Welcome to the Deep Dive. We sift through the
sources, cut through the noise, and really focus
on what matters. Today we're, uh, digging into
a career that seems almost like a contradiction
in terms. Matthew Page Damon. Yeah, Matt Damon.
He's got this like every man vibe, but he's also
this global box office powerhouse. Exactly. And
not just an actor, right? He's consistently worked
behind the camera, screenwriter, producer, even
this ethical entrepreneur kind of figure trying
to shape his own path. It's really the heart
of it, isn't it? That tension. He doesn't just
rent out his fame. He's actually building the
systems he works in. Think about it. He's defined
just as much by, say, the massive success of
the Bourne movies. Huge. As he is by setting
up production companies that are focused on,
you know, fair pay and social issues. Right.
And speaking of success, we should probably put
some numbers on that right away. Yeah. The sources
make it clear his commercial impact is just huge.
Oh, absolutely. Back in 2007, Forbes already
had him ranked as one of the most bankable stars
out there. And that wasn't just popularity, remember?
Yeah. That ranking was about... RY return on
investment. Yeah, what was the number? It was
something like... It was incredible. The analysis
showed he was averaging $29 at the box office
for every single dollar he earned. That's based
on his last three movies at that point. $29 back
for every dollar spent? I mean, if you're a studio
exec, that's almost unbelievable. It proved he
wasn't just critically liked. He was a profit
engine. And by 2010, yeah, the stats put him
up there with the highest grossing actors ever.
But it's not just about the money, is it? He's
got the critical respect, too. Definitely. The
awards back it up. He's got the Oscar for Best
Original Screenplay. For Good Will Hunting, yeah.
Two Golden Globes, one for writing, one for acting
later on. And a Screen Actors Guild Award, too.
Plus tons of nominations. It shows he's seen
as both a performer and a creator. So our mission
today is really to trace that whole arc. From
his college days that led to that breakthrough
script. Right. Through becoming the super reliable
blockbuster lead and then evolving into this
like creative architect role he has now, leading
new companies, dealing with activism. And all
the public attention that comes with that. Yeah.
Let's unpack the whole Damon dossier. OK, let's
start where it all began. Cambridge, Massachusetts.
But maybe not the Cambridge you first think of.
All right. Cambridge, Massachusetts. Born October
8th, 1970. And his early life, looking at the
sources, it really wasn't your standard Hollywood
upbringing. Not at all. His dad, Kent, was a
stockbroker. His mom, Nancy Carlson Page, she's
actually quite well known in her field, early
childhood education professor. But they divorced
when he was really long, right? Like two. Yeah,
it's two. He and his older brother, Kyle, who's
an artist, a sculptor, they moved back to Cambridge
with their mom. And they lived in this six family
communal house. A communal house. That's different.
Definitely not the Hollywood Hills. Right. It
sounds like it fostered independence. But Damon
himself said later that, well, he felt kind of
lonely as a teenager. Really? He mentioned his
mom's approach to child rearing was quite strong.
strict, very academic, and maybe that combined
with the communal living. He said it made it
hard for him to sort of figure out his own identity,
which might be why he gravitated towards acting,
you know. Makes sense. And he got into acting
pretty early. Yeah, he did. He went to Cambridge
Alternative School, then Cambridge Ringe and
Latin School. And that's where the famous partnership
with Ben Affleck really started. Ah, Ringe and
Latin. That connection runs deep. It does. He
gives a lot of credit to his drama teacher there,
Jerry Spica. Called him a major influence. But
didn't he also joke that Spica always gave Affleck
the better parts? He did. With a bit of wry humor,
yeah. Yeah. Sounds like that friendly competition,
that needing to kind of push each other, was
there from the start. Probably fueled both of
them. And that educational path led him to Harvard.
Yep. Harvard University, class of 92. Lived in
Lowell House. He was an English major, did student
theater. And he was in one of those final clubs
too, right? The Delphic Club? He was. Which,
for anyone listening who doesn't know the Harvard
scene, these final clubs are these very old,
very exclusive sort of social clubs. Pretty elite.
But he didn't actually finish Harvard, did he?
No, and this is a key moment. The pull of acting
was too strong. He made this calculated bet that
didn't pay off initially. What happened? He left
Harvard, just 12 credits short of his degree,
12 credits, to take a lead role in a Western
called Geronimo, an American legend. This was
1993. And he thought Geronimo was going to be
his big break. Apparently so. He admitted later
it was a mistake kind of driven by youthful confidence.
He expected it to be this massive hit. And it
wasn't. No, flopped. Yeah. So suddenly he's not
graduating Harvard. The movie didn't launch him.
And he finds himself back in L .A., broke, crashing
in Affleck's apartment, just trying to get any
role he could. Wow. That must have been a tough
period. Crucial, though, because that financial
pressure, that feeling of needing to make something
happen, seems to be what really pushed him and
Affleck to focus on writing something for themselves.
Which brings us to Good Will Hunting. The Breakthrough.
And the origin story is almost mythical now,
but it started pretty small. Wasn't it from a
class assignment at Harvard? Exactly. An essay,
basically. He wrote this short, like 15 -page
play for an English class, and that became the
seed for the character Will Hunting. Just amazing.
So they took that seed. And they worked on it
for years, living together, bouncing ideas, pitching
it around. Apparently they got some pretty wild
notes back from studios early on. Like what?
Oh, suggestions to add more action. Or maybe
someone else should play the leads. You know,
typical development hell stuff. But they stuck
with it. They did. Our sources mentioned they
got really important advice from people like
Rob Reiner and especially the legendary screenwriter
William Goldman. The William Goldman. Wow. What
did he help with? Apparently Goldman really helped
them crack the structure, particularly the ending.
And the whole script just felt real because it
drew so heavily on their own experiences, their
observations of growing up around Cambridge and
South Boston. So when it finally came out in
1997, the impact was huge. Seismic is the word.
Instantaneous. It wasn't just a hit movie. It
was like this cultural moment. Critics loved
it, called it witty, vigorous. Damon's performance
was praised as charismatic. It just immediately
proved they weren't just actors trying to write,
they were writers. And the payoff. Life -altering.
Academy Award Golden Globe for Best Original
Screenplay. The each got paid $600 ,000 for it,
which was... massive for unknowns back then.
600 grand each. Wow. And the film grossed over
$225 million worldwide. Damon said going from
being broke to that level of fame almost overnight
was just... Nearly indescribable. Imagine that,
winning an Oscar in your 20s for something you
started in a college class. It really sets the
tone for his whole career, doesn't it? That idea
that creative control leads to success. Absolutely.
Yeah. But even before the Oscar win, he was showing
this incredible, almost obsessive dedication
to the acting craft itself, especially the physical
side. Right, the transformations, like for Courage
Under Fire. Yeah, that was before Good Will Hunting
even came out in 1996. He played an opiate -addicted
soldier. And to look the part, he dropped, get
this, 40 pounds. That's 18 kilos in just 100
days. How? On his own regimen, self -prescribed
diet and intense exercise, which sounds incredibly
dangerous, frankly. But it got him noticed. Oh,
yeah. Critics called his performance impressive,
but it apparently took a huge toll on him physically.
Then he had to gain most of it back really quickly
for the Rainmaker in 97. And then he lost weight
again soon after. Yep. dropped about 25 pounds,
11 kilos, to play Tom Ripley in The Talented
Mr. Ripley in 99. that manipulative anti -hero
role. So this pattern of intense physical commitment
was there early on. He clearly saw it as part
of building the character. Exactly. And that
kind of dedication really carried over into the
next decade, the blockbuster years. Yeah. Hashtag,
hashtag, hashtag two, franchise star in the blockbuster
decade. So the 2000s arrive and Damon makes this
huge shift. He goes from being the indie darling
who wrote his own ticket to being, well, the
definition of a reliable, bankable, global movie
star. This was really the franchise decade for
him. Yeah, he ended up anchoring two massive
trilogies almost simultaneously. First up was
the Oceans series, starting in 2001. Right, Oceans
11, 12, 13. He played Linus Caldwell, the kind
of rookie thief in that big ensemble. And wasn't
that role originally meant for someone else?
It was. Mark Wahlberg, apparently. He turned
it down, so Damon stepped in. And Oceans 11 was
just... Cool, smooth, and a huge hit. Colossal.
It let Damon flash that sort of everyman charm
within this super stylish ensemble cast, didn't
have to carry the whole thing. And yeah, it made
a fortune, like $450 million worldwide on an
$83 million budget. But the role that really
defined that era for him and cemented him as
an action star was Jason Bourne, starting in
2002. Absolutely, Jason Bourne, the amnesiac
assassin. It's fascinating, though, because he
landed that role when things were actually a
bit uncertain for him. him professionally. Really?
After Oceans? Well, Oceans was big. But remember,
some of his other films around that time, like
All the Pretty Horses in 2000, hadn't done well
commercially. He actually said he was jobless
for about six months before The Bourne Identity
came along. Wow. So Bourne wasn't a guaranteed
hit in his mind. Apparently not initially. He
even had some doubts about whether it would find
an audience. But once he took it, he committed
fully. And how. He didn't just phone it in. The
training was legendary. Totally. He insisted
on doing a lot of his own stunts. He went through
three months of intense training stunt work,
weapons, boxing, and that Filipino martial art.
You see that same discipline again, right? Like
with courage under fire. He wanted it to feel
authentic. Exactly. And critics really responded
to that. Roger Ebert loved the first film, praised
its focus on spycraft, and Damon's ability to
be so focused and sincere made Bourne feel smart
and dangerous, not just a blunt instrument. And
by the time the sequel, The Bourne Supremacy,
came out in 2004, the character was iconic. Totally
iconic. He won an Empire Award for Best Actor
for that one. The critics noted his astute, underplayed
performance, how he avoided typical movie star
vanity. Entertainment Weekly called him one of
the decade's best mixer of brawn and brains.
That really nails the Damon brand at that point,
doesn't it? Smart, grounded action. Perfectly.
But what's interesting is that massive success
didn't totally box him in. In 2006, he's also
in Martin Scorsese's The Departed. Which won
Best Picture? Playing the undercover state trooper
inside the mob. Right. And that role showcased
that other quality we talked about, his ability
to kind of blend into a powerhouse ensemble but
still be totally essential. The New York Times
had a great line about that, didn't they? Something
about his ability to recede into a film while
also being fully present. That's the one. It's
key to his appeal. He wasn't trying to outshine
DiCaprio or Nicholson. He was the relatable guy,
the anchor in the middle of all that chaos, the
audience's way in. So you've got the franchise
lead, the reliable ensemble player. Yeah. It
makes sense that Forbes called him the most bankable
star in 2007. Studios knew he delivered. Huge
return on investment. But that level of success,
being that bankable, also sets up maybe the most
famous what if of his career. The avatar decision.
$250 million mistake, as some call it. It's legendary
now. It just perfectly illustrates the kind of
insane opportunities and tough choices that come
with that level of fame. James Cameron offered
him the lead in Avatar. The lead role, Jake Sully.
Yep. But Damon turned it down. Why on earth?
Loyalty and contracts. He was committed to the
Bourne franchise, filming the Bourne ultimatum,
I believe, and the schedules conflicted. He didn't
want to abandon the series that had been so good
to him. Okay, that's professional integrity.
But the crazy part was the money Cameron offered,
right? That's the kicker. It wasn't just the
role. Cameron offered him 10 % of the film's
profits. 10%. Of Avatar. Yeah. Which became the
highest -grossing film of all time. Exactly.
Do the math on 10 % of what? Nearly $3 billion
worldwide? It's hundreds and hundreds of millions
of dollars. Unbelievable. Damon himself jokes
about it constantly. He's quoted saying, I will
go down in history. You will never meet an actor
who turned down more money. It's kind of amazing
he can laugh about it. Well, it may be easier
to laugh when you're still Matt Damon, but it
shows the scale he was operating on. Absolutely.
And just to keep things grounded, we should mention
not everything he touched. turned to gold in
that decade. There were other non -franchise
films, dramas like All the Pretty Horses or that
fantasy film The Brothers Grimm in 2005. Right,
those didn't really land. No, they were critical
and commercial disappointments. It kind of reinforces
how important those big franchises or prestige
ensemble pieces were for maintaining that bankability
during that specific era. Okay, so after establishing
himself as this massive star, the next major
phase in Damon's career is really about taking
back control. Moving from being the product to
being the architect. Which seems like a direct
line back to the struggles he and Affleck had
getting Good Will Hunting made, right? Absolutely.
You can see that thread. The desire to control
the process, not just the performance. And it
started pretty early. formerly, with their first
production company, Live Planet, back in 2000.
And their big thing was Project Greenlight. I
remember that show. Yeah, the Emmy -nominated
documentary series. It was on HBO, then Bravo.
And it wasn't just reality TV. It was kind of
a mission statement. How so? The whole point
was to find undiscovered filmmakers, give them
funding, document their first real shot at making
a feature film, and actually help launch their
careers. Damon was an executive producer, really
hands -on, trying to guide these first -timers
through the studio system. So nurturing new talent
that might otherwise get ignored? Exactly. It
was about changing the system from within, even
back then. And that focus on changing the system
continued with their next company, Pearl Street
Films, which they started in 2010. Right. Pearl
Street Films, based at Warner Brothers. And they
made a really significant move in 2018 regarding
industry practices. The inclusion writer. That's
it. In March 2018, they announced Pearl Street
would adopt the inclusion writer agreement for
all their future productions. Remind us what
that is exactly. Basically, it's a clause you
can put in a contract that requires a certain
level of diversity in casting and hiring, not
just for actors, but trucially for the crew behind
the camera, too. So using their power as producers
to push for real structural change in who gets
hired in Hollywood. Precisely. A very deliberate,
proactive step. And now their newest venture,
Artists' Equity, founded with Affleck in 2022,
seems like the culmination of all this. It really
does. Artists' Equity feels like the most direct
attack on the old financial model. The core idea
is giving creators the people actually making
the film a bigger, fairer piece of the pie. How
does that work? They use a more data -driven
approach to figure out distribution and value.
But the key thing is offering profit participation,
not just to the big names, the stars, the director.
what they call above -the -line talent, but also
to the below -the -line talent, the crew, the
camera operators, the editors, the costume designers,
the people whose work is essential but who almost
never share in the film's financial success under
the traditional model. That sounds revolutionary,
honestly, giving crew points on the back end.
It's a huge shift. It feels like the goodwill
-hunting ethos talent should be rewarded, applied
across the entire production process. And their
first film... under that banner was air about
nike signing michael jordan yep air came out
in 2023 affleck directed damon starred it did
really well commercially got great reviews and
damon even picked up another golden globe nomination
for it so proof of concept maybe while he's building
these companies he's still acting obviously and
taking on some really interesting roles oh yeah
his acting choices remain strong like in soderbergh's
dark comedy the informant back in 2009 he gained
weight for that one didn't he he did Played Mark
Whitaker, got a Golden Globe nomination. And
critics started talking about how he was quietly
becoming this great everyman actor. Not just
a star, but a character actor, too. And then
Invictus, also in 2009, his first Oscar nomination
for acting. Right. Best Supporting Actor for
playing Francois Pienaar, the South African rugby
captain opposite Morgan Freeman's Nelson Mandela.
And again, the reviews highlighted that grounded
quality, low -key charm and integrity, one said.
Even playing these larger -than -life figures,
he keeps them relatable. That reliability is
his superpower. Which leads us to The Martian
in 2015. Stranded on Mars. That felt like peak
Damon in a way. Smart, resourceful, funny, carrying
a huge movie, mostly by himself. Absolutely.
Directed by Ridley Scott, who was a massive success,
won him the Golden Globe for Best Actor in a
Comedy Musical. Which is a bit odd category wise.
Yeah. A comedy about potentially dying alone
in space. Right. But it got him his second Oscar
nomination for best actor. And it proved he could
anchor a giant blockbuster outside of the Bourne
world. He also went back to writing co -writing
Promised Land in 2012 and The Last Duel in 2021.
Yeah. Back to his roots with Affleck on The Last
Duel. Now that film really highlights the tension
we've been talking about. Well, The Last Duel,
medieval France, complex themes. It got good
reviews, generally. But financially, it bombed.
Really? With Damon, Adam Driver, J .D. Comer,
Ridley Scott directing? Exactly. If that lineup
can't make an original challenging period drama
work at the box office, what does that say about
the market for those kinds of films now? It raises
big questions. It shows his commitment, though,
right? He's still willing to take those creative
risks, even if they don't have the guaranteed
payoff of another franchise entry. Precisely.
The creative control, the quality of the project
seems to trump the guaranteed commercial hits
sometimes. And we have to mention his collaborations
with Christopher Nolan. Oh, definitely. He had
that small but memorable role in Interstellar
back in 2014. Dr. Man, not the nicest guy. No,
definitely not. And then more recently playing
Leslie Groves in Oppenheimer. Right, the military
head of the Manhattan Project. And Oppenheimer,
interestingly, became Dema's highest grossing
film ever. Bigger than born, bigger than oceans.
Wow, that's saying something. And they're working
together again. Supposedly, yes. He's set to
play Odysseus in Nolan's upcoming adaptation
of The Odyssey. That should be fascinating. And
just quickly, he's done some great TV work, too,
showing that versatility. Yeah, Emmy -nominated
guest spots. He was hilarious as Liz Lemon's
pilot boyfriend on 30 Rock. Oh, yeah, Carol Burnett.
And his portrayal of Scott Thorson, Liberace's
lover, in HBO's Behind the Candelabra was incredible.
Earned him an Emmy nomination for that, too.
It just shows he'll go wherever the good writing
is, regardless of the platform. Hashtag tag,
tag, tag, freebie. Activism, advocacy, and public
scrutiny. OK, so beyond the acting and producing,
Damon has put a significant amount of his energy
and fame into activism, particularly around a
couple of key global issues. Yeah, his work on
global water access is really substantial. It
goes back quite a way. He founded the H2O Africa
Foundation and then in 2009 that merged with
another organization, Water Partners, to become
Water .org. And their approach isn't just charity,
right? It's more systemic. Exactly. It's not
just about digging wells, though that's part
of it. The core mission is using microfinance
to help people in developing countries get access
to safe, clean, affordable drinking water and
sanitation. Microfinance for water. How does
that work? They pioneered this model called Water
Credit. Essentially, they help provide small
loans, microloans to families so they can afford
to install taps or toilets in their homes, things
that provide a lasting solution. The idea is
to make it sustainable. And has it been successful?
Seems to be scaling up. Our sources mentioned
Water .org got a big, like, $8 million grant
from the PepsiCo Foundation specifically to expand
that water credit program in India. So the model
seems to be working. And Damon uses his celebrity
to promote this heavily. Oh, yeah. He's front
and center. He's done partnerships with big brands,
Aquafina, Ethos Water, Stella Artois Beer. Remember
that Super Bowl commercial he did for Stella
Artois on Water .org in 2018? Vaguely, yeah,
using that massive platform. Exactly. Leveraging
his fame. directly for philanthropic funding.
He's also involved in other things he co -founded,
not on our watch with George Clooney, Brad Pitt,
Don Cheadle. What does that one focus on? Preventing
mass atrocities, bringing global attention and
resources to crises, like the one in Darfur,
for example. Plus, he's a spokesperson for Feeding
America, the hunger relief organization, and
an ambassador for Onexone, which helps kids globally.
So a serious long -term commitment. to these
causes. Definitely. But like many public figures
who engage in advocacy, his efforts haven't been
without controversy or intense public scrutiny.
It highlights that tension between using your
platform and navigating tricky public perception.
Let's talk about the Crypto .com ad. That got
a lot of attention, mostly negative. It really
did. This was late 2021. Damon announced a partnership
with Crypto .com, this cryptocurrency trading
platform. Part of the deal involved a million
-dollar donation from them to Water .org. Okay,
so a direct benefit to his charity. And didn't
he say his fee went to Water .org too? Yeah,
he was clear that 100 % of his fee for doing
the commercials went straight to the foundation.
But the ad itself, Fortune Favors the Brave,
it didn't land well. Not at all. It came out
in early 2022. The ad basically compared investing
in cryptocurrency to these grand historical acts
of bravery, explorers, astronauts, etc. Which
sounds a bit much. That was the reaction. The
backlash online was huge. People called it insulting,
cringy, disgusting. The criticism was that here's
this incredibly wealthy celebrity encouraging
average people to gamble on this highly volatile,
largely unregulated market. Some even compared
it to promoting a Ponzi scheme. So the charitable
angle got completely overshadowed by the criticism
of the core message. Pretty much. It became a
case study in the potential pitfalls of celebrity
endorsements, especially in new risk financial
areas. That tension between raising money for
a good cause and potentially harming your audience's
financial well -being, it's a tough line. There
was also scrutiny around comments he made during
the height of the Me Too movement. Yes, in late
2017. There were two main incidents. First, related
to Harvey Weinstein. An old story resurfaced
suggesting Damon had tried to kill a negative
article about Weinstein back in 2004. What was
his response? He strongly denied it. He clarified
that he did call the reporter back then, but
only to vouch for the professional reputation
of an executive who ran Miramax's Italy office,
who he felt was being unfairly characterized.
He wasn't calling about Weinstein himself. And
the reporter involved later confirmed Damon's
account of that specific call. OK, so that was
clarified. But there was another comment that
caused more widespread backlash. Right. Around
the same time, December 2017, he gave an interview
where he talked about sexual misconduct needing
to be viewed on a spectrum of behavior. Meaning
what exactly? His point seemed to be that there's
a difference between, say, telling an inappropriate
joke or patting someone on the back and acts
like rape or child molestation, and that the
response should perhaps be. different depending
on the severity. And that didn't go over well.
Not at all. It sparked immediate criticism. People
felt it was incredibly tone deaf, that it minimized
the harm caused by all forms of misconduct, and
that creating a spectrum could be used to excuse
or downplay abuse. It was seen as missing the
larger point about power dynamics and systemic
issues. How did he react to the backlash? He
addressed it publicly a month or so later in
January 2018. He essentially apologized, acknowledged
he hadn't understood the perspective of people
who felt marginalized, and said he realized he
should probably get in the backseat and close
my mouth for a while. So a public learning moment,
it sounds like. It seemed that way. A recognition
that his perspective as a powerful man in the
industry perhaps wasn't the most helpful one
at that moment. And there was one more recent
controversy about language. Yes, in 2021. He
mentioned in an interview that he had recently
stopped using the homophobic slur fag after his
daughter called him out on it. He claimed it
was a word commonly used when he was younger,
supposedly with a different application, not
necessarily as a slur against gay people. He
said his daughter wrote him this very long, beautiful
treatise explaining why the word is dangerous
and hurtful, regardless of intent. He was careful
to say he'd never use the more extreme version,
faggot. So, again, learning from a different
perspective, in this case, his daughter's. Exactly.
It highlighted a generational shift in understanding
the impact of language. He publicly credited
her for educating him. Shifting to more standard
politics, the sources say he's a Democrat supporter.
Generally, yes. Longtime supporter of the Democratic
Party. He hosted a fundraiser for Elizabeth Warren
back in 2012. He's also been very outspoken about
wanting stricter gun control laws, saying things
like, I actually hate guns. They freak me out.
And it hasn't always towed the party line. No.
He actually expressed some public disappointment
with President Obama's policies while Obama was
in office, felt maybe there wasn't enough substantive
change happening. So he's willing to criticize
even within his own party affiliation. Hashtag
tag tag tag V personal life and cultural footprint.
All right. Let's shift gears a bit from the heavy
stuff, the production deals, the controversies
and look at the personal side and maybe the lighter
aspects of his public image. Sure. Behind all
the career moves, there seems to be a pretty
stable personal foundation. He married Luciana
Bazzambroso back in 2005. How did they meet?
Wasn't it kind of random? Yeah, pretty famously
random. He met her in Miami in 2003 while he
was filming the Farrelly Brothers movie Stuck
on You. She was working as a bartender, apparently.
That's a great story. And they have kids. They
have three daughters together. And Luciana had
a daughter from a previous relationship who Damon
considers his own. People often point to that
stable family life as maybe enabling him to take
some of those bigger professional risks. Where
do they live? He seems like a bi -coastal guy.
He's definitely lived in different places. Miami
for a while, New York City, Los Angeles, Pacific
Palisades area. But then in 2018, he bought this
massive, record -breaking penthouse apartment
in Brooklyn Heights, New York. Brooklyn Heights.
For how much? I think it was around $16 .5 million.
Set a record for Brooklyn real estate at the
time. So strong ties to New York as well as L
.A. And being a Boston guy, you have to mention
the Sports Connection. Oh, absolutely. Diehard
Boston Red Sox fan. Threw thick and thin. He
even narrated the official World Series DVD when
they won back in 2007. Nice. And didn't he play
poker, too? Like, seriously. Echoes of Rounders?
He did. His character, Mike McDermott, in Rounders
wasn't totally fictional in that sense. He actually
competed in the World Series of Poker a few times
back in the day. Did he do okay? Well, he famously
got knocked out of the 1998 WSOP main event by
the legendary Doyle. brunson so maybe stick to
acting for the big money oh okay but maybe the
most fun enduring part of his public persona
is the whole thing with jimmy kimmel oh the feud
it's brilliant just this long running gag that's
been going on for what almost 20 years now it
started super simple right Kimmel just saying
he ran out of time for Matt Damon at the end
of the show. Exactly. Back in 2006 on Jimmy Kimmel
Live. Just a throwaway joke that Kimmel apparently
did on a whim because the show was running long
one night. And it just escalated beautifully
from there. Into this elaborate, ongoing performance
art piece. Remember Sarah Silverman's video?
I'm fucking Matt Damon. She was dating Kimmel
at the time. Oh, my God. Yes, that was hilarious.
And Damon was in it. He was. And then Kimmel's
perfect response video. I'm fucking Ben Affleck
with Affleck and like half of Hollywood making
cameos. It brought it right back to the original
Affleck partnership. Genius. And then there was
the time Damon actually took over. Kimmel's show
in 2013, tied him up and finally demanded his
interview slot. The commitment to the bit is
incredible from both of them. It really is. Yeah.
And the fact that Damon, this huge movie star,
is so willing to participate in that kind of
self -mockery, it just reinforces that accessible
everyman quality people love about him. It makes
him seem grounded, even when he's playing, you
know, a super spy or an astronaut. Definitely
adds to his likability. And he's received official
honors, too, beyond the film awards. Yeah, he
got his star on the Hollywood Walk of Fame in
2007. And maybe more significantly, given his
origins, he received the Harvard Arts Medal in
2013. Bringing it full circle back to Cambridge
and Harvard. Exactly. Acknowledging that journey
from dropout to, well, global figure and influential
producer. Hashtag, tag, tag, outro. So when we
try to pull all these threads together. What's
the big picture on Matt Damon? What does the
dossier tell us? Well, I think you see this fascinating
fiasco who operates on two levels simultaneously.
On one hand, he's got that incredible commercial
reliability, the guy who delivers that $29 return
for every dollar the studio spends, the born
guy, the oceans guy. The bankable star. Right.
But at the same time, he seems fundamentally
driven to resist. Just being that commodity,
he's constantly pushing for more creative control,
taking risks, investing personally in changing
the system. It's a real balancing act. You've
got the large scale, serious philanthropy with
Water .org focusing on these innovative microfinance
solutions. Sustainable change. And then you have
these moments where his public statements, whether
it's about crypto or social issues, draw intense
criticism and require, you know, some public
recalibration. Yeah, the high profile advocacy
comes with high profile. scrutiny. It's part
of the territory when you operate at that level.
But underlying it all seems to be this consistent
theme, the fight for control. It started with
him and Affleck writing Good Will Hunting because
the system wasn't giving them the roles they
wanted. Right. Bypassing the gatekeeper. And
now, decades later, his newest company, Artists'
Equity, is explicitly designed to give more power
and financial reward back to the creators, even
the below the line crew. It really brings it
full circle, which leads to, I think, the final
provocation for you, the listener, to think about.
What's that? When we look back on Matt Damon's
entire career, decades from now, what will ultimately
define his legacy? Which side of the camera wins
out? Is it the actor? The massive, reliable,
Oscar -nominated star of films like The Martian,
Oppenheimer, The Bourne series? That guy? Or
is it the producer and writer? The guy who started
with Good Will Hunting? who launched Project
Greenlight, who's now trying to fundamentally
reshape how Hollywood compensates talent with
artists' equity. The actor versus the architect.
Exactly. Where does the balance tip? It's a career
built on this idea that real success isn't just
starring in the story. It's maybe about owning
the script itself. A lot to think about there.
We have been deep inside the demon dossier. Thanks
for joining us on The Deep Dive.