Welcome back to the Deep Dive. Okay, so you sent
us just an enormous amount of source material
on, well, one of the most creative, but also
maybe one of the most corporately complicated
careers in recent music history. Just putting
it mildly, yeah. Today we're not just looking
at a rapper. We are trying to unpack Dwayne Michael
Carter Jr., who you know as Lil Wayne. He's really
a force of nature, isn't he? A cultural phenomenon,
a business figure, just this blueprint for modern
hip -hop influence. That's exactly right. Exactly
the mission here. We've got, what, three decades
of career to synthesize. It's a huge task going
from like the child prodigy Baby D all the way
to Wheezy F Baby, the guy who, you know, has
charted more songs than Elvis Presley. It's wild.
More than Elvis, yeah. Our sources cover everything.
His early start, the trauma, his artistic shifts,
that crazy commercial peak, the legal nightmares,
and importantly, his deep influence on music
today. It really is a life lived at warp speed.
And so much of it played out in public, even
the really vulnerable moments. So we're going
to trace it all. From his New Orleans roots,
that childhood genius mixed with tragedy, through
the whole cash money rise, founding Young Money,
the mixtape era, which was just revolutionary.
Groundbreaking, really. The Ty Carter albums,
and then those huge public battles, the legal
stuff, the health scares. It's a lot. It is.
It's complex, full of contradictions. So yeah,
let's start at the beginning, those early foundations.
Okay. New Orleans, Hollygrove, Uptown, September
27, 1982. That's where Dwayne Michael Carter
Jr. is born. Right. And the context there is
so important. His mother was only 19 and his
biological father. He left when Wayne was just
two. abandon the family. That absence is critical.
You really see it reflected in his name change,
right? Dropping the D. Exactly. It's intentional.
The sources are clear. He said he didn't want
the name Dwayne because his father was never
there. A total rejection. So Wayne isn't just
a stage name. It's like reclaiming his identity.
It really is. It's symbolic. And he often talked
about his stepfather, Reginald Rabbit McDonald,
who passed away as his real father. He even has
a tattoo dedicated to Rabbit. That focus on chosen
family, loyalty. You see that theme running through
cash money, young money later on. It starts right
there, yeah. But what's also striking from the
sources is this duality in his childhood. Before
the street element took over, he was genuinely
gifted academically. Yeah, I saw that. Gifted
program in elementary school, honor student,
drama club in secondary school. He played the
Tin Man in The Wiz. Right. That's the detail
people forget. He had this other path, this other
potential. Wrote his first rap at age eight.
But the environment, Hollygrove, it was tough.
And that environment led to him leaving high
school, right? Not because of grades. No, not
at all. He left Marianne Abramson Senior High
in 10th grade because his mother found a gun
he was carrying for protection. She pulled about,
basically, to get his GED instead. Survival first.
That's intense. And it leads directly to that
near -fatal incident in 1994. Yeah. The shooting.
He was only 12 years old. Self -inflicted gunshot
wound to the chest. And the story around that
has changed over time, hasn't it? It has. Initially,
it was reported as an accident. But years later,
in 2018, Wayne himself said it was actually a
suicide attempt. Apparently, his mother had told
him he had to stop rapping and those associations.
That conflict almost killed him. Just devastating.
But then there's this moment of almost grace.
The off -duty officer, Robert Hubler. Uncle Bob.
Uncle Bob, yeah. Wayne credits him with saving
his life. Hubler apparently insisted they rush
him to the hospital in the police car immediately,
didn't wait for an ambulance. That decision probably
made all the difference. Wow. So this mix of
raw talent and deep trauma, it seems to push
him straight towards music, towards Cash Money.
Absolutely. He's discovered by Brian Baby Williams
Birdman in 1991. Signs with Cash Money Records.
He's 11 years old. 11? Just a kid. A kid. He
starts off in a duo, the BGs, with BG. That's
when Wayne was Baby D. They put out an album,
True Story, in 95. But the real launching pad
was the Hot Boys, right? Definitely. 1997. Juvenile,
Turk, BG, and Wayne, the youngest member, only
14. They really established the cash money sound
and brand. Get it how you live. Then Guerrilla
Warfare in 99. That one hit the Billboard charts,
number five. Yeah, Guerrilla Warfare was their
major label debut. Had hits like, We on Fire,
I Need a Hot Girl. He basically grew up inside
the music industry machine, learned it all as
a teenager. Okay, so that sets him up for his
solo career, which, as you mentioned, started
strong commercially, but maybe critics weren't
fully on board yet. That's a good way to put
it. Fablock is hot. His debut in 99 when he was
17, platinum, hit number three on Billboard.
Huge start. But the next couple, Lights Out in
2000, 500 Degrees in 2002, they didn't quite
hit the same mark. Right. Both went gold, which
is still successful, obviously, but critically,
yeah, got a more lukewarm reception. Some critics
pointed out a, quote, lack of coherent narratives
in his verses. Like he hadn't quite found his
voice yet. Still kind of working within that
established hot boys cash money sound. Pretty
much. And 500 Degrees, that title alone tells
a story. It was a direct shot at Juvenile. who
had left Cash Money and had that massive hit
album 400 Degrees. Ah, so internal label beef
spilling onto the album titles. Classic. Yeah,
the tensions were already there. But even while
figuring out his solo identity, he stayed visible
with features. He was on that 3LW track, Neva
Get Enough, and of course he was on Juvedal's
huge hit, Back That Ass Up. Kept his name out
there. Kept him relevant while he was honing
his craft. And boy, did it pay off in 2004. Thug
Harder. Okay, this was the turning point. Absolutely
seismic. This wasn't just another record. Critics
immediately recognized it. A major advancement
in his rapping style and lyrical themes, they
said. This was the arrival. And visually, too,
right? This is when the dreadlocks appear on
the cover, signaling a whole new persona. Totally.
The look matched the sound. It sold nearly 900
,000 copies in the U .S. And Go Gijay was a big
hit, top five on the R &B hip -hop chart. Confirmed
the evolution was working commercially, too.
And he started getting these huge mainstream
features. Destiny's Child, Soldier with T .I.
That was massive. Huge. Peaked at number three
on the Hot 100. Put him right in the pop conversation.
Way beyond just hip -hop circles. So the creative
side is exploding, but he was also making moves
on the business side around this time. Yeah,
which is pretty remarkable for someone his age.
In 2005, he's actually named president of Cash
Money Records. President? Wow. 22. I'm three
years old. And he immediately uses that position.
Same year, he founds Young Money Entertainment
as an imprint of Cash Money and Universal. Smart
move. Building his own platform under the bigger
umbrella. That obviously pays off later with
Drake and Nicki. Hugely instrumental. Though
interestingly, he didn't stay in that president
role for too long. By 2007, he hands the day
-to -day management of Young Money over to Cortez
Bryant. Seems like he wanted to focus purely
on the music again. And that focus led to Ty
Carter II in 2005. Which debuted at number two.
Sold two million worldwide eventually. Big success.
But there's a really important behind -the -scenes
detail here. Manny Fresh wasn't involved. Oh,
wow. The main cash money producer. Why not? The
sources point to money issues. Financial disputes
with the label. Manny Fresh basically co -created
the whole cash money sound. And him leaving over
royalty problems. That was a major red flag about
how cash money operated financially. Problems
that, you know, would eventually catch up to
Wayne himself. It's like you can hear the foundation
starting to crack, even as the empire is growing.
Still, Ty Carter II had hits like Fireman, Hustler
Music. Yeah, strong singles. And then in 2006,
you get the collaboration album with Birdman.
like father, like son. And that gave us Stuntin'
Like My Daddy. Which became like an instant catchphrase,
cemented that whole mentor -protege narrative
they were pushing. Exactly. So that whole mid
-2000s period, it really set the stage for his
absolute peak. But the way he got there, it wasn't
the usual album cycle. He did something different.
The mixtapes. The mixtape revolution. This is
where things get really interesting because people
credit Wayne with basically changing the whole
game here. How artists stayed relevant, how hype
was built. Instead of just waiting for the next
album, he just unleashed this flood of material.
A plethora of mixtapes and guest appearances,
as one source put it. It was saturation, deliberate,
keep his voice everywhere. And some of those
mixtapes became legendary in their own right.
Dedication 2, Daryl Drought 3. Absolutely critical
works. They got massive media attention, critical
acclaim, because they showed just how hungry
he was. He'd take anyone's beat, any hit instrumental,
and just attack it, make it his own. Dedication
2 had that track Georgia Bush, right? Critiquing
the Hurricane Katrina response. Yeah, that was
a powerful moment. Showed he could use that lyrical
skill for serious commentary too, not just punchlines
about money and cars. It was raw, personal. And
Dale Drought 3, that was free. And he was rapping
over other people's hits. Yep. Released for free,
legal download. And the concept was audacious.
He's basically saying to the entire industry,
give me your biggest song right now, I'll rap
over it, release it for free, and probably do
it better. It was pure competitive fire. That
seems legally risky, even if it was free. How
did that strategy work so well? Because it created
insane buzz. Oh. It bypassed all the official
channels, radio, label promotion. It was pure
street -level demand. He was everywhere. All
the time, even without an official album. Rolling
Stone even called the Drought 3 one of the best
albums of 2007, even though it was technically,
you know, an unauthorized mixtape. Wow. So the
free content built massive anticipation for whatever
he charged for next. Exactly. It proved the model
could work. And it cemented his status as the
feature king. Right. He was popping up everywhere.
Fat Joe's Make It Rain got a Grammy nomination
for that. DJ Keld's We Takin' Over, Lloyd's You.
Big hits. His output was just. By the end of
2007, everyone recognized it. MTV called him
the hottest MC in the game. The New Yorker said
he was rapper of the year, GQ, workaholic of
the year. All that momentum built towards the
monster. That Carter III, 2008. But that album
had its own drama before it even came out, right?
Leaks. Oh, yeah. It was heavily leaked, delayed
multiple times. He actually had put out an EP
called The Leak in 2007, basically using some
of the leaked tracks just to get ahead of it.
But when it finally dropped in June 2008. The
numbers were staggering. Over a million copies.
Yeah. In the first week. Yeah. In the U .S. That
hadn't happened since 50 Cent's The Massacre
three years earlier. It wasn't just a rap album.
It was a full -blown cultural event. And the
singles were unavoidable. Lollipop, his first
solo number one on the Hot 100. Featuring Static
Major, yeah. Huge hit. And Got Money with T -Pain
was top ten too. The album just dominated. Led
to that big Grammy night too. Four awards. Yep.
including best rap album, best rap song for a
lollipop. His visibility was just total. headlining
festivals the vmas and didn't he perform at the
country music awards he did with kid rock yeah
first hip -hop act ever to perform at the cmas
showed how far his reach had extended just genre
-breaking influence okay so this is the absolute
peak but then things start to shift a bit he
puts out the young money compilation right we're
young money in 2009 certified gold gave us massive
hits like every girl and bedrock really launched
drake and nikki into the stratosphere and then
rebirth the rock album ah yes rebirth 2010. his
big experimental swing, released just before
he went to jail. And, well... It didn't go over
well. Generally negative reviews, yeah. Critics
mostly panned it. Some called it his worst album
since maybe 500 Degrees. It proved that even
Wayne's Midas touch didn't automatically work
across any genre he tried. But even going to
jail didn't stop him commercially. He released
an album while incarcerated. He did. I am not
a human being. Dropped on his 28th birthday in
2010 while he was serving eight months at Rikers
Island for that 2007 weapons charge. And it went
number one. His fifth number one album. Made
him the first rapper since Tupac in 95 to have
a number one album while locked up. It just shows
the insane loyalty of his fan base. They were
waiting no matter what. So he gets out and immediately
pivots back to the main franchise, that Carter
IV. Yep. Carter IV era begins. Which also, sadly,
kind of marks the beginning of the end of his
relationship with cash money. But Carter IV itself
was huge, right? Debuted at number one in 2011.
Huge. Sold 964 ,000 copies first week. which
is interesting because it actually outsold Jay
-Z and Kanye West's big collab album, Watch the
Throne, which had dropped earlier that summer.
Wayne still had the commercial edge. And this
is when he breaks that Elvis record. That's right.
September 27, 2012. He officially surpasses Elvis
Presley for the most songs ever. On the Billboard
Hot 100. 109 entries at that point. How did he
manage that? Was it just the features? It was
largely the features, yeah. And the mixtape tracks
that charted, it reflected the digital era, how
song consumption was tracked. Every guest spot
counted. His high volume strategy basically hacked
the chart rules of the time. He mastered that
system. And he was still everywhere on features.
Drake's Miss Me, the motto. Eminem's No Love,
Chris Brown, Kelly Rowland. Domination. But it
was around this time, 2012, 2014, that he started
talking about retirement, saying Thigh Carter
V would be his last album. Wanted to focus on
his kids, other interests. That promise. Didn't
exactly pan out smoothly. Not even close. First,
we got I Am Not a Human Being Tipped in 2013.
Mixed reviews again. Some critics felt the quality
was maybe slipping a bit, maybe fatigue setting
in. And then the wheels just came off with I,
Carter V. Late 2014, everything just stopped.
Ground to a halt. Wayne went public. Said the
album was done, but Cash Money and Birdman wouldn't
release it. Claimed they were holding him and
his music prisoner over money. This wasn't just
a delay. This was war. Full -blown legal and
financial war. The sources say he sued them for
$51 million in early 2015. Alleged they owed
him an $8 million advance for Carter V, plus
tons of unpaid royalties for him and Young Money
artists. His masterpiece was finished but locked
away. Just imagine that creative frustration.
But he fought back creatively too, right? With
mixtapes? Yeah, brilliantly. He dropped, sorry,
For the Way Too in 2015. And the whole mixtape
is basically just him dissing Birdman and Cash
Money over other people's beats, using the music
as his weapon. And he found a way around them
for distribution too, with Tidal. Exactly. He
became an artist donor at Jay -Z's Tidal platform.
And then he exclusively released the Free Wheezy
album there in 2015 under Young Money and Republic
Records. Completely bypassing cash money. A clear
act of rebellion. You could see the toll it was
taking, though, that tweet in 2016. Defenseless
and mentally defeated. Hinting at retirement
again. That was a low point. But the support
he got from other artists, from fans. It showed
how much people wanted him to pull through. And
eventually he did. Settlement reached in June
2018. Yeah, announced he was finally free from
cash money. And then finally, the iCarter V,
released on his 36th birthday, September 27,
2018. And the reception was huge, like a collective
sigh of relief. Absolutely. Deviated number one,
obviously. Massive streaming numbers. Second
biggest streaming week ever for an album at that
time, only behind Drake. The demand was just
incredible after all those years. It proved he
was still relevant. Every song charted. Every
single song on the album hit the Billboard Hot
100, and he debuted two songs in the top five
simultaneously. First artist ever to do that,
comeback complete. He showed that even nine years
of delays and legal battles couldn't erase his
star power. Okay, so post -settlement Wayne,
he hasn't exactly been taking it easy, has he?
Not at all. The work ethic seems hardwired. 2020,
he drops Funeral. Another number one album quickly
follows with a deluxe version featuring current
stars like Doja Cat, Lil Uzi Vert. Still connected.
And doing collaborations too, that mixtape with
Rich the Kid. Trust Fund Babies, yeah, 2021.
Apparently they knocked that out in like six
weeks. Just pure chemistry, back to that spontaneous
mixtape energy. What seems important in this
recent phase is also him kind of... organizing
his legacy, getting those classic mixtapes onto
streaming. That's crucial. Sorry, sorry. The
wait, no ceilings. Making that revolutionary
free work available and importantly, monetizable
now. Cleaning up the back catalog for the streaming
era. And fixing old credits like with the 2 Chainz
project. Right. Welcome to Call of Grove in 2023.
The sequel to their 2016 album, Call of Grove.
He wasn't credited as a main artist on the first
one because the cash money situation was so bad
then. The sequel corrects that. Puts him back
as an equal partner. We also got his first official
greatest hits album, I Am Music, last year. Had
that unreleased track with DMX2. Yeah. Can't
nobody. Nice touch. Connecting back. So what's
next? That Carter Sissix is confirmed. Confirmed.
And announced via a Cetaphil ad. Of course. Only
Wayne. June 6th, 2025, apparently. But beyond
that, there are still those legendary Sheld projects
people talk about. I can't feel my face. The
collab with Jewel Santana, that's been teased
forever. And Duvall, the album he wrote in jail.
Yeah, Duvall. Loved backwards. Supposed to be
an album of love songs written during his time
on Rikers Island. He confirmed back in 2013 it
was coming. Still waiting on that one. Very intriguing
prospect. And maybe the biggest sign of moving
forward. He publicly reconciled with Birdman.
January 2024. Pictures of them in the studio
together. It seems like that nine -year war is
officially over, which, you know, hopefully clears
the path for him to focus fully on this next
creative chapter. Okay, so the business drama
seems settled. Let's dig into the artistry itself.
What defines Lil Wayne's musical style? At its
core, it's that creative lyrical ability, like
the sources say, heavy use of punchlines, wordplay,
homonyms, metaphors, similes, and just relentless
braggadocio. Confidence bordering on arrogance
but backed up by skill. And his writing process
was key to that, right? The whole no pen, no
pad thing. Crucial. He credits Jay -Z with the
inspiration. Stop writing lyrics down. Just go
in the booth, hear the beat, and freestyle the
verses directly onto the track. What does that
do for the sound? What's the trade -off for working
that way? Well, it allows for incredible speed
and spontaneity. Those amazing, unexpected punchlines
often come from that immediate, in -the -moment
creation. It prioritizes flow and instinct. The
downside... Sometimes it can lead to verses that
maybe lack a tight structure or a clear narrative
arc. That's the criticism we saw sometimes, especially
later on. It's raw genius over meticulous polish.
His subject matter often courted controversy,
wealth, drugs, sex. But his influences were surprisingly
broad. Incredibly diverse. He calls Missy Elliott
his biggest musical inspiration. Says she influenced
everything I've ever done, which is fascinating.
Missy. OK, didn't expect that. Right. But then
you also have the expected ones. Goody Mob, Tupac,
Biggie. But also T -Pain, Prince, Lauryn Hill,
Arisa Badu. That eclectic taste definitely fed
into his ability to constantly morph his style
and flow. And that constant change, that innovation,
is his legacy, really. He's called one of the
most influential artists of the 21st century.
Consistently. And the greatest rapper of his
generation. Because he didn't just make hits,
he fundamentally altered the sound of hip -hop.
Specifically how? The sources mention autotune
and trap music. Yeah. His use of autotune was
key. It wasn't like T -Pain, who used it as a
full vocal effect. Wayne often used it more subtly,
almost as punctuation within his raps, on ad
-libs, on hooks, creating these melodic undertones.
And that influenced Trap. Hugely. That melodic
sensibility, combined with his unique cadences
and flows, became a foundational element for
the wave of Trap artists that followed, especially
out of Atlanta. He provided a sonic blueprint.
And the list of artists who say he influenced
them is just... Staggering. It's basically a
who's who of modern hip -hop. Drake, Nicki Minaj,
obviously he signed them. But also Kendrick Lamar,
Future, Young Thug, Lil Baby, 2 Chainz, Polo
G, the list goes on and on. He didn't just mentor,
he literally shaped the sound of the generation
after him. His hometown certainly recognizes
that impact. Key to the city of New Orleans.
Yep, November 2024 from Mayor Cantrell. And Master
P is starting a NOLA Walk of Fame, with Wayne
getting a Fleur de Lis plaque. Plus Lil Wayne
Day. February 6th and 7th now. Officially, in
New Orleans. From Holy Grove kid to civic icon,
it's quite the journey. To really grasp the whole
picture, though, we need to touch on his public
life outside of music. The family, the health
issues, the legal stuff. Yeah, the complexities
don't stop with the music. His family life has
always been very public. Four kids, four different
partners. Daughter, Reginae, with Toria Johnson.
His high school sweetheart and ex -wife. Right.
Married 2004 -2006. But sources say they remain
close. Good co -parents. then his sons, Dwayne
III with Sarah Vivan, Cameron with actress Lauren
London, and Neil with the singer Nivea. And the
timing there was complicated, wasn't it? London
and Nivea pregnant around the same time. Yeah,
2009. Highlights that very modern, blended family
structure he's navigated throughout his fame.
And now his son Neil, Lil Novi, is making music
too. The legacy might continue. What about his
personal beliefs? He identifies as Catholic.
He does, yeah. often references God or Jesus
in his music and performances. Educationally,
he did try college briefly, University of Houston
in 2005, but his sigil's too crazy. Later took
online psychology courses with University of
Phoenix. Psychology. Interesting choice given
everything he's been through. Maybe trying to
understand it all. He's also a huge sports guy,
beyond just being a fan. Packers, Bruins, Lakers.
But he owns a sports agency. Brought one, yeah.
Renamed it Young Money APA Sports. And he's involved
in sports media, too. Did the theme song for
Skip and Shannon's show, Undisputed. Pops up
as a guest. He's just woven into the cultural
fabric. Okay, let's talk about the health scares.
The seizures. Those started becoming public around
2012. Yeah, reports of his private jet making
emergency landing. Then the really serious incident
in 2013. Hospitalized. Critical condition. And
that's where the conflicting reports came in.
TMZ blaming Purple Drink, codeine abuse. Right.
But his team, Mac Main, Birdman, they pushed
back hard, slammed TMZ, said the drug angle was
exaggerated and that these seizures were an ongoing
issue. Epilepsy. So drug -induced versus a medical
condition. How do we reconcile those? Well, we
have to report both claims. But it's significant
that his management, people close to him, consistently
denied the primary cause was drug abuse. framing
it as a pre -existing neurological condition.
And whatever the trigger for specific episodes,
the long -term diagnosis seems clear. Wayne himself
has confirmed he has epilepsy. And acknowledged
it affects his memory now, trouble remembering
his own songs. Yeah, he mentioned that in 2023.
That's a profound impact for a lyricist known
for such intricate wordplay. a really difficult
consequence of the condition. Finally, the legal
and political side. We know about the 2007 -2008
arrests leading to the Riker sentence in 2010.
And then the more recent federal firearms charge
in Florida in late 2020. He pleaded guilty. This
was around the time he met with then -President
Trump about criminal justice reform. And Trump
pardoned him. Yep. On January 19, 2021, one of
Trump's final acts in office wiped that charge
clean. He also caught heat for that flag incident
in the music video. The God Bless America video
in 2013. Yeah, the visual of him seemingly stepping
on the U .S. flag caused a big backlash. What
was his explanation? He said it wasn't meant
as disrespect. The idea was the flag drops to
the ground, revealing the hoods of America behind
it. A visual metaphor that didn't land well for
many people got interpreted as desecration. And
then his comments on Black Lives Matter in 2016,
those are really controversial. Extremely. He
basically said he didn't feel connected to it.
A damn thing that ain't got nothing to do with
me was the quote, I think. Why did he feel that
way? His reasoning was personal. He said, look
at me. I'm a rich black man. I have white fans.
That proves black people are valued. It was a
very individualistic, almost libertarian take.
Success negates the need for collective movements.
Drew a lot of criticism, but it's consistent
with his self -made ethos, I suppose. OK, so
we've traced this incredible arc. Child star,
mixtape innovator, chart -topping mogul, legal
warrior, influential icon. What's the big takeaway
here? I think the key takeaway is that Lil Wayne
really is a blueprint. Over 120 million records
sold. He pioneered using free content to drive
mainstream success. He built an empire with young
money that shaped the next ways. He fundamentally
changed the sound of modern hip -hop, especially
trap. And he did all this while navigating...
Unbelievable internal industry conflict, major
health issues, legal jeopardy. His creative output
somehow thrived in the chaos, maybe even because
of it sometimes. It really makes you wonder about
creative resilience, doesn't it? How do you keep
that fire going, keep innovating, keep freestyling
those verses when the structures around you are
seemingly trying to hold you back, that sheer
will to just get the music out, no matter the
format? That seems to be his defining trait.
Absolutely. And that story isn't over. We mentioned
those unreleased projects. Yeah. I can't feel
my face with jewels and especially devil. Those
introspective love songs from Rikers. Yeah, considering
how his last big experiment, Rebirth, was received
critically, it poses a really interesting final
thought for you, the listener. What would the
successful release on a project like The Vole,
something potentially quieter, more reflective,
born from incarceration, actually mean for Lil
Wayne's legacy? Could the love songs from Jail
finally reveal a critically embraced, perhaps
more peaceful version of Wheezy? Or does his
audience, and maybe even his own creative spark,
ultimately need that chaos that fueled so much
of his legendary run?