Welcome to the Deep Dive. We're here, as always,
to take that big stack of research, all those
articles and notes you've got, and boil it all
down to the essentials, the stuff you really
need to know. And today, we've got a big one,
a really big one. We're diving deep into the
career of O'Shea Jackson Sr. You know him, of
course, as Ice Cube. Yeah, decades long, incredibly
complex career. Sometimes feel like he's lived
multiple lives, honestly. It's kind of wild when
you think about it. I mean, who else has a trajectory
quite like his? It's so radical, but also incredibly
successful. Right. You look at his influence,
and it's not just that he was part of cultural
shifts. He was often driving them. We're talking
about someone who basically helped build gangster
rap. The architect, you might say. Exactly. Then
became this... really fierce political voice,
then somehow pivots into being a major Hollywood
star, like bankable family comedies and stuff.
And then starts a whole professional sports league.
It's a lot. It really is. That transition alone
could be its own deep dive. For sure. So our
mission today for you listening is to try and
get a handle on these key periods of his influence
quickly but thoroughly. We need to map out how
his public image, his persona evolved. Yeah,
from those explosive, really controversial beginnings
with N .W .A. through that peak political commentary
period and then right into this transformation.
Global actor, producer, entrepreneur. OK, so
let's start with the basics. Just a snapshot.
Born O'Shea Jackson, June 15th, 1969 in L .A.
Right. And he's a rapper, songwriter, actor,
film producer, a true multi hyphenate. His importance.
Well, you see it solidified with things like
the 2016 Rock and Roll Hall of Fame induction
for N .W .A. And just recently, right, N .W .A.
got the Grammy Lifetime Achievement Award in
2024. That's it. So this isn't just some flash
in the pan celebrity. He's foundational. An institution,
really. Okay, so to really get that early fire,
the revolutionary stuff in his music, we kind
of have to look beyond just the NWA legend, right?
Understand where he came from, his upbringing,
and maybe crucially, his discipline. Yeah, he
grew up in South Los Angeles, the Westmont section
specifically. Definitely a high crime area back
then. But his family background is interesting.
It wasn't maybe the stereotypical story you'd
expect. Not entirely. His parents had this working
class foundation, you know, focused on stability.
His mom was a hospital clerk and custodian. His
dad worked two jobs, machinist and a groundskeeper
at UCLA. That background feels important. It's
not like immediate dire poverty, maybe, but it's
about hard work, seeing the system up close,
observing inequality. You can feel that fueling
the early lyrics. Absolutely. And he started
writing really young, like ninth grade in high
school, George Washington Prep. Apparently he
took up the challenge in a typewriting class.
Really? Typewriting? Yeah. He actually said the
rhythm of the keyboard clicks helped him figure
out the rhythms for his raps. Kind of cool. Huh.
Okay. And what about the name, Ice Cube? Where
did that come from? It's pretty iconic. It's
actually one of the funniest stories in the source
material, I think. Yeah. Came from his older
brother. No. Yeah, apparently his brother got
fed up with him one day and threatened to, quote,
slam him into a freezer and pull him out when
he was an ice cube. Just like that. Sibling rivalry.
Pretty much. A playful start for a name that
ended up meaning something so hardcore, you know.
Definitely. Okay, here's the part that really
jumps out. The thing that kind of flips the script
on that young, revolutionary NWA image. Ice Cube
wasn't just about the music. He was, well, he
was practical. Incredibly pragmatic, yeah. This
is key. He seriously considered architectural
drafting as his backup plan. His real career
path if music didn't work out. A backup plan,
wow. And he actually pursued it. Oh, yeah. He
went to Taft High School for it, which meant
taking like a 40 mile bus ride each way every
day out to the suburbs. Yeah. Woodland Hills.
That's dedication. 40 miles daily. Yeah. Away
from South Central. And it wasn't just talk.
He got a diploma in architectural drafting from
the Phoenix Institute of Technology in 1988.
So he was actually a certified draftsman. That
implies like precision, planning. Seeing the
big picture, blueprinting things, does that track
with his lyrics, you think, that structure? I
think it absolutely does. That ability to see
a structure, plan it out. Build it piece by piece.
That defines his whole career, not just the music.
You see it in how dense his verses are, how he
structures arguments. And later on, we'll see
it in his albums, too, right? The thematic structure.
Exactly. Like with Death Certificate. The planning
is meticulous. So, yeah, the revolutionary fire
was there, but it was being channeled by someone
who knew how to draw up a plan. OK, but the music
bug bit hard and early. 1986, he's only 16, forms
a group, CIA. Yeah, with his friend Sue Jenks.
They started performing at parties, parties hosted
by Dr. Dre. Ah, the connection. Right there.
Immediate. And Dre recognized Cube's writing
talent straight away. Cube actually did some
ghostwriting for Dre's earlier group, World Class
Wrecking Crew, helped write their hit Cabbage
Patch. So he was already writing hits, basically.
Pretty much. But the real start of N .W .A.,
The Catalyst, was when he sold his first song
to Eric Wright, Yeezy E. And that sale, that
track, brought the core group together and basically
launched gangster rap as we know it. That's the
story. And here's a little detail people sometimes
miss. Cube was the only main N .W .A. guy not
actually born in Compton. He was from South Central
L .A. Gives him slightly different lens, maybe.
Interesting. So you had Cube, the writer, Dre,
the producer. What was that dynamic like? Electric,
by all accounts. Cube wrote Boys in the Hood,
Eazy rapped it, and boom. That defined the narrative.
But what's really crucial about this era is just
how central Cube was as the writer. He wasn't
just a rapper in the group. No, he was the lead
rapper. And he wrote most of the lyrics on Straight
Outta Compton, that iconic 1989 album. Wow. Most
of it. That album was a cultural earthquake.
It basically defined West Coast hip -hop's identity.
Controversial, violent, but undeniable. He was
the voice, the pen, the architect, like you said.
Which makes the breakup, what happened next,
even more dramatic. It all came down to money,
didn't it? And respect. Yeah. Late 1989, Cube
starts asking questions. Questions about his
pay, about how the group's manager, Jerry Heller,
was handling things. And the number that gets
thrown around in the sources, it's kind of shocking.
It's staggering. He reportedly got paid only
$32 ,000. $32 ,000. For writing most of Straight
Outta Compton A &E, most of Eazy -E's huge debut
album, Eazy Does It. That's the reported figure,
$32 ,000 for helping build an empire that was
making millions. That's, yeah, that's grounds
for war right there. It was pure exploitation,
basically. Especially when you consider the profits
Ruthless Records was making. And the sources
say the final straw was the contract they eventually
offered him. It didn't even properly list him
as an official member of NWA. Seriously, after
writing all those lyrics. Treated him like a
hired gun, not a partner. So that disrespect,
financially and personally, that was it. He walks,
late 89, sues Heller, settles out of court, and
then the disses start flying. Oh yeah. And W
.A. did not take it well. They went after him
hard on their next EP, 100 Miles and Runnin',
and then again on the final album, Niggas for
Life. Vicious stuff. So that sets the stage,
right? This intense personal anger mixed with
the political fire he already had. He's got to
reinvent himself. Solo. And he does it immediately.
Walks away from the biggest rap group on the
planet, facing lawsuits, getting dissed. And
what does he do? Drops his solo debut, America's
Most Wanted, in 1990. But not from L .A., right?
He switched coasts. Yeah, that's a really smart
move. He goes to New York, works with Public
Enemy's production team, the Bomb Squad, legendary
producers. Why was that so strategic? Well, it's
a deliberate step away from that West Coast G
-funk sound Dre was starting to perfect. Working
with the Bomb Squad meant blending his West Coast
reality rap with that dense, noisy, politically
charged East Coast sound. And it worked. Instantly.
Huge hit. It submitted his stance, you know,
black nationalism, the struggle. But... It also
immediately drew fire. Accusations of misogyny,
racism. Right off the bat. So the controversy
followed him, or maybe he courted it. A bit of
both, probably. But even while he's building
this solo icon status, he's also, like, putting
his money where his mouth is. Community building.
How so? He used his platform to help other artists.
Most notably, the female rapper Yo -Yo, who was
on his first album. He made her the head of his
record label, Street Knowledge. Producer debut
album. So he wasn't just tearing things down.
He was trying to build something, too. Exactly.
Show he was thinking bigger than just himself
and commercially. He proved he could do it alone
fast. Released the Kill It Will EP later in 1990.
Became the first rap EP ever to go platinum.
Platinum EP. He was undeniably the hottest rapper
out there. No question. Which brings us to 1991.
His second album, Death Certificate. And if America's
Most Wanted stirred things up. Death Certificate
was throwing dynamite. Pretty much. An outright
declaration of war, politically and personally.
And here's that architectural planning again,
right? The structure of the album? Particulous.
It wasn't just a collection of songs. It was
split. The death side and the life side. What
was the idea behind that? The death side was,
in his words, a vision of where we are today.
bleak, unflinching look at society, systemic
problems. The life side was a vision of where
we need to go, a call to action, self -improvement
based on those black nationalist ideas. But that
structure really does reflect that draftsman's
mindset, blueprinting the message. Totally. But
the content, even more controversial than the
first album. Accusations flying, anti -white,
anti -Semitic, intensely misogynistic. The tension
between the message and the language was just...
Right there. Unavoidable. Which means we have
to talk about no Vaseline. You have to. This
is his final, brutal answer to NWA's disses.
And it went nuclear, attacked his old crew, but
especially Jerry Heller. Viciously. The source
material is very specific about the language
used. It targeted Heller, referencing his Jewish
ethnicity with terms like white Jew, white man,
devil, and it directly called for his murder.
Yeah, that's incredibly dark, even for a rap
beef. Crossed a serious line. The backlash was
immediate and huge, obviously. But for full context,
the sources also note that much later, in 2015,
Cube did express regret. specifically about using
the word Jew, said his target was Heller personally
and financially, not the whole community. OK,
that context is important, even if it came years
later. There was another track on there, too,
right? Black Korea. Right. Focused on the tensions
between black residents and Korean store owners
in South Central L .A., called racist at the
time. But looking back, it felt prophetic, eerily
so. It basically laid out the tensions that exploded
in the 1992 L .A. riots. Just months after the
album dropped. Wow. So this political firestorm
leads him right into his biggest commercial success.
Exactly. The Predator, released in 1992 right
after the riots. Steeped in that chaos. And commercially,
this was the peak. Over 3 million copies sold
in the U .S. And here's the crazy stat. The Predator
was the first album ever to debut at number one
on both the R &B hip -hop charts and the main
pop charts. Simultaneously. First ever. That's
huge crossover appeal. Without softening the
message, it seems. Not really. The song Wicked
directly referenced the riots. April 29 was Power
to the People, and we might just see a sequel.
Capture that raw attention. And this album gave
us massive hits like It Was a Good Day. A classic.
Showed a different side, too. Yeah. Calmer, more
narrative, and also Check Yourself, which was
more aggressive. cemented his superstardom okay
but here's the massive twist the paradox he hits
this incredible peak number one debut millions
sold but the sources are really clear on this
yeah his original core rap audience the political
heads, they started falling off. The sources
say his rap audience severely diminished and
never regained the prominence of his first three
albums. So his biggest commercial success marks
the point where his original fan base starts
to drift away. Essentially, yes. That's a huge
turning point. It forces him to rethink things.
The political edge maybe got too sharp for some,
or the market just moved on to the next thing
G -Funk was exploding then. So the artist, the
draftsman, had to adapt or fade away. And Ice
Cube chose adaptation, big time. And that adaptation
came fast, mainly through movies. His first big
role, 1991, Boys in the Hood, playing Doughboy.
Directed by John Singleton. Seminal film. And
the irony, of course, is the title comes from
that first NWA song Cube wrote. He was so convincing
in that role, just embodied that character caught
in the system that gave him instant acting cred.
Absolutely. But you see his priorities shifting.
Almost immediately. He actually turned down a
big role after that, supposed to co -star with
Janet Jackson in Singleton's next movie, Poetic
Justice. Really? Who ended up getting that role?
Tupac Shakur. And it was a huge boost for Tupac's
acting career. So, cute passing on that says
something. Maybe moving away from those intense,
dramatic roles. Or wanting more control. Could
be. Or just wanting a different image. Musically,
though, he did try to follow the trend for a
bit. His 1993 album, Legal Injection. Right.
That one leaned heavily into the G -Funk sound
Dre was killing it with. Exactly. And that's
kind of why it didn't fully connect with his
old audience or the critics he was following,
not leading, which wasn't his usual style. So
the reception was kind of lukewarm. Yeah. I mean,
it had hits like Bop Gun, One Nation, and you
know how we do it, big singles. Yeah. But the
sources say after this album, that core sociopolitical
rap audience. Pretty much gone. He wasn't that
voice anymore. But old wounds started to heal
a little. He worked with Dre again. Yeah, 1984.
First time since the NWA split. Yeah. They did
the track Natural Born Collaz. Signaled that
maybe that huge public beef was cooling down.
Opened the door for more later. Okay, so while
his solo music thing is shifting, he's also dealing
with the whole East Coast, West Coast rap booth,
right? That was heating up in the mid -90s. Fiercely.
And there's this feeling on the West Coast, rightly
or wrongly, that the East Coast media, the magazines,
the radio, they were ignoring or downplaying
West Coast artists. So Cube decides to address
this head -on. Strategically. Forms a supergroup,
almost. West Side Connection, in 1995, with MAC
-10 and WEC. And the goal was explicit. Purely
ideological, really. To wave the West Coast flag,
challenge that perceived East Coast bias, reinforce
West Coast pride. How'd that go? Their first
album, Bow Down, in 96. It was basically a declaration
of war. Lyrically, very unapologetic. And it
worked, commercially at least. Went platinum
pretty quickly. Showed he could still mobilize
that regional pride, even if the political audience
had shrunk. But the group didn't last forever.
Nah, they disbanded around 2005. And the reason
why tells you everything about Cube's focus by
then. There was a falling out between Cube and
MAC -10. Over what? According to the sources,
it was because Cube's Hollywood commitments were
getting in the way of the group touring properly.
Film had clearly become the priority over music
group commitments. Which brings us right to that
Hollywood transformation. It really kicked off
with advice from John Singleton. Yeah, Singleton
apparently told him, if you can write a record,
you can write a movie. Simple as that. And Cube
ran with it. Co -wrote and starred in Friday
in 1995 with Chris Tucker. That movie was the
pivot point. Financially, huge success. Made
for like $3 .5 million, grossed over $28 million
worldwide. Pina's budget, big return. But it
was more than just the money, right? The image
shift. Totally. The sources say it critically
reshaped his public image into an actor. He went
from Doughboy, that intense, tragic figure, to
Craig in Friday. Laid back, funny, relatable.
That gave him huge mainstream flexibility. And
he started directing, too. Yep. Made his directorial
debut in 1998 with The Players Club. His film
career just exploded after that. He wasn't just
doing comedies, either. No, showed range. Like
three kings in 1999 that acclaimed war comedy
with George Clooney and Mark Wahlberg. But his
real genius was launching franchises, barbershop,
and the family -friendly stuff from there yet
broadened his audience massively. So during this
whole Hollywood boom, what was happening with
his music? Was it just on the back burner? Not
entirely, but it felt more like checking in,
reminding people of his roots. His albums Warm,
Peaceful, Hear One and Two came out then, and
they featured reunions with Dre and MC Ren, slowly
patching up those NWA relationships on record.
And he was doing some interesting collaborations
outside of hip -hop, too. Yeah, really smart
strategic moves to broaden his reach even further.
He worked with David Bowie and Trent Reznor on
a remix of Bowie's track I'm Afraid of Americans
in 97. Bowie and Pube, wow. And then, crucially,
he featured on a track with the new metal band
Korn. Children of the Korn, in 98, and even joined
them on the Family Values tour. Why Korn? That
seems like an odd fit. Genius move, though. It
put him right in front of that whole alternative
rock, new metal crowd, an audience that was already
into controversial figures, outsider vibes, expanded
his base way beyond hip -hop, which had kind
of moved on from his early sound anyway. Smart.
And then he cemented that elder statesman role
with that big tour in 2000. The Up in Smoke tour.
Massive. Him, Dre, Eminem, Snoop Dogg. Basically,
the Kings of West Coast rap plus Eminem. Huge
statement. So by the time his 2006 album, Laugh
Now, Cry Later, comes out, the music is kind
of riding the wave of his movie fame. Largely,
yeah. It still did well. Sold like $144 ,000
first week. Had the single Why We Thugs. Proved
people still listened when he dropped music,
even if film was clearly the main focus. Okay,
so post -2006, Cube is firmly this. This mogul,
right? Producer, entrepreneur. But the music
doesn't completely starve him. No, it remains
like a personal anchor for him, it seems. He
keeps collaborating, often across different styles.
Worked with crunk guys like Lojan and the Eastside
Boys. Did tracks with Insane Clown Posse, Tech
N9. Keeps his hand in, stays connected. But releasing
his own albums? That got tricky. Lots of delays.
Yeah, his business interests, the film schedules,
they clearly took precedence. His 10th album,
Everything's Corrupt, that was a prime example.
Announced way early, so it's supposed to have
a title track timed for an election. For the
political heads, he said. Right. But it kept
getting pushed back. Finally came out in 2018.
Took years. The film slate just seemed to dominate.
But that West Coast connection, that loyalty,
that stays strong. He formed another super group
recently. Yeah, Mount Westmore. In 2020, him,
Snoop Dogg, E -40, Too Short, Absolute Legends,
Titans of the West Coast, released their debut
in 2020. Except they're dropping music now. actively
11th album man down just came out in november
2024 and a 12th man up this is apparently scheduled
for 2025 he even put out a single called before
hip -hop so the music drive is still there okay
shifting back to the producer director hat he
explored some interesting themes there too beyond
just entertainment that documentary series black
white back in 2005 co -created that explored
race and identity by having families basically
swap racial appearances. Provocative stuff. And
he directed that ESPN documentary, too, The 30
for 30. Straight out of L .A. in 2010. That's
a fantastic piece of work. It digs into how L
.A. politics, hip -hop, and the Raiders football
team all got tangled up together in the late
80s, early 90s. His connection to the Raiders
is deep, isn't it? Yeah, N .W .A. adopting that
silver and black Raiders gear. That basically
made the team's image. synonymous with hip -hop
rebellion he's a diehard fan still is even now
they're in vegas released two raiders anthems
over the years loves the dodgers and lakers too
true la guy and the movie franchises kept rolling
turning into tv shows even all right are we there
yet Became a TV series on TBS in 2010. Huge success.
Got renewed for like 90 episodes. Shows his knack
for building bankable properties. And then the
big one, bringing his own story full circle,
Straight Outta Compton, the movie, in 2015. He
was an executive producer on that and made sure
the story got told from their perspective. That's
a pretty amazing moment, seeing your story pass
down like that and being involved in telling
it. Now, we talked about him walking away from
NWA over principles, over money. Does that uncompromising
streak still show up even now? He's a multimillionaire
modal? Absolutely. Perfect example. 2021. He
was set to star in a big comedy. Oh, hell no.
It's called Stepdude Now with Jack Black. Major
movie. What happened? He left the project. Walked
away because he refused to get the COVID -19
vaccine, which the production required. And that
cost him? Reportedly, a $9 million paycheck.
Just gone. $9 million. Yeah. So whatever your
views on that specific issue, it shows he's still
willing to stick to his guns, prioritize his
personal stance over a massive payday. That core
cube, the guy who fought ruthless records. Right.
Still there. And then the most unexpected venture,
maybe? Sports ownership? Big three. Yeah. Launched
in 2017, professional three -on -three basketball
league with former NBA stars. This isn't just
like a celebrity vanity project. No, it's legit.
A successful growing league. Positions him as
a serious sports entrepreneur, leveraging his
fame, sure, but also his business sense. It's
that draftsman again, right? Yeah. Building another
solid structure. Okay, let's move into the more
personal side. Behind the mogul, the rapper,
the actor, what do the sources say about his
personal life, his beliefs? Well, stability seems
key in his family life. He married Kimberly Woodruff
way back in 1992. Still together, over 30 years,
they have four kids. He became a grandfather
in 2017. That's a long time in any world, let
alone entertainment. And how did he approach
raising kids, given the content of his early
music? That's interesting. Back in 2005, he apparently
said he made a point of teaching his kids to
question the violence they see in all media.
Not just rap lyrics, but... Movies, TV, everything.
So positioning himself as a media critic, not
just a creator of it. Kind of, yeah. A critical
perspective on normalization. Now, his religious
path, that's more complex, not straightforward.
He converted to Islam. Yes, back in 1990. got
introduced to the Nation of Islam, the NOI, through
his connections with Public Enemy. Now, he denies
being like an official card -carrying member
of the NOI, but he definitely adopted their core
ideology of black nationalism. You hear it all
over his early solo stuff. But he doesn't strictly
follow one doctrine. He describes himself as
a natural Muslim. Says he listens to his own
conscience because ultimately it's just him and
God. Very individualistic approach. And he's
made comments suggesting a broader view, too.
Yeah. In 2017, he said something like he thinks
religion is stupid, partly, but then clarified,
saying he's on the Islam tip, but also the Christian
tip and the Buddhist tip kind of takes elements
from different places. And he came out in support
of same -sex marriage back in 2012. So definitely
not adhering to a rigid dogma. OK. This complexity,
though, it sits alongside probably the most persistent
criticism he's faced throughout his career. The
accusations of anti -Semitism, promoting conspiracy
theories. We need to unpack this carefully, just
reporting what the sources say. Right. Impartially.
The first major incident mentioned goes back
to 1991, around the release of death certificate.
At a press conference, he publicly endorsed a
Nation of Islam book called The Secret Relationship
Between Blacks and Jews. And that book makes
false claims. Yes, it falsely claims that European
Jews played a dominant role in the Atlantic slave
trade. endorsing that book put him right in the
middle of a huge controversy. Then there's the
No Vaseline track, which we talked about, the
specific language used against Jerry Heller.
Yeah, the sources highlight the use of terms
like white man, Jew, white Jew, devil, directed
at Heller, alongside the call for violence. That
language was and is seen as anti -Semitic. And
this issue didn't just stay in the 90s. It came
back more recently. Sharply. In 2020, he got
a lot of criticism for a series of posts on Twitter
over a single day. He promoted Louis Farrakhan,
the NOI leader, and shared various images and
memes linked to what sources describe as disproven
anti -Semitic conspiracy theories. So the same
themes resurfacing decades later on a huge public
platform. Exactly. Which shows those early ideological
leanings were still present, still being expressed
publicly. OK, so how has he responded to these
accusations over the years? It's important to
include his side as a. His defense has been pretty
consistent. Back in 2008, he argued he was too
busy being pro -black to be anti -anybody. That's
been a recurring theme. And on No Vaseline. As
we mentioned, that 2015 statement where he regretted
the specific word Jew, insisting his attack was
solely on Heller personally and financially.
And the 2020 Twitter stuff. His response then
was more dismissive of the criticism, called
it the hype. So he was just telling his truth.
So we report. The incidents, the content, the
criticism and his consistent defense. Just laying
out what the sources present. Hashtag tag outro.
All right. So we've traced this incredible arc
decades of Ice Cube. And the picture that emerges
is just full of. Well, contradictions, but also
brilliant, brilliant adaptation. Definitely.
On one hand, you've got that raw, uncompromising
political voice, the guy who defined early gangster
raps, power and controversy. That legacy is solid
Rock and Roll Hall of Fame, Grammy Lifetime Achievement
for N .W .A. But then there's the other side.
The incredibly pragmatic businessman, the entertainer
who crossed every genre line imaginable, used
his fame to pivot when his music audience shifted,
and built this massive film and TV empire. Got
his star on the Hollywood Walk of Fame in 2017.
Yeah, Bad Journey. From Doughboy's Tragic Reality
to Nick Person's Family Avengers and Are We There
Yet? From being an actual draftsman to founding
the Big Three League. It's like a masterclass
in American enterprise. Turning rebellion into
a brand. It really is the ultimate story of turning
revolutionary art into durable commerce. Which
brings us back to that paradox we hit on earlier.
Right. The sources clearly state his core political
rap audience feeded after the Predator in 92,
right when his commercial music success peaked.
But his film career exploded right after that.
So it leaves us with a big question, really.
Something for you to think about. Does building
that kind of massive, mainstream, commercially
safe empire... Does it always mean you have to
sand down those revolutionary edges, the very
things that got you noticed in the first place?
And maybe is that shift from writing about systemic
injustice on the streets for like thirty two
thousand dollars to producing family comedies
and running sports leagues for millions? Is that
the ultimate definition of American success,
regardless of what might get lost creatively
along the way? Something that you want. Definitely.
Thanks for diving deep with us today. We'll catch
you on the next deep dive.