Welcome back to the Deep Dive. Today we are really
getting into it with a massive figure, William
Bradley Pitt. I mean, this is someone who's more
than just an actor, right? He sort of embodies
the whole modern celebrity package. Absolutely.
Actor, producer, activist, public figure. He's
the definition of a multi -hyphenate. And when
you look at the sheer volume of sources, biographical
stuff, career data, it's huge. Our goal today
is really to, you know... Sift through all that.
Find the surprising bits that overlooked things.
Exactly. Cut through the noise, the gossip, and
figure out what really made his career tick over
these, what, three decades plus? And the scale
is just, it's hard to wrap your head around sometimes.
It really is. I mean, the films he's been in
have grossed, what is it now, over $9 .3 billion
worldwide? That's staggering. But it's not just
the money, is it? He was initially seen as, well,
a sex symbol. Right, but... The awards tell a
different story about his depth. Two Academy
Awards, one for acting, one producing two Golden
Globes, even two Primetime Emmys. That shows
real creative staying power. Plus, you can't
ignore the People's Sexiest Man Alive thing.
Twice. 1995 and 2000. It's part of the package,
sure. But think about the journey. This Midwestern
kid who famously drops out of the University
of Missouri just two weeks before he's supposed
to graduate. That's the story everyone knows,
isn't it? That leap. Yeah, and it's kind of key
to understanding him, I think. That willingness
to ditch the safe path because, as he put it,
films weren't made in Missouri. So he had to
go where they were made. And it's fascinating
who he looked up to back then. Oh yeah, his early
heroes. Gary Oldman, Sean Penn, Mickey Rourke.
That's not the list you'd expect from someone
who became a heartthrob, is it? Not at all. It
signals something different. Intensity, grit,
maybe a bit of danger. He wasn't just aiming
for handsome leading man roles, clearly. That
desire for challenging stuff was baked in early.
Okay, so let's lay the groundwork. William Bradley
Pitt, born in Shawnee, Oklahoma, 1963. But he
grew up in Springfield, Missouri. Right. The
sources call it Mark Twain country, Jesse James
country. Gives it a certain flavor, doesn't it?
It does. And the family setup sounds pretty solid,
pretty middle American. His dad, William Alvin
Pitt, owned a trucking company. His mom, Jane
Etta, was a school counselor. And he had younger
siblings, Doug and Julie Neal. And it was a structured
upbringing in other ways, too. Raised Southern
Baptist, conservative Christian household. That
context is really important for understanding
his later path. How so? Well, the sources are
clear about his later journey away from that.
He sort of bounced between agnosticism and atheism
for a while before eventually kind of finding
his own sense of spirituality later on. So moving
from that inherited structure towards something
more personal, more questioning. Exactly. Yeah.
And you see that questioning, that restlessness
pop up again and again in his choices, both in
his career and personal life. A real deep curiosity
seems to drive him. You could even see hints
of it in high school, maybe. At Kickapoo High.
Yeah, I mean, look at his activities. He wasn't
just doing sports golf, swimming, tennis, which
he did, but he was also in Key Club, forensics,
you know, competitive speaking, and musicals.
So the performance bug was there early, even
if acting wasn't the obvious path yet. Definitely.
Which leads us to that famous decision at the
University of Missouri. He started there in 82,
majoring in journal of him, focused on advertising.
Sensible choice, practical, probably made his
parents happy. You'd think so. But it wasn't
enough for him. He loved movies. He called them
a portal into different worlds. It wasn't just
entertainment. It was something deeper. And he
realized, well, you don't make movies in Missouri.
Pretty much. So two weeks before getting his
degree, he just left. Packed up, headed for L
.A. It's that classic Hollywood gamble. Abandoning
the sure thing for the long shot must have seemed
crazy to people back home. Oh, I bet. It's the
kind of move that ends in tears or... Well, creates
Brad Pitt. So he gets to L .A., starts taking
acting lessons studied with Roy London, a really
respected coach. And then the grind begins. Yep.
Odd jobs trying to get noticed. He did the uncredited
bit parts in 87. No way out. No man's land. Less
than zero. Tiny stuff. TV was where he started
getting actual screen time, though. Yeah, paid
his dues there. Soap opera debuts on Another
World, guest spots on shows like Trial and Error,
Growing Pains. You know, standard stuff for a
young actor finding his feet. Wasn't he on Dallas
for a bit? He was. Recurring role. 87 to 88,
played Randy, the boyfriend of Charlotte Wade,
Jenna Wade's daughter. That was probably crucial
for her income and just being on a big set regularly.
Now, here's something most people probably don't
know. His first actual leading role in a movie.
Ah, yes. The Dark Side of the Sun. Made in 1988,
he plays this young American guy in Yugoslavia
looking for a cure for a skin condition. But
nobody saw it for ages, right? Exactly. The Croatian
War of Independence broke out, and the film just
got shelved. It didn't come out until 1997. Imagine
thinking you've got your big break, and then
it just vanishes because of a war. Back to square
one, basically. Tough break. So if Dark Side
of the Sun got buried, the real launchpad, the
moment everyone remembers, has to be 1991, Thelma
and Louise. Oh, absolutely. Ridley Scott directing,
Pitt plays J .D., the hitchhiker, and bam, instant
global sex symbol. It was that scene, wasn't
it, with Geena Davis? Totally. That's the scene
everyone points to. It just cemented that image,
charming, a little dangerous, impossibly good
-looking. You went from that guy from Dallas'
to Brad Pitt almost overnight. But navigating
that sudden fame... It wasn't smooth sailing
immediately after, was it? No, it's tricky. He
did a couple of films right after, trying to
capitalize but maybe also find something interesting.
Johnny Suede, this low -budget indie about a
rock star, and Cool World, that weird animation
live -action mix. And they didn't really land.
No, both pretty much bombed, critically and commercially.
It's like, okay, the world knows he's a star,
but the industry wasn't quite sure what to do
with him yet, beyond the looks. A bit of a post
-breakthrough wobble. Which makes 1992 even more
important. A river runs through it. Huge turning
point. Directed by Robert Redford, which instantly
gives it prestige. And the critics really took
notice. People magazine literally said it proved
he was more than a cowboy had at hunk. So this
was him proving his acting chops. Well, yes,
in the eyes of the public and critics. But here's
where it gets really interesting, digging into
his mindset. Pitt himself looked back on that
performance later. and was incredibly hard on
himself. Really? The one that made people take
him seriously? Yeah. He called it one of his
weakest performances. Said he felt overwhelmed
by it. Wow. That's quite self -critical. It is.
But his reasoning is fascinating. He said he
benefited hugely from the talent around him,
the director, the cast. He used this analogy,
like playing tennis with a better player, your
own game automatically improves. So he learned
the value of the team. Not just his own role.
Exactly. Surround yourself with the best. Choose
projects based on the whole package, not just
the star part. You can see the seeds of Plan
B right there, that philosophy. Makes sense.
And after that realization, he seemed to actively
seek out roles that messed with the pretty boy
image. Totally. Look at California in 1993. He
reunited with Juliette Lewis, but this time he's
playing Early Grace, this terrifying, unpredictable
serial killer. And people were impressed by the
transformation. Oh, yeah. Rolling Stone said
he had that boyish charm, but could switch to
pure menace with just a snort. It showed real
range. And don't forget his little role in True
Romance that same year Floyd, the stoner roommate.
Hilarious. That range got him noticed by the
industry too, right? Yep. He won the Showist
Award for Male Star of Tomorrow in 93. Things
were definitely lining up for him to become a
major leading man. But even then... There were
bumps. Like Interview with the Vampire in 94.
Huge film. Massive cast crews. Dunst. Banderas.
Right. But his performances as Louis didn't get
great reviews. Some critics were pretty brutal,
actually. One said he conveyed zero inner torment.
A reminder that even big stars in big movies
can misfire sometimes. But he bounced back fast.
Legends of the Fall later that same year. Yeah,
that was much better for him. Got his first Golden
Globe nomination for Best Actor. The film itself
got mixed reviews, but his performance as Tristan
Ludlow was widely praised. It really solidified
him as a proper leading man. And then 1995 feels
like the year it all clicked into place, critically
and commercially. Definitely. He went after the
role in David Fincher's Seven. playing the detective
opposite Morgan Freeman. He specifically said
he wanted it to get away from the pretty boy
thing, to play someone flawed. He actively chose
darkness. And it worked, big time. Critics liked
him in it. Variety called his work determined,
energetic, creditable. And the movie was huge,
over $320 million worldwide. He was now bankable
and respected. But the real peak of that mid-'90s
run, for me, has to be 12 Monkeys. Terry Gilliam.
Playing Jeffrey Goins, that totally unhinged
anarchist character. Manic is the word. It was
such a go -for -broke performance, and it paid
off. Yeah. Won the Golden Globe, got his first
Oscar nomination, Best Supporting Actor. You
just couldn't ignore him in that role. No way.
Critics talked about his startlingly frenzied
performance, his weird magnetism. That was the
moment, I think, where the box office appeal
from Thelma and Louise finally merged completely,
with the serious critical respect he'd been building
towards. He wasn't just a movie star. He was
a serious actor. So he's established as this
serious star. The next big evolution is moving
into that power broker role. And that really
comes down to Plan B Entertainment. Which he
co -founded in 2001, right? With Jennifer Aniston
and Brad Gray. That's the one. And Plan B is,
well... It's more than just a shingle. It became
his way to really control his creative destiny
and maybe more importantly to champion the kinds
of films that maybe wouldn't get made otherwise.
Difficult films. Riskier material. Exactly. Think
about it. The Big Short, a complex film about
the financial crisis. War Machine, a tricky war
satire. The Tree of Life, a poetic, almost experimental
Terrence Malick film. These aren't easy sells
for major studios unless someone like Pitt is
pushing for them. And using his clout to get
them made. Precisely. It's about backing visionaries,
backing tough subjects. And the track record
is just incredible. As a producer, he's got three
Best Picture Oscar nominations and that big win.
The win was for 12 Years a Slave in 2013. Right.
Which was just a monumental film. Yeah. Tackling
American slavery head on, unvarnished. Plan B
didn't just produce it. They championed it. Got
it seen. Pitt put his name and weight behind
something incredibly difficult and important.
That says a lot about his priorities as a producer.
And the other nominations were Moneyball and
The Big Short. But what about The Departed? That
won Best Picture in 2006 and Plan B produced
it. Ah, yeah, that's an interesting one. He was
credited as a producer on screen. But the Academy
has specific rules about who gets the actual
statuette. In that case, only Graham King was
deemed eligible for the Oscar itself. But still,
being involved in a Best Picture winner that
early showed their ambition. What strikes me
about Plan B is the range. They did Troy in 2004,
this huge historical epic. Yeah, their first
big production. But then they also do these really
sensitive, artful dramas like... The assassination
of Jesse James by the coward Robert Ford or Malick's
Tree of Life, which even won the Palme d 'Or
at Cannes. It's an amazing balancing act, isn't
it? They can make a massive zombie movie like
World War Z. Which made a fortune. Right. And
then use that success, presumably, to help finance
these prestigious, maybe less commercially obvious
films like Moonlight or Minari, both of which
won Oscars in critical adoration. They even backed
Beetlejuice recently. They've really mastered
that model using blockbusters to fund the arthouse
passion projects, and they moved into TV too.
Briefly, yeah. They had a joint venture with
ABC Studios for a sci -fi show called Resurrection
for a couple of seasons. But maybe the most unexpected
move, linking back to his other interests, is
getting into the music business. Yeah, reopening
Miraval Studios in France. He partnered with
French producer Damien Quintard in 2021. And
Miraval isn't just any studio, it's legendary.
Pink Floyd, ACDC, The Curia recorded there back
in the day. Exactly. It had been closed for like
two decades. Reopening it in 2022, restoring
it. It feels like more than just a business venture.
It's like preserving a piece of cultural history,
creating a space for artists. It lines up with
his interest in architecture and art later on.
It's about building platforms for creativity,
whatever the medium. Okay, so while Plan B is
making these strategic moves, Pit the Star is
becoming this huge global phenomenon. We mentioned
the Sexiest Man Alive titles. Right, 95 and 2000.
But it went beyond that. He was consistently
on the Forbes Celebrity 100 list in the mid 2000s.
He wasn't just famous. He was powerful. Time
magazine put him on their 100 most influential
people list twice, 2007 and 2009. And the write
up for that was interesting. It wasn't just about
his acting. It specifically mentioned him using
his fame to get people to look to where cameras
don't usually catch. So connecting his stardom
directly to his activism and humanitarian work.
And commercially, he was gold. That Heineken
ad during the Super Bowl in 05. Directed by David.
at Fincher, no less. High -end stuff. Plus deals
with Acura, SoftBank in Japan, Edwin Jeans. His
image sold products globally. Which inevitably
leads us into the territory of his personal life
and the intense media focus. We have to tread
carefully here, stick to what the sources report
impartially. Absolutely. Looking back at his
early relationships in the late 80s, early 90s,
the sources mentioned involvements with co -stars
like Shalane McCall, Robin Givens, Jill Scullin,
Gina Davis, Juliette Lewis. And the sources do
explicitly note the age differences in some cases,
McCall being 15, Lewis 17 when they dated him.
Right. Then, after other high -profile relationships,
like his engagement to Gwyneth Paltrow, came
his marriage to Jennifer Aniston. They met in
98, married in 2000. They were the Hollywood
couple for those five years. The golden couple.
Until the separation announcement in January
2005. That really kicked off a whole new level
of tabloid frenzy. The divorce was final by October.
Though it's worth adding, Pitt said later, I
think in 2009, that they stayed in touch, said
they check in with each other, remained big parts
of each other's lives. Right. But the media narrative
immediately shifted to the relationship with
Angelina Jolie, which began during the filming
of Mr. and Mrs. Smith. Critics even commented
on their thermonuclear screen chemistry. Yeah,
the term Brangelina just exploded. It became
this global shorthand for ultimate celebrity
coupling, and the media obsession was relentless.
They went public when Jolie announced her pregnancy
in January 2006, got engaged in 2012, married
in 2014 at their place in France, Chateau Miraval.
And together they built this large, very visible
family, six children, Maddox, Zahara, and Pax,
who were adopted, and Shiloh, Knox, and Vivienne,
their biological children. The level of scrutiny
on that family was just off the charts. Unprecedented.
And they made a conscious decision to leverage
that attention for charity, especially with the
photos of their children. Right, the first photos
of Shiloh went for millions. 4 .1 to People,
3 .5 to Hello, all donated. And then the twins,
Knox and Vivian. Their first photos broke all
records. $14 million, jointly from People and
Run. Hello, still the most expensive celebrity
pictures ever sold. And again. All the money
went to the Jolie -Pitt Foundation. They turned
the media frenzy into massive philanthropic fuel.
But that intense public interest followed them
through the end of the marriage, too. Jolie filed
for divorce in September 2016. They became legally
single in April 2019. But the custody arrangements
have been ongoing and, frankly, very messy in
public. Pitt initially won joint custody in May
2021, right? He did, which seemed like a resolution.
But then it was overturned just two months later.
The judge was disqualified over concerns he hadn't
fully disclosed business dealings with Pitt's
lawyers. Shows how complicated these things get
under that kind of spotlight. And more recently,
in 2025, reports surfaced about the children's
names. Shiloh legally changed hers to Shiloh
Nouvelle Jolie. Yeah, and reports also say Zahar
and Vivian have stopped using Pitt in their day
-to -day surnames. We also have to address the
controversy surrounding the split. Again, sticking
to the documented facts. The 2016 plane incident.
Right. After that incident, both the FBI and
the L .A. Department of Children and Family Services
investigated Pitt over allegations he was verbally
abusive and physical towards one of the children.
And the key outcome of those investigations?
No criminal charges were filed against him by
either agency. That's a crucial point. However,
the allegations didn't go away. They came up
again in 2022. Yes. During the legal dispute
over the Maryville Winery they co -owned, Jolie
filed a countersuit. In it, her lawyers alleged
Pitt had tried to silence her with an NDA about,
quote, his abuse. And the filing included specific
allegations about that 2016 flight. It did. Allegations
of grabbing, shaking, striking one child, choking
another. These are the claims laid out on the
court documents. We have to be clear these are
allegations within a legal filing. And the public
reaction to all this has been complicated. Very.
There was a Vulture article in July 2025 that
kind of summed it up. It questioned his public
rehabilitation, but concluded pretty bluntly
that maybe the public, or at least the media,
just don't care about the allegations anymore.
Suggesting a sort of fatigue with the whole saga.
Amidst all this turmoil, Pitt himself was going
through significant personal changes. He's been
very open about getting sober. Yeah, he stopped
drinking in September 2016, right around the
time of the split. Started going to Alcoholics
Anonymous. He's even credited Bradley Cooper
publicly for helping him on that journey. And
he linked his past substance use to dealing with
fame. He did. Said back in the late 90s, he was
hiding out, smoking way too much dote, just feeling
lost, turning into a donut was his phrase. He
also mentioned a trip to Morocco, seeing real
poverty kind of jolted him into cutting back
on cannabis then. And then there's the really
unusual health issue he's discussed, prosopagnosia.
Face blindness. He hasn't had a formal diagnosis,
he says, but he talked about it back in 2013
and again more recently in 2022. Struggling for
years to recognize people's faces. Think about
that. for one of the most famous faces in the
world. The irony is huge, isn't it? A job based
on meeting people, collaborating, being public,
and having this condition that makes recognizing
faces incredibly difficult. He admitted it sometimes
makes him just want to stay home. It adds another
layer to understanding his public persona. You
know, a constant thread seems to be this drive
to engage with things beyond acting. His activism
and philanthropy feel deeply connected to who
he is. Definitely. Politically, he supported
John Kerry, Joe Biden. But it's often the specific
causes he campaigns that are revealing, like
pushing for Proposition 71 in California for
stem cell research funding. That was quite specific
and maybe a bit controversial for a big star
back then. It was, but he put himself out there
saying we need to let our best and our brightest
find cures. It showed a willingness to take a
stand on something quite technical and potentially
divisive. And his global focus has been strong,
too. The one campaign against AIDS and poverty
narrating that PBS series on global health. Right.
Rx for survival. Plus significant donations like
that million dollars to Darfur organizations
back in 07. And the Jolie -Pitt Foundation, established
in 2006, wasn't just symbolic. No, they put serious
money in from the start. A million each to global
action for children and Doctors Without Borders
right off the bat. They were active funders.
He was also very vocal about same -sex marriage
equality. He famously said in 2006 he wouldn't
marry Jolie until it was legal for everyone in
the U .S. And he backed it up financially, too,
donating $100 ,000 to fight Proposition 8 in
California in 2008. What's maybe more surprising
to people is his deep interest in architecture.
It wasn't just a casual hobby. Not at all. The
sources say he actually spent time studying computer
aided design CAD at Frank Gehry's office in L
.A. That's serious commitment. Trying to understand
it technically, not just aesthetically. Exactly.
He narrated that PBS series E2 Design about sustainable
architecture. Even co -wrote a book about a specific
historic house, the Blacker House, way back in
2000. This passion directly led to one of his
biggest non -film projects. The Make It Right
Foundation in New Orleans. Yeah, founded in 2006
after Hurricane Katrina. The goal was huge. build
150 sustainable, affordable homes in the devastated
Ninth Ward. And it was a serious architectural
undertaking. Absolutely. It involved 13 different
architectural firms. Pitt put in $5 million of
his own money, which was matched by Steve Bing.
It got recognized by the U .S. Green Building
Council. It was a major effort focused on practical,
sustainable rebuilding. And his creative outlets
keep expanding, especially more recently. It
seems tied into his sobriety journey, too, finding
new forms of expression. Like visual art. He
got really into pottery, started making sculptures.
And this wasn't just a private hobby either.
No. In 2022, nine of his sculptures were actually
exhibited in a major art museum in Finland, the
Sarah Hilden Art Museum. alongside works by Nick
Cave, the musician, and Thomas Halsego, a well
-known artist. From movie star to exhibiting
a sculptor, that's quite an arc. It really is.
Shows that continuous evolution, that search
for mastery in different fields. Okay, let's
bring it back to the acting career, particularly
from the mid -2000s onwards. It feels like his
choices became even more strategic. Big blockbusters
funding the Plan B work mixed with really selective
collaborative roles. Yeah. Even the blockbusters
required immense commitment. Playing Achilles
in Troy back in 2004 that involved six months
of sword training. And the irony there. He actually
injured his Achilles tendon during production.
Delayed the whole shoot. Life imitating art.
Or maybe the other way around. That period also
had some great collaborations. Byrne, after reading
with the Coen brothers in 2008, showed his comedic
side again. People loved him in that. And then
a total shift to working with Terrence Malick
on The Tree of Life in 2011 that... Deep, spiritual,
visually stunning film. And the award nominations
kept coming for his acting. The Curious Case
of Benjamin Button with Fincher again in 2008.
Got him his second Best Actor Oscar nomination.
Remember, his first was way back for Legends
of the Fall. And then Moneyball in 2011, playing
Billy Bean, another Best Actor nom for that one.
Right. He was consistently delivering acclaimed
performances. And at the same time, proving he
could still carry a massive global hit. World
War Z in 2013. Which he also produced through
Plan B. Exactly. Grossed $540 million worldwide.
That was his biggest hit at the time. And think
about it. The same period he's delivering that,
Plan B is winning Best Picture for 12 years,
A Slave. He really perfected running on those
two tracks simultaneously. Which leads us to
the big one, the acting validation he maybe hadn't
quite clinched yet. The Oscar win. Yeah. For
Best Supporting Actor, playing Cliff Booth, the
stuntman, in Quentin Tarantino's Once Upon a
Time in Hollywood in 2019. That felt like the
missing piece of the puzzle, didn't it? His first
Academy Awards specifically for his acting. And
he didn't just win the Oscar. He swept everything
that year. Golden Globes, BAFTA, SAG Award, Critics'
Choice. It was undeniable. It cemented him not
just as a producer who acts, but as a truly accomplished
actor in his own right, capable of these incredibly
nuanced supporting turns that just steal the
show. And he didn't stop delivering those kinds
of performances at Astra in 2019. Playing Roy
McBride, the astronaut. Critics raved about that
one, too. Called it one of his best ever performances.
Talking about how he weaponizes passivity. Really
internal, subtle work. He even picked up an Emmy
nomination for just a cameo. Playing Dr. Fauci
on Saturday Night Live in 2020. Hilarious and
spot on, apparently. Got him a guest actor nomination.
Shows his cultural reach. So looking at the most
recent years, he's still a major force. Absolutely.
Still doing big movies like Bullet Train and
the ambitious, maybe divisive Babylon in 2022.
But the real monster hit recently was F1, the
Formula One movie from 2025. Huge. Reportedly
got a $30 million payday for that role, which
tells you his star power is still right up there.
And the film itself was massive for Apple. Biggest
box office hit they've ever had. Nearly $600
million worldwide, beating World War Z. That
kind of success gives him enormous leverage for
whatever he wants to do next. And he's got wolves
coming up, reteaming with George Clooney. Hashtag
tag, tag, tag outro. So when you pull it all
together, the $9 .3 billion at the box office,
the Oscars for acting and producing, the huge
commitments like make it, right? The personal
stuff he's navigated like sobriety, prosopagnosia.
What defines Brad Pitt now? It feels like it's
that relentless curiosity, that constant pursuit
of creative control. I think that's right. He
consistently seems to value the project, the
team, the vision more than just his own ego or
stardom. He's used his influence, especially
with Plan B, to make challenging, interesting
work happen, all while living under this intense
public microscope. His acting legacy feels pretty
secure now, and F1 proves his commercial power
is still absolutely top tier. So where does he
go from here? He's, what, 61 now? He's got the
acting Oscar. His company just delivered a massive
hit for Apple. He has this incredible creative
and financial freedom. Exactly. And given how
serious he clearly is about architecture, his
growing focus on sculpture, and the kind of high
-level strategic control he has through Plan
B, well, here's the final thought for you, the
listener. What's next? Now that the acting part
is arguably conquered and he has the resources
to do pretty much anything, which creative arena
does he try to master? Does he finally step behind
the camera and direct? Or does he pour that intense
focus into his art, trying to take his sculpture
from being exhibited to being globally recognized?
He seems driven by mastery. And that drive clearly
isn't slowing down. A fascinating place to leave
it for a true Hollywood heavyweight. Thanks for
joining us on The Deep Dive.