
their musical influence. But I also cannot think of a
single act that sounds like Outcasts since since.

Speaker 3 (17:39):
Them absolutely very different dynamic for a duo, and even
though they've been so influential, you do hear them everywhere.
They kind of embody pop music because they had such
diverse tastes and because they were willing to try so
many different things.

Speaker 1 (17:51):
I think, especially within the group. You know, it's like
Big Boy was already the person that he knew he
wanted to be as like a performer as a rapper,
and like we've you know, the big Boy character and
the big Boy style performing has has existed since then
and kind of you know, grown in other ways. But
you know, he he has sort of this firm and
like like you mentioned, like Andrea is such like this

(18:12):
like very fluid type of performer. So it's been so
fascinating to kind of see the different angles he's taken
on who he is. You know, even just like the
year's leading up to this Flute album, Like it just
was the times we saw Andrea in public was like
you know, you would see someone share a photo on
like Twitter or Instagram. That was like ran into Andrea
three thousand at the airport and he was just playing

(18:33):
a flute. I mean, I'm curious, like what you sort
of you know, as we kind of I think so
much of the Outcast Prime era.

Speaker 2 (18:41):
Is still in the air. You know.

Speaker 1 (18:43):
It's like it's still kind of feels like feels like, hey,
a happened yesterday, so it feels like, hey, I still
number one.

Speaker 2 (18:49):
Somewhere.

Speaker 1 (18:49):
I'm curious where you think that sort of legacy will
continue on, especially as they get further and further away
from I'm assuming was their only reunion tour the other
do I would be very very surprised if they ever
did another. One would love to be surprised, but I
very highly doubt they will do it again. I guess, like,
where do you kind of see that sort of developing
in the years going forward, and like how that will

(19:12):
be maintained by outcasts, by the fans and by the
artists influenced by them.

Speaker 3 (19:16):
They're going to keep influencing everybody. Like you said, there's
little of them all over pop music. Every song that
we talk about seems to relate to outcasts and for
them to be so influential and yet not to have
any imitators, I mean, nobody tries to sound like them
because nobody can sound like them. And so I think
going forward, they're just going to get more influential and

(19:38):
inspire more different kinds of artists.

Speaker 1 (19:40):
Yeah, and after the break, we have Simon Valsick Levinson
to talk about Miss Jackson. We are joined now by
Rolling Stone w Music editor Simon Valsik Levinson. Simon thank
you for joining.

Speaker 4 (19:51):
Us, Hey guys to see us all.

Speaker 3 (19:53):
Thanks Simon.

Speaker 1 (19:55):
Do you remember sort of like the first time that
you heard Outcast and kind of like what they they
to music? The first time that you listened to.

Speaker 5 (20:02):
Them, taking it back to let's say, you know, like
the mid to late nineties, this is probably like nineteen
ninety seven, nineteen ninety eight, there was just nobody doing
it like Outcast. Like I remember, you know, hearing probably
the first Outcast record that I heard that really made
an impression on me. It was a Quemini listening to
that album and listening to just you know how much
like personality and style both Big Boy and Andre you know,

(20:23):
we're bringing to the table, how they kind of played
off of each other. It just it felt like it
was kind of outside of genre, it was its own thing.
It was just like this incredibly compelling thing, and I
was kind of hooked from you know, that point forward.

Speaker 4 (20:36):
I think, so we're a lot of other people.

Speaker 1 (20:37):
You know, with Stantonia, like where do you kind of
see that falling within the Outcast discography and like what
it did for them.

Speaker 5 (20:43):
It can be wild to think about how far Outcast
went over the course of a relatively short period of
time in the nineties. Right, Big Boy and Andre started
you know, makeing music together when they were teenagers in
Atlanta in the early nineties. Their first album came out
in nineteen ninety four. At that point, you know, that
was a time win for a lot of people hip
hop with something it happened, you know in.

Speaker 4 (21:00):
New York or LA.

Speaker 5 (21:01):
Right, they had to really you know, plant the flag
and remind people, you know, literally, Andre famously said at
the nineteen ninety five Source Awards, and you know, the
South has something to say. That was like a controversial
statement at that time. People were like whoa, Like wow.
Once they had kind of established that Southern app was
exciting and important, you know, all the things that we
know it is now, they immediately went to kind of
exploding and reinventing that blueprint that they had made themselves.

(21:25):
And I think, you know, from there it was like
every two years, Outcast would drop a new album that
was even more incredible than the one before it. That
kind of made it feel like the last thing they did,
which had felt kind of mind blowing and incredible, was
kind of yesterday's news, and they were on a whole
other planet. Now and they did that with at Aliens,
with the Quemini, and then in two thousand, I feel
like Stanconi was like the ultimate fruition of everything that

(21:47):
Andrea and Big Boy had been doing prior to that point.
It was like nothing else, you know, anyone had ever heard,
you know really.

Speaker 1 (21:53):
Yeah, especially Andrea like starting to explore more singing on it,
and I guess testing out sort of his own style.

Speaker 2 (22:00):
I'm kind of reinventing himself.

Speaker 5 (22:01):
Yeah, I mean, I think the thing that's amazing about
Atcast to me is like you have one of the
greatest rappers ever, Big Boy, who's just like an incredible rapper.
You have Andre who's also an incredible rapper, but who
was almost never felt, you know, content to just be
a great rapper, right. He was always, even from the beginning,
trying to kind of, you know, get to this higher philosophical, spiritual,
mystical plane. And he pushed that farther and farther with

(22:23):
each album, and you know, it got to the point
where by the time you get to Stanconia, you press
play on that album and it starts with Andre like
metaphorically burning the American flag over, like you know, hard
rock guitars and a funk beat, and it's like it's
you know, telling you you're you're kind of you're in
a different realm now, and you know that that album
encompasses so many different exciting styles. And you know, I
think Miss Jackson shows you that one of the styles

(22:44):
that Andre was interested in doing and Big Boy could
kind of go along with him to do was pop music,
you know, and they could they could really do that
as well as they could do anything else.

Speaker 3 (22:52):
Yeah, the transition from a Quemini to Stanconia Our Remember
is a really kind of shocking transition because everybody would
have been del I did with just a Quimini part too.
Everybody kind of wanted more of the same.

Speaker 5 (23:05):
Yes, That's the thing about out Kest was that I think,
you know, they were so committed to kind of reinventing
themselves with every album that they did kind of weave
you wanting more each time, right, So like if you
wanted more of that, you know, A Quemini was already
an album that was pushing beyond the box of straightforward
Southern hip hop to incorporate all kinds of funk and
soul and so many other things, right, But they weren't

(23:25):
you content to stop there? And I think I think
specifically Andrea was interested in doing even more than that.
Wanted to tear up the rule book like yet again
for like the third or fourth time in as many albums.

Speaker 1 (23:35):
You know, Yeah, and what is it about Miss Jackson?
I guess, like why is it? That song kind of
broke the way it did and kind of reaches my people,
is it did?

Speaker 5 (23:42):
It's a great song. It's only one of my favorite
Outcast songs. I don't know if it's my number one favorite,
but it is, I mean for sure, Like Miss Jackson,
I think was their first number one hit, right, it
was a It was a really exciting thing to see
like this, you know, if you had been kind of
following them and listening to them album after album to
hear that big Boy Andrea were capable of making up
hit like a song that people would sing along to
that you could hear coming out of like you know,

(24:03):
taxis and playing on the radio all the time. That
was kind of like a new thing for them that
they and they did that like so effortlessly and without
kind of like losing who they were. That it was
really exciting to see those two guys making a number
one song.

Speaker 2 (24:15):
Yeah, what is your number one?

Speaker 4 (24:16):
Outcast on Oh.

Speaker 5 (24:17):
My God, my personal number one song. I mean, it's
it's hard to they're also, I mean, out Guests were
such a great albums band that it almost feels like reductive,
you know, sorry to uh to reduce them to one song, right,
but for the purposes of this podcast, I mean for me,
you know, Bombs over a Backdad also on the same
album from Sanconia.

Speaker 4 (24:33):
That's the song that just like completely.

Speaker 5 (24:35):
Re scrambled my brain when I heard it, but still
just kind of like no other group really picked up
that torch, Like no one else is making that kind
of like psychedelic you know, drum and bassed hard rap
like at the same time on one song the way
that you know Andrea and Big Boy did there.

Speaker 1 (24:48):
Yeah, I was rereading your twenty fourteen interview with Andre
and how he mentioned the label wanted kid Rock to
do with the guitar solo on it, which just like
blew my mind, just like I cannot believe this as
a concept, like imagining the version of the world where
there's like the Bombs of our Bagdad featuring kid Rock.

Speaker 5 (25:03):
Yes, that's that's a classic moment of like, you know,
no offense to whichever you know A and R person
that was that idea. But that's like a classic moment
in like major label brain thinking where they're like, what
Outcast needs on their extract is a kid rock guitards That.

Speaker 4 (25:16):
Made sense to someone at some time in nineteen ninety ninety.

Speaker 3 (25:22):
But then part of the great est of Miss Jackson
we've been talking about is that it sounded nothing like
Outcast in terms of like what we already thought Outcast were.
I mean, we're talking about fore it. The first one
I ever heard was Rosa Parks, and it was so
different from anything anybody had done, so aggressively southern, so
rural as well as so urban, and just such a
mix of things that it just seemed like it was
completely insane. That it was like by you know, the

(25:44):
group that did elevators right, and that they were always
so committed, like you said, to just rewriting the rule
book every.

Speaker 5 (25:49):
Time, right, exactly, no, And they did that so many
times that it was almost it became like a game.
Listening to them, like what are they going to do
next time? How is this going to completely upend my expectations?
And you know, right now, I think for Andre three
thousand and that's you know, by doing what he's doing
now is something it's not even on just like a
it's on a whole different planet from what he did
with Outcast, and that's you know, it's exciting to see.

Speaker 2 (26:10):
Yeah.

Speaker 1 (26:10):
Yeah, even like I mean my introduction to them was
speaker Box the Love Below and kind of the bigness
of hay On and Roses and everything around the entire album,
and even that, you know, kind of going back afterwards
and hearing everything or like it just feels like such
like a different group each time. And of course like
at a wild after like that, it's just like it
feels like something completely different. Like the fact that they
were able to kind of keep it in a way

(26:31):
where each album is so much inventing themselves, Like it
does end up making sense that eventually, you know, Andre
kind of goes like completely left field and like try
something completely new. You know, it just felt like such
a different group every single time in a way.

Speaker 5 (26:43):
Yeah, that's a great point, and I'm glad you brought
up with Speakerbox to love Blow. That's another like an
even more successful album and an incredible album, but you
know that's obviously famously like an album that has two halves,
where you know, Big Boy and Andrea were on such
different pages that they had to make sort of two albums.
They couldn't make one album that contained both of their visions.
In retrospect, Stanconie is kind of the last time that
their diverging visions could be fit on one album and

(27:06):
could kind of work together. And I think, I mean
Mims Jackson is an example of that, right, Like you
can hear on that song, Andrea is stretching to you know,
do these these new things and to make a love
song and a heartbreak song and a pop song. Big
Boys is still there, you know, keeping keeping outcasts grounded
in the kind of the traditional kind of like clever
slick talking, you know, rap music that he's so excellent at,

(27:27):
and you hear both of their visions kind of for
one of the last times still kind of working together.

Speaker 2 (27:32):
Yeah.

Speaker 1 (27:32):
I love the way that you described Big Boys kind
of keeping outcasts sort of grounded in kind of what
they've like, what they've always done, and sort of what
the core of outcasts and who they are. I mean,
tell me about sort of your own kind of relationship
with his solo music sense and like what he's sort
of I mean, he's also had like I mean, I
feel like, just like such a fascinating journey since Outcast
has broken up and then reunited and then broken up again.

Speaker 5 (27:55):
But yeah, right, yeah, no, it's it's fascinating, like so
one interesting thing that happened with Outcast. You know, in
the nineties, I would say, there were always these debates
about who's the better rapper, Andre or a Big Boy,
And for many years people would kind of maybe would
would think that Andrea was the greater. And you know,
there's a strong case to be made there, right, He's
someone who has this kind of this other level to him,
who is constantly kind of like pushing and expanding at
the same time. I think you can make an argument

(28:16):
that Big Boy on his own, even you know, without
Andrea on his own, is an incredible, you know, top
category rapper. And I think he's shown that in his
solo career. Sir Lucius left Foot, the first Big Boy
album that he put out, is an example of how
you know, I think there was a real question for
him there, like can big Boy make a great album
without Andre pushing him to kind of you know, try
new things and expand and the answer.

Speaker 4 (28:36):
Is like, yeah, he can.

Speaker 5 (28:37):
Like that's just an incredibly fun, charismatic, kind of enjoyable
Southern rap album that you really shows that, you know,
big boy can hold his own and hold the spotlight.
And he's done that many times since then in his
solo career.

Speaker 1 (28:48):
And we've talked a lot about on this podcast, and
especially with bands like this or artists like this, where
their legacy is always evolving and the way that they
sort of interact with it is complicated and you know,
unique and Okay is a perfect example of that. I mean,
what do you sort of see as sort of the
future of Outcast legacy and influence? I mean, we were
trying to piece together artists that are more explicitly inspired

(29:09):
by them. It's so hard to pin down because no
one can really do what Outcast has done. So you know,
of course the influence is there and kind of looms
over everything, but there aren't any there's no one who
can do exactly what Outcasts was able to do. And
so I mean, I guess what do you kind of
see as the future of that legacy and influence over
the years.

Speaker 5 (29:28):
Yeah, No, it's s right right on one level, like
no one is outcast, no one can be outcast. At
the same time, I think that you can see their
influence in you know, almost just like the whole category
of music and pop music in terms of what you know,
a group can do, what two people can do, there
are so many, you know, at the time in nineteen
eighty eight or nineteen night nine, two thousand, it was

(29:49):
still controversial and kind of like challenging to say that,
you know, a rapper might want to sing on an
album instead of rapping, or might want to make funk
or rock or psychedelic music. Now that kind and we
kind of take that for granted and tons of artists
you know, do that and do great things at that.
It's not questioned anymore, and that's you know, that's a
way is something that I think Outke has kind of
opened the door to in a lot of ways.

Speaker 2 (30:09):
Yeah, yeah, Thank you so much for joining us today, Simon.

Speaker 4 (30:12):
Thank you so much for having me, Thank you anytime.

Speaker 1 (30:14):
Thanks so much for listening to Rolling Stones five hundred
Greatest Songs. This podcast is brought to you by Rolling
Stone and iHeartMedia. Rinnan hosted by me Britney Spanis and
Rob Sheffield executive produced by Gus Winner, Jason Fine, Alex
Dale and Christian Horde, and produced by Jesse Cannon, with
music supervision by Eric Seiler
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