You know, we talk about potential a lot in these
deep dives. Usually it's about a tech startup
that almost made it, or maybe a movie that got
stuck in development hell. It's usually this
abstract thing. Sure, there could have been stories.
The ones that got away, they're always fascinating.
Exactly. But in music, potential is, well, it's
usually a nice way of saying, didn't quite make
it. You know, oh, they had so much potential,
which is really just code for they had one good
song on the radio in 2004 and then poof, they
vanished into the ether. It's the one hit wonder
syndrome. Or you see it with a band that puts
out a classic first album and then just breaks
up before the second one, that kind of thing.
But today, today's Deep Dive, it feels really
different. I was reading through just the massive
stack of research you sent over. And by the way,
thank you for the extra material on that ethylene
book, which we absolutely need to talk about.
Oh, for sure. That's a crucial piece of the puzzle.
Reading all of this, I genuinely got angry. Angry.
That's a strong reaction. Not usually the one
we aim for. Yeah. No, it was. It was frustration.
Because we were looking at a story where the
potential wasn't theoretical. It wasn't a maybe.
It was literally. It was being signed on a piece
of paper. It was days away. It was imminent.
Yes. We aren't talking about a guy who might
have become a star. We're talking about a guy
who was standing on the absolute threshold of
becoming the king of New York, arguably a billionaire
mogul right alongside Jay -Z, and then the door
just slammed shut. That is the perfect way to
frame the tragedy of Lamont Coleman. Better known
to the entire world as Big L. The punchline king.
The lyricist, a legend's legend. But see, here
is the tension I want to start with, because
I really need you to explain this to me. If I
look at the stats, just the raw numbers, Big
L released exactly one studio album while he
was alive. Just one. One. And it peaked at number
149 on the Billboard 200. Which, statistically
speaking, in the major label system of the 1990s,
is a commercial flop. There's no other way to
put it. Right. So if I'm an alien landing on
Earth and I'm just looking at the spreadsheets,
Big L is a footnote. He's a blip on the radar.
But if I talk to Nas, if I talk to Jay -Z or
Eminem, they talk about this guy like he's a
deity. A force of nature. Miles literally said
he was scared to death to rap against him. So
what is the disconnect here? That's my mission
for this deep dive. I want to understand how
a guy with a quote unquote failed debut album.
became a hip hop god. And we are absolutely going
to bridge that gap because to understand Big
L, you can't look at the sales figures. That's
the wrong metric. You have to look at the mechanics,
the actual science of what he was doing with
words. The technique. The technique. We're going
to talk about something later on called compounding.
It's a rhyme technique that he had mastered before
almost anyone else was even attempting it. And
we have to talk about the what if, the giant
looming what if of the Rockefeller deal. It might
be the biggest what if in all of hip hop history.
We have sources today, including that biography,
Ethylene, you mentioned, and some very recent,
very controversial updates from 2025 that paint
the picture of a guy who is about to merge his
untouchable underground credibility with Jay
-Z's unstockable commercial machine. And we're
also going to get into the darkness. Yeah. I
mean, you can't tell this story without talking
about 139th Street, the danger zone, and the
cold case murder that went unsolved for decades.
And the prevailing theory that it wasn't just
random street. violence, that it was a specific
targeted hit involving a complex, almost Shakespearean
web of family loyalty and ultimately betrayal.
It's a heavy one today, but it's a necessary
one. Absolutely necessary. He's too important
to be just a footnote. OK, let's drop the needle
then. Take us back. Who was Lamont Coleman before
he was a legend? To understand Lamont, you really
have to understand the geography first. He was
born May 30, 1974, Harlem, New York City, specifically
139th Street between Lenox and Fifth Avenue.
And 1974. I mean, New York is a completely different
planet back then. It's not the tourist -friendly,
sanitized Times Square you see today. Oh, not
at all. It's gritty. It's dangerous, especially
in certain neighborhoods. But it's also incredibly
vibrant. It's the incubator for what hip -hop
is about to become. And Lamont was the baby of
the family. The youngest of three. The youngest
of three, yes. His mother was Gilda Terry and
his father was Charles Davis. But, and this is
a common story for that era, the father leaves
the picture very early on while Lamont is still
a child. So it's essentially a single mother
household. Mostly, yes. But the real dynamic
you need to pay attention to is the siblings.
He grew up with two older half -brothers, Donald
and Leroy Finazzi. Finazzi. Okay, that name is
important. And these brothers, they aren't just
background characters, right? They're not just
names on a family tree. No, absolutely not. They
are, in a way, the bookends of his life. One
of them, Donald, introduces him to the dream
that will make him a star. And the other, well,
the other, Leroy, is inextricably tied to the
nightmare that ends it all. But we'll get there.
So as a kid, he's little Al. He's Montmont. Just
a neighborhood kid. Every superhero has an origin
story. You know, a radioactive spire bite or
a traumatic event in an alleyway. What was Big
Al's radioactive spider? It was a ticket stub.
A ticket stub? Seriously? It was 1981. Lamont
is just seven years old, and his big brother
Donald takes him to the Beacon Theater. The Beacon.
That's a legendary venue on the Upper West Side.
Who was playing that night? Run DMC. Oh, come
on. At seven years old, I was eating paste and
watching cartoons when I was seven. He's at a
Run DMC concert. Well, Lamont was getting a very
different kind of education. I mean, try to imagine
that. It's 1981. Hip -hop is still young. It's
raw. It's electrifying. And you're a seven -year
-old kid from Harlem seeing Run DMC and Jam Master
Jay on stage, controlling a crowd of thousands
of people with just two turntables and a microphone.
It must have been like seeing magic for the first
time. That's exactly how his brother described
it. Donald said that Lamont didn't just enjoy
the show, he was awed by it, completely mesmerized.
It's one thing to see the trick, but it's another
to want to know how it's done. Precisely. It
flipped a switch in his brain. Donald said from
that moment on, Lamont was different. He wasn't
just passively listening to the music anymore.
He was studying it. He was deconstructing it,
trying to figure out the rhyme patterns, the
cadences. I just love that image. The little
seven -year -old scholar of rhythm in his bedroom.
So he starts practicing early. Very early. By
the time he's 12 years old, he's not just playing
tag in the streets. He's freestyling with his
neighbors. He's... Battling people on the block,
older kids, anyone. And around 1990, he starts
officially writing his rhymes down. And this
is where we see the first real sign of his personality
type, his drive. What do you mean by that? Well,
he doesn't just want to be good. He wants to
be organized. He forms a group. He does. In 1990,
he founded a group called Three the Hard Way.
Three the Hard Way. That has some very 90s action
movie energy to it. I love it. It was him, a
guy named Doc Ream, and another guy named Rodney.
But the group implodes almost immediately. Ah,
the classic creative differences. Not even that,
really. It was a lack of hustle, at least from
his perspective. The other guys just didn't care
as much as he did. They treated it like a fun
hobby on a Friday night. He treated it like it
was his career already. He was a professional
at 16. Mentally, yes. So Rodney left. They tried
to rebrand the remaining duo, him and Doc Ream.
And what did they call themselves? Two Hard Motherfuckers.
Okay, very subtle. I like it. A branding consultant's
nightmare, but I respect the directness. Not
exactly a radio -friendly name for 1990, no.
But that group folded, too, for the same reason.
And I think this is a crucial character moment
for him. How so? Big L looks around at his friends,
at the people he came up with, and he has this
powerful realization. If I wait for anyone else
to be as hungry as I am, I'm going to starve.
It's a very profound and kind of lonely realization
for a teenager to have. It is. So he decides
to go solo. And he decides to take a massive,
massive risk. This is the Cinderella moment you
mentioned at the top of the show. This is my
favorite part of the story. Because the sheer
audacity required. I get sweaty palms just thinking
about doing this. Okay, so it's the summer of
1990. Picture it. 125th Street in Harlem. There's
a record shop, Rock and Will's Records, and the
legendary Lord Finesse is inside, signing autographs
for his new album. And just for our listeners
who might not have a PhD in 90s rap hierarchies,
who is Lord Finesse in the ecosystem at that
specific time? He is a titan. He's one of the
most respected lyricists out, a top -tier producer,
and a key figure in the Bronx and Harlem scene.
He is, for all intents and purposes, a gatekeeper.
If Lord Finesse co -signs you, you exist. If
he ignores you, you might as well be invisible.
So the scene is set. It's summer in New York,
so it's probably hot. It's loud. There's a line
of fans snaking through the store. Everyone is
probably holding a vinyl record, asking for a
signature, maybe stammering, I love your work,
man. Then up to the front of the line walks this
teenager, Lamont Coleman, 16 years old. He doesn't
ask for an autograph. He doesn't have a record.
He looks Lord Finesse right in the eye and asks,
can I rap for you? See, that is just insane.
Because usually... Famous rappers hate that.
It's annoying. Hey, man, listen to my mixtape.
It's the punchline of a bad joke in hip hop.
99 times out of 100, the security guard just
steps in and pushes the kid away. But for some
reason, maybe it was the look of pure confidence
in his eye. Maybe finesse was just bored. He
says, all right, go ahead. Show me what you got.
And Big Al opens his mouth. And he doesn't stumble.
He doesn't do some simple nursery rhyme rap.
He spits a freestyle that is so complex, so full
of multisyllable rhymes and clever punchlines
that Finesse doesn't just listen for 10 seconds
and wave him off. He kept listening. He stopped
everything. He listened to the whole thing. He
was so impressed that he exchanged phone numbers
with the kid right there on the spot. That's
the modern day equivalent of walking up to Steven
Spielberg. Pitching a movie idea in a coffee
shop and walking out with a producer credit.
This doesn't happen. It really is. And just like
that, with one freestyle, he's in the game. By
1991, Lamont Coleman, now officially going by
Big L, is inducted into Lord Finesse's legendary
collective, the Diggin' in the Crates crew, or
DITC. Which is not a small thing. DITC is a super
group of talent. You've got Finesse, you've got
Showbiz and AG, Diamond D later on, Fat Joe and
OC join. He fell in with the absolute heavy hitters
immediately. And this brings up a really interesting
point about the barrier to entry in the 90s versus
today. Oh, it's a huge difference. Today, you
can just upload a song to SoundCloud or make
a video for TikTok. If the algorithm likes you,
you're famous, you don't need anyone's permission.
You can record a hit song in your bedroom. Exactly.
But back then... It was gladiatorial. There was
no internet to hide behind. You couldn't go viral.
You had to physically stand in front of a gatekeeper,
a person who knew more than you, who was better
than you, and prove in real time that you were
better than everyone else trying to get their
attention. You had to be undeniable, right then
and there. No autotune, no second takes, no editing.
And Big L thrived in that environment. That was
his element. He went to Julia Richmond High School,
graduated in 92, but his real education was happening
in the hallways and on the street corners. He
said in his last interview, in the beginning,
all I ever saw me doing was battling everybody
on the street corners, rhyming in the hallways,
beating on the wall. It was a sport to him. It
was his version of playing basketball. It was
more than a sport. It was combat. And that combat
mentality is what directly led to the development
of his specific, unique style. You mentioned
compounding earlier. Yeah, let's dig into that.
Because critics and rappers always talk about
his razor blade flow. What specifically was he
doing with words that was so different? Because
to an untrained ear, sometimes rap just sounds
like rap. Okay, so a very simplified explanation
is that most rappers at the time, and even most
rappers now, use what we call end rhymes. You
say a sentence, and the last word of that sentence
rhymes with the last word of the next sentence.
Simple. Cat had that. Simple, effective. I went
to the store, I wanted to buy some more. Easy
to follow. Right, it works. But Big L didn't
do that. He used compounding. He would stack
internal rhymes, multisyllabic rhymes, and metaphors
all on top of each other, rapidly, often within
the same single bar of music. So he's rhyming
the middle of the sentence with the end of the
next run, all while setting up a punchline that's
going to hit you three bars later. So it's like
he's playing 3D chess with words while everyone
else is still playing checkers. That's a perfect
analogy. It's incredibly dense. It's the kind
of rap you have to rewind the tape three or four
times just to catch everything he said. Critics
called it a lyrical snick up. He was basically
undressing his competition with words. I read
one review, I think it was from MF DiBella at
AllMusic, who described his flow as having a
razor blade under the tongue. That is such a
vivid and accurate description. It implies that
if you get too close, if you try to battle him,
you're going to get cut. And he was cutting people
left and right. But being that skilled, that,
I guess, that aggressive with his lyrics, it
kind of led him into a trap, didn't it? With
that first single, Devil's Son. It did. This
is where the story takes a very weird and defining
turn. This is 1993. He releases a promo single
called Devil's Son. Now, for people who haven't
heard this track, it is intense. Intense is a
very polite word for it. It's graphically violent.
It's got occult themes. It's basically a slasher
movie on a beat. It really is. The lyrics are
shocking, even by today's standards. Was Big
L a devil worshiper? Was he trying to start some
kind of satanic cult in Harlem? No, not at all.
And this is the great misconception that followed
him for years. He explained it later in interviews.
He was just a huge fan of horror flicks. He loved
watching Halloween, Friday the 13th, A Nightmare
on Elm Street. The classic 80s slashers. Exactly.
And he looked at his own reality, the very real
violence he saw in Harlem, the poverty, the desperation.
And he just combined the two. He said he wanted
to put it all together in a rhyme. So it was
cinematic? It was just... another form of storytelling
for him. It was. But because he was so damn good
at it, so convincing, the industry looked at
that one song and said, OK, we know what he is.
This is the horrorcore guy. Horrorcore. Just
the name of that subgenre sounds niche and limiting.
It is. It's a subgenre focused on graphic violence,
supernatural horror, the macabre. You can think
of groups like the Gravdegaz or early 3 -6 Mafia.
Big L inadvertently became a pioneer of a genre
that he didn't actually want to belong to. It's
like a brilliant actor who plays a villain just
one time, but does it so well that nobody will
ever hire him to play the romantic lead again.
That is a perfect analogy. He felt completely
boxed in by it. He wanted a show he could do
everything. He could make party tracks. He could
tell stories. He could battle rap. Devil's Son
cast this long, dark shadow over his early career.
But he kept grinding. Regardless, he made an
appearance on Yo! MTV Reps in 92, which was the
absolute holy grail of exposure for a rapper
back then. He was on a remix of a Lord Finesse
track, Yes You May, and he had a standout verse
on Represent from Showbiz and AG's classic album.
He was making all the right moves. And then he
won that amateur freestyle battle hosted by Nubian
Productions. Yes, that was a huge moment for
his street credibility. How many people were
in that battle again? 2 ,000. 2 ,000 contestants.
And he won the whole thing. He was the last man
standing. And that just reinforces the level
of skill we are dealing with here. This wasn't
hype from his friends. This wasn't a marketing
gimmick. This was empirical evidence that he
was the sharpest blade in the entire drawer.
And all of this momentum, the DITC affiliation,
the battle wins, it finally led to a major label
deal with Columbia Records. Signed in 1993. And
that led to the debut album in March of 1995.
Lifestyles of Depor and Dangerous. An iconic
title. An iconic album cover. One of the best
of the decade. But not iconic sales. Yeah. Not
even close. No. And this is where the story just
gets so frustrating. Let's really talk about
that disconnect. It's 1995. This is a golden
era. for New York hip -hop. You have Biggie's
Ready to Die. You have Wu -Tang's 36 Chambers.
You have Nas' Illmatic. Hip -hop is selling millions
of records. Why did Big L's debut album come
out and only hit number 149? That's barely charting.
It's a mix of a few crucial factors. First and
foremost, you have to look at the label, Columbia
Records. They were a massive pop and rock label.
They knew how to sell a Michael Jackson or a
Bruce Springsteen record. I honestly don't think
they had any idea what to do with an artist like
Big L. So the marketing was just completely off.
The marketing was practically non -existent for
the mainstream audience. He wasn't making radio
friendly hits like Big Papa or Juicy. He was
making gritty, complex, lyrical. underground
street rap, the kind of stuff that... ditc was
famous for the underground loved it though the
streets knew what it was oh absolutely but in
1995 if you didn't have a glossy high budget
video on mtv and heavy rotation and a catchy
hook sung by an r b singer you weren't moving
a million units it was just that simple and big
l wasn't willing to compromise on that was he
he wasn't going to make that kind of record no
he was a purist and that's why we respect him
so much today but it's also why he didn't sell
back then by the year 2000 five years after its
release the album had only sold about 200 000
copies which is respectable for an indie artist
today but for a major label signee in the cd
era boom that's a failure in the eyes of the
executives it's a massive failure and that failure
led to the inevitable in late 1996 he gets the
phone call he's been dropped from colombia the
dreaded artistic differences which is almost
always just industry code for you didn't make
us enough money Big L put it a lot more bluntly
in an interview. He said, I was there with a
bunch of strangers that didn't really know my
music. So now he's at a major crossroads. He's
been to the mountaintop. He was signed to a legendary
label. And now he's been kicked off. Most rappers
at that point would just quit. They become bitter,
fade away, and blame the industry. But Big L
had that hustler mentality from the streets.
He didn't complain. He pivoted. In 1998, he founded
Flamboyant Entertainment. His own independent
record label. His own label. And listen to his
business model because it's absolutely brilliant.
He told the Village Voice in an interview that
he planned to distribute the kind of hip -hop
that sold without needing top 40 samples or R
&B hooks. So he was doubling down on his style.
He was basically saying, I'm not going to change
my music to fit the market. I'm going to find
the market that fits my music. He was creating
his own lane. And that bet paid off almost immediately
with one of the most important and ingenious
songs in hip -hop history. Vap -hop history.
Oh, man. Ebonics. Criminal slang. If you haven't
heard this song, you need to pause this deep
dive right now and go listen to it. It was literally
a dictionary said to a beat. It is linguistic
anthropology. It's a master class in code switching.
He breaks down African -American vernacular English,
or AAVE slang, term by term, for two and a half
minutes straight. Brand new car is a new wheel.
If you're broke, you're on your last meal. Coca
-Cola is Coke. Crack is rock. The feds is the
pigs. The joint is the box. It's educational,
but it also slapped. It was catchy as hell. It
was pure genius. The Source magazine named it
one of the top five independent singles of the
year. The playwright Idris Goodwin later called
it the best example of L's impressive command
of the English language. It proved unequivocally
that he didn't need a major label to make a hit.
He just needed his voice and a good beat. And
that independence, that incredible buzz he created
all on his own from the ground up that attracted
the Sharks in a good way this time. Enter Damon
Dash. The co -CEO of Rockefeller Records. And
we need to really set the context here. What
is Rockefeller in 1998, early 1999? They are
the New York Yankees of rap. They are the empire.
Jay -Z has just released Volume 2, Hard Knock
Life. The single is a global phenomenon. He's
not just a rapper anymore. He's a certified superstar.
And Rockefeller is looking to expand. They want
to corner the entire market. And Dame Dash sees
Big L's independent hustle with Ebonics. He sees
a guy who has the raw, uncut street credibility
that Jay -Z respects, but also the buds and the
lyrical talent that can make them even more money.
He wants to sign him. This is the moment. This
is the what if. Big L is sitting across the table
from the hottest, most powerful label in the
world. He could have just signed on the dotted
line, taken the check and bought a mansion. He
could have. It would have been the easy thing
to do. But he had a condition. And this tells
you everything you need to know about his heart
and his loyalty. What was the condition? He insisted
that his crew, a group he had formed called the
Wolfpack. It was Irv McGruff, C -Town, and Stan
Spippe signed to Rockefeller as well. If I eat,
we all eat. He was bringing his whole team with
him. Exactly. He wasn't going to leave his friends
behind in Harlem. He basically told Damon Dash,
I'm not coming alone. It's all of us or none
of us. That is such a risky move. Yeah. Usually
a label in that position of power would just
say, no thanks. We just want you the star. Usually,
yes. But Rockefeller wanted Big L so badly that
they agreed. They were moving forward with signing
the entire group. And Jay -Z himself confirmed
this later, right? This isn't just a rumor. No,
it's a fact. Jay -Z said in an interview, quote,
we were about to sign him right before he passed
away. It was a done deal. A done deal. Let's
just pause for a second and imagine that record
label roster. You have Jay -Z at the peak of
his powers. You have Memphis Bleak. You have
Beanie Siegel. And you add Big L to that lineup.
It completely changes the entire architecture
of early 2000s hip hop. Does Big L challenge
Jay -Z for the throne? Do they become a dual
superpower like the Steph Curry and Kevin Durant
of rap and just dominate everything? Or do their
egos clash? It creates a super team before super
teams were even a thing in sports. The lyrical
talent on that label would have been frightening.
It would have been an arms race that nobody else
could win. And the contracts were being drawn
up. The process to sign the whole group officially
started on February 8th, 1999. February 8th,
okay. Keep that date in your mind. The pen is
hovering over the paper. The dream is finally,
finally happening. And then, one week later,
February 15th, 1999. We have to go there. 45
West, 139th Street, right in his own neighborhood.
It was a drive -by shooting. Big L was walking
near his home. A car pulls up. He was shot nine
times. Nine times. In the face and chest. It
was brutal. It was personal. It was not a robbery
gone wrong. They didn't take his jewelry, which
was worth a lot of money. They didn't take his
wallet. It was a targeted execution. That level
of violence nine times. That implies hatred.
That implies they were sending a message. It
does. It was meant to be a definitive brutal
end. So immediately the NYPD is involved. Who
did they look at as the primary suspect? Almost
immediately, the investigation focused on a childhood
friend of Lamont Coleman's, a guy named Gerard
Woodley. A friend? Someone he grew up with? They
grew up on the same block, but the police theory
was that this was an act of retaliation. but
not for something that Big L himself had done.
This is the part of these stories that's always
so tragic. The successful artist gets pulled
down by the people and the problems they were
trying to escape. The police believed it was
retaliation for something Big L's older brother,
Leroy Fenazzi, the one known as Big Lee, had
done or was believed to have done. So Big L was
a proxy target. He was killed to send a message
to his brother. That was the working theory for
a very long time. We can't get to the brother,
so we get to the famous rapper. But they did
arrest Woodley, right? They arrested him three
months later. But here is the problem with street
crimes in that era. Evidence. And witnesses.
People in the neighborhood don't talk to the
police. Witnesses suddenly can't remember what
they saw. Woodley was released due to a lack
of evidence. The case went cold. And it stayed
cold for a very long time. For years. For decades.
It was just another unsolved Harlem murder. And
Gerard Woodley. He didn't exactly get a happy
ending out of this either. No. What happened
to him? Gerard Woodley was killed himself in
2016. Shot in the head in Harlem. Live by the
sword, die by the sword, I guess. It seems that
way. And even then, things remained murky. The
rapper Cameron, who grew up with and knew both
of them very well, posted a video after Woodley's
death claiming that Big L had actually attempted
to have Woodley killed a week before L's own
death. Wait, what? That turns the entire narrative
on its head. But that just sounds messy. That
sounds like street rumors. It is incredibly messy.
And for a long, long time, that's all it was.
Rumors, street talk, whispers. Until 2017. 2017.
A book is published. It's called Epheline, The
Rise and Fall of the 139th St. NFL Crew. Written
by an author named Lou Black. And who is Lou
Black in this story? He was Gerard Woodley's
cousin. So this isn't a journalist speculating
from a desk in midtown Manhattan. This is coming
from inside the circle. This is family business
being aired out for the world to see. And the
story this book tells, it's not just a simple
case of retaliation. It's much more specific
and much, much darker. It is. The book alleges
that Big Lee El's brother was in prison at the
time of these events. And from his prison cell,
he allegedly hired a hitman to take out Gerard
Woodley and some of his associates on the street.
Okay, so the brother, Big Lee, orders a hit from
jail. Where does Big El fit into this alleged
plot? This is the part of the story that just
hurts to read. The allegation in the book is
that Big El Amant was tasked by his older brother
with identifying the targets to the hired hitman.
He was supposed to be the spotter. Oh, wow. So
in this version of the story, he isn't just an
innocent bystander caught in the crossfire. He's
an active participant in the plot. According
to this account, yes. The story goes that on
the planned day of the hit, Woodley noticed he
was being followed and watched. He got spooked
and the hit failed. But later that day. Woodley
allegedly saw Big L with the man he recognized
as the hitman. He put two and two together. He
connected the dots. Exactly. In that moment,
he realized, my childhood friend Lamont just
tried to have me killed for his brother. And
the implication of the book is? The implication
is that Big L was killed a week later to prevent
another attempt on Woodley's life. It was a preemptive
strike. That is just heartbreaking. Because it
takes this larger than life legend figure and
reminds us that he was still a human being, a
young man living in what was essentially a war
zone. It complicates the narrative so much. We
want our heroes to be pure and untouchable. But
the reality of 139th Street in the 90s didn't
allow for that kind of purity. He was caught
between two worlds, the lyrical prodigy world
where he was about to sign with Jay -Z and the
violent, unforgiving reality of his family dynamics
and neighborhood ties. And the ultimate tragedy
is that he was so close to getting out for good.
One week. If he signs that deal a week earlier,
maybe he moves to a mansion in New Jersey. Maybe
he's on a tour bus in another state. Maybe he's
alive today and the entire history of modern
music is different. So Big L is gone in 1999.
But the weird thing about music is... Sometimes,
death is just a career move. It sounds incredibly
cynical to say, but in the music business, it's
often true. And his posthumous career is almost
as robust and successful as his living one. In
August of 2000, his manager, Rich King, managed
to put together a posthumous album, The Big Picture.
And just look at the difference in the commercial
reception. His debut album flopped. The Big Picture.
It was certified gold. 500 ,000 copies sold.
It debuted at number 13 on the Billboard 200.
It had guest features from Tupac, Fat Joe, Big
Daddy Kane. It was treated like the coronation
he never got in life. And the single Flamboyant,
a track he released independently before his
death, it became a number one hit on the Billboard
Hot Rap Tracks chart. His only number one single.
It's a perfect, tragic example of the mainstream
finally being ready for him just a few years
too late. And the releases didn't stop there.
Over the years, we've seen compilations, unruly
tracks. But let's fast forward to 2025. This
is where it gets really interesting for our listeners
who might think the story ended 20 years ago.
Right. 2025 has been a massive and somewhat controversial
year for the Big L legacy. In April of 2025,
Nas announced that his company, Mass Appeal,
was launching a Legend Has It series to preserve
the legacies of hip hop icons. And Big L was
one of the first artists mentioned. Nas is essentially
curating the legacy. He knows what Big L meant
to the culture, and he's stepping in to make
sure it's handled properly. And then on April
17, 2025, the Coleman family officially confirmed
a final, definitive album was on the way. It's
titled Harlem's Finest, Return of the King. And
it was released on Halloween, October 31, 2025.
Halloween. That seems very fitting for the guy
who famously wrote Devil's Son. Very fitting.
But it hasn't been a completely smooth rollout.
The family also released a statement explaining
why a lot of Big L's older songs have been removed
from streaming services recently. Why is that
happening? It's the legal nightmare of 90s hip
hop preservation. Uncleared samples, uncredited
producers. The music was made in a time when
you could just grab a piece of a James Brown
record and loop it. Now, decades later, lawyers
get involved and things get pulled down. So the
legacy is literally fighting to stay audible
in the digital age. It is. But the fact that
we are getting a new, officially sanctioned album
in 2025 shows just how hungry the culture still
is for his voice. His influence hasn't faded.
And there was supposed to be a documentary, too,
right? For years, we've heard about Street Struck.
Yeah, Street Struck, the Big L story. It was
being directed by a childhood friend, a guy named
Juz. They announced it way back in 2017, and
a trailer was released even earlier in 2009.
But as of 2024, it was still unreleased. It's
become one of those lost artifacts of hip -hop
history. Hopefully, with the momentum from the
2025 album, that project finally sees the light
of day. Because people need to see the footage.
They need to see him rapping in the park as a
teenager to really get it. Absolutely. Because
when you see him, you realize his peers weren't
lying or exaggerating about his skill. The legendary
DJ Funkmaster Flex went on record in 2019 saying
that Big L was a better lyricist than the notorious
B .I .G. and Jay -Z. That is an incredibly bold
statement. In New York City, that's almost blasphemy.
It is. But he said, I know people will get mad
at me. But it's the truth. And another elite
lyricist, Royce Day, 5 '9", said he believed
L would be a consensus top three rapper of all
time if he had lived. And the streets that raised
him, they honored him too. In 2022, they officially
renamed the corner of 140th and Lenox. Lamont
Big L Coleman Way. He is literally a part of
the map of Harlem now. You can't drive through
that neighborhood without seeing his name. So
let's zoom out. We have a guy who died tragically
young, left behind a relatively small body of
official work, but cast this absolutely giant
shadow over the genre. What does it all mean?
What is his ultimate legacy? I think Big L represents
the ultimate pure MC because he didn't live long
enough to make a bad album. He didn't live long
enough to sell out. He didn't do. quirky, awkward
collaboration with the pop star that aged poorly.
He is frozen in amber at the peak of his power.
He is. He is frozen as this hungry, impossibly
talented phenomenon. In our collective memory,
he will always be the best rapper in the room,
the undefeated battle champion. But the tragedy
is that he was just about to step out of that
room and onto the world stage. He was leaving
the local gym to go play in the NBA finals. And
that leads directly to the provocative question
I want to leave our listeners with. It's the
Game of Thrones question of him. All right, let's
hear it. If Big L signs that Rockefeller deal,
if he survives February 15th, 1999, how does
the entire landscape of 2000s hip hop change?
Does Jay -Z still become the singular, untouchable
billionaire mogul if he has to share the spotlight
and the label's resources with a lyricist of
Big L's caliber? Does Big L become the undisputed
face of New York rap? Or do they become the greatest
duo in hip -hop history and push each other to
even greater heights? Or, on the flip side, do
their massive talents and egos clash and burn
the whole empire down? We will never, ever know.
And that unsolvable mystery is a huge part of
the legend. A legend that as of October 2025
is still being written. Indeed. Still being written.
Thanks for taking this deep dive with us. If
you haven't, please go check out Lifestyles of
Dapor and Dangerous. Go listen to Eubonics and
just appreciate the skill of a true master of
the craft. And pay attention to the lyrics. You
might need to rewind a few times to catch everything.
Always. We'll catch you on the next one. Stay
curious.