Welcome to the Deep Dive. Today, we're tackling
a figure who's, well, practically defined by
contradiction, Sean Penn. Yeah, it's quite the
subject. You've got this incredibly intense,
decorated actor on one hand. Two Oscars, right?
Two Oscars, yeah. And then on the other, this
deeply involved, sometimes really controversial
global activist. Someone who seems just as comfortable
on a film set as, I don't know, in a war zone
or mediating some kind of international dispute.
It's a lot. It is. And our sources cover pretty
much everything. His whole career, really, from
the mid -70s up to, well, basically yesterday,
with his activism. So the mission today? The
mission is to sift through it all, find the connections,
you know. How does the actor relate to the activist?
How does that same intensity fuel both the acclaimed
performances and, frankly, some of the personal
turmoil and political controversies? We want
to see how he built his career, how the lines
blurred between his public persona, his private
life, his legal issues. And his... very direct
involvement in some major global events, all
while, you know, just preventing the facts from
the sources. We're not taking sides here. Exactly.
So for you listening, this is the shortcut to
understanding this really unique, often baffling
public figure. We'll trace it from his early
days through the Hollywood highs and lows, the
legal battles, right up to his current focus.
OK, let's dive in. Where does this intensity
start? The early years. So, Sean Justin Penn,
born 1960, Santa Monica, and his family background,
it's pure Hollywood, isn't it? Oh, completely.
You've got Leo Penn, his dad, an actor and director,
and his mom, Eileen Ryan, also a respected actress.
Right, and Nucci was her maiden name. Yeah, so
he grew up surrounded by it. The craft, the industry.
It was literally in the house. And the heritage
is interesting, too. Mixed background. Mm -hmm.
Father's side, Jewish. His grandparents emigrated
from Lithuania, actually, Myrkina. Okay. And
his mother's side, Catholic, Irish, and Italian
roots. He wasn't raised religious. No, the sources
say it was a secular upbringing out in Malibu.
Malibu back then. Must have been quite the place.
And he was already making films as a kid. Yeah,
with his buddies, who just happened to be, you
know, Emilio Estevez, Charlie Sheen. Wow. So
that whole group knew each other from way back,
making short films together in junior high and
high school. Exactly. Malibu Park Junior High,
Santa Monica High. Imagine that little film crew.
Probably pretty competitive, even then. That
intensity likely started early. And his actual
first screen appearance was unexpected. Yeah,
very low -key. 1974, an uncredited extra. On
Little House on the Prairie, of all things. No
way. Yeah, his dad directed the episode, so a
foot in the door, but literally in the background.
But he moved on pretty quickly from that. Oh,
yeah. By 1981, he's got his feature film debut
in Taps, playing a military cadet. Serious stuff.
And Broadway, too. Yeah. Same year, 1981, in
a play called Heartland. But then came the role
that, well, everyone remembers from that era.
Ah, Jeff Spicoli. Fast Times at Ridgemont High,
1982. The ultimate surfer stoner dude. Totally
iconic. And the sources actually credit his character
with helping push the word dude into mainstream
conversation. Which is kind of amazing. But you
get the sense he immediately wanted to distance
himself from Spicoli. Oh, absolutely. His very
next big role was a complete U -turn. Bad Boys,
1983. Playing Mick O 'Brien, this really troubled
kid. Exactly. And that's where the critics really
started noticing him as a serious, dramatic actor.
Got great reviews. It sort of set the template,
you know? Yeah. Intensity, focus, diving deep
into troubled characters. He wasn't going to
be just Spicoli. And that intensity, it wasn't
just on screen, was it? It started showing up
in his life choices, connecting his roles to
real world actions. Definitely. A prime example
is The Falcon and the Snowman in 85. Where he
played Andrew Dalton Lee. the real guy convicted
of spying for the Soviets. Right. Lee got life,
but was paroled much later in 98. Penn obviously
had to research him, get into his head for the
role. And then he did something pretty unconventional
after Lee got out. Yeah, this is fascinating.
He hired Lou as his personal assistant. Wow.
Why? Well, the sources suggest two main reasons.
One, sort of a thank you to Lee for letting him
portray him. And two, a genuine belief in rehabilitation.
Lee had done his time and Penn seemed to feel
strongly about helping him reintegrate. It's
this early sign of him using his influence platform
for something directly linked to a role, but
with real world consequences. Taking a stand,
basically. Exactly. And that same conviction,
maybe that same intensity, led him to step back
from acting for a bit in the late 80s, early
90s. Why the break? Seems he was just dissatisfied
with the industry, the roles, maybe the sources
mentioned that. So he decided to focus on directing
instead. Which led to his directing debut. The
Indian Runner, 1991. Based on a Bruce Springsteen
song, Highway Patrolman. So he wasn't just duping
his toe in. He was serious about directing. Very.
It established him as someone interested in telling
raw, character -focused stories from behind the
camera, too. not just the leading man. So when
he comes back to acting in the 90s, he comes
back with a vengeance, right? This is where he
really cements himself as a major force. Hashtag
tag tag tag 2 .1, establishing stardom and critical
dominance, 1990s. Oh, absolutely. The 90s are
arguably his peak in terms of just pure acting
dominance and transformation. Like in Carlito's
Way. Yeah, 1993, playing that sleazy, ambitious
lawyer, David Kleinfeld. Total transformation,
the hair, the voice. Everything. Got a Golden
Globe nomination for that one. Critics were raving
about how he just embodied this corrupt character.
But the big one, the one that really vaulted
him into the top tier, was Dead Man Walking.
1995. Playing Matthew Ponslet, the death row
inmate. Racist. Murderer. Just a terrifyingly
intense, quiet performance. His first Oscar nomination.
Yes, and that's when Roger Ebert called him the
most powerful actor of his generation. High praise.
He really committed to these dark, difficult
roles. Totally. He wasn't afraid of them, and
he kept winning awards. Best actor at Cannes
in 97 for She's So Lovely. Right, the romantic
drama. Showing some range there. Exactly. And
then another Oscar nomination just two years
later for Sweet and Lowdown. Woody Allen's film.
Playing the fictional jazz guitarist, Emmett
Ray. Yeah, egotistical, kind of flawed character,
another complex role, another nomination. He
was just incredibly consistent. Moving between
these really different characters, different
styles. And all this time, he's still directing,
too. He did The Crossing Guard in 95. And what
was the critical take on his directing style?
Generally focused on that same intensity, you
know. Critics talked about a raw searching style,
a focus on brute emotional force, very much aligned
with his acting. Hashtag tag tag 2 .2 the Oscar
years and genre flexibility 2000. Okay, so the
2000s is where the Academy Awards really start
coming in. Kicked off with his third nomination
for I Am Sam in 2001. Playing the father with
a developmental disability. Right. But the first
win came a couple of years later, 2003, Mystic
River. Ah, yes. Playing Jimmy Markham, the father
seeking revenge after his daughter's murder.
Incredible performance. Just raw grief and rage.
And that one swept the board. Oscar, Golden Globe,
Critics' Choice. He was definitely on a roll.
And showing flexibility too, right? Wasn't 21
grams around the same time? Same year, 2003.
Totally different film, nonlinear, psychological
drama. Got a BAFTA nomination for that. He was
really operating at his peak. And then came the
second Oscar win for a role that felt different,
more outwardly heroic in a way. Harvey Milk in
Milk 2008. Playing the gay rights activist and
politician. Yeah, a massive transformation again.
But capturing Milk's... optimism his energy his
uh his charisma the reviews were phenomenal people
talked about him completely disappearing into
the role they did words like transmigration were
used like he inhabited milk it won him the second
best actor oscar plus the screen actors guild
award so he's playing this iconic historically
significant figure And around the same time,
his directing work is also getting major recognition.
Absolutely. Into the Wild, 2007, the biographical
survival story. About Christopher McCandless.
Right. And that film was a huge critical success
for him as a director. It got him a Directors
Guild of America nomination, which is a big deal.
So directing wasn't just a side project. It was
a serious parallel career track. Definitely.
He proved he could excel on both sides of the
camera at the highest level. So as his career
moves into, say, the last decade or so, we see
him shifting gears again, moving into television.
Yeah, which is interesting. A lot of big film
actors started doing high -profile TV around
then. He jumped in, too. Like with The First.
Right, 2018. That Hulu series about the first
manned mission to Mars, he played the lead astronaut,
Tom Haggerty. And it's funny, even then, critics
were still bringing up... Spicoli, yeah. One
review mentioned he was still... game to be a
goofball that Spicoli was still in there somewhere.
That shadow really follows him, doesn't it? Even
in a serious sci -fi drama. Seems like it. Then
he did another big TV role, requiring even more
transformation, Gaslit, in 2022. Playing John
Mitchell, Nixon's attorney general during Watergate.
Yeah, under heavy prosthetics. A completely different
kind of role again. Historical, political thriller.
Shows his range is still there. But maybe the
biggest recent shift isn't acting or directing.
It's... Writing. It seems so. He published a
novel in 2018, Bob Honey, who just do stuff.
Satirical thing. And a follow up. Yep. Bob Honey
sings Jimmy Crack Corn in 2019. And he made some
pretty strong statements about this shift, didn't
he? He did. Very public. Said writing would,
quote, dominate my creative energies for the
foreseeable future. Wow. And he said something
about filmmaking, too. Yeah, that he no longer
had a generic interest in making films, which
is a pretty definitive statement from a two time
Oscar winner and respected director. So it sounds
like he's consciously redirecting that famous
intensity away from film towards literature.
And as we have to discuss his activism. Exactly.
Which brings us to the other side of the coin,
the personal turmoil and the headline grabbing
activism. Right. Because you really can't talk
about Sean Penn without talking about the volatility,
the controversies that often ran parallel to
his acting success. No, they're deeply intertwined,
starting with his high -profile relationships.
Hashtag, tag, tag, tag, 3 .1 marriages and high
-profile relationships. Before Madonna, there
were others, right? Elizabeth McGovern, Susan
Sarandon. Yeah, early relationships. But the
marriage to Madonna in 85, that really put his
private life and his temper under a global microscope.
They got married right around her birthday, his
birthday. Big media event. Huge. She dedicated
True Blue to him, called him the coolest guy
in the universe. It was this massive celebrity
power couple moment. But it soured pretty quickly.
Or at least the public perception did. Well,
the sources are clear the marriage was marked
by conflict. Specifically, it mentions Penn's
violent outbursts against the press. He was constantly
clashing with paparazzi. And that led to legal
issues, which we'll get to. But the marriage
itself was unstable. Seems so. She filed for
divorce in 87, then withdrew it, then filed again
in early 89, and that time it stuck. And for
years there were these persistent rumors and
allegations about domestic violence. Right. That
narrative was out there for a long time in tabloids
and even some biographies. But Madonna addressed
it directly later on. Crucially, yes. In 2015,
she issued a formal statement, denied he'd ever
struck her, called the stories completely outrageous,
malicious, reckless, and false. So that official
denial is a key part of the record. It complicates
the earlier narrative significantly. Absolutely.
Highlights how public perception and reality
can diverge, especially with intense media scrutiny.
After Madonna, He had a long relationship with
Robin Wright. Very long. They were together for
years before marrying in 96. Had two kids, Dylan
and Hopper. But that marriage also had its share
of ups and downs. Definitely. They actually split
briefly in 95 before they got married. He dated
Jewel during that time. Oh, Ray. And then after
marrying between 2007 and 2009, it was this cycle
of filing for divorce or separation, then reconciling,
then filing again. Very turbulent publicly. Until
it finally ended in 2010. Yeah, the divorce was
finalized then. And more recently. There was
Charlize Theron. From about 2013 to 2015. Lots
of media buzz, engagement rumors. But she denied
they were ever engaged. Right. She clarified
that later. Then a brief marriage to Layla George,
daughter of Vincent D 'Onofrio. Married in 2020.
She filed for divorce about a year later. Finalized
in 2022. So a pattern of intense but often short
-lived or tumultuous relationships. Seems to
be. And his current relationship, starting in
2023, is with Olga Korchayeva, who is Ukrainian.
Which connects directly to his recent activism
focus. Interesting. Yeah, the personal and the
political often seem to intersect for him. Hashtag,
tag, tag, tag, 3 .2, a history of legal issues.
Okay, let's talk about the legal side. Yeah.
Because his temper, especially with the press,
led to actual charges and even jail time. It
did. There's a clear pattern, especially in the
80s. Starts around 85 in Nashville. What happened
there? He pled no contest to assaulting two journalists
trying to photograph him and Madonna. Got fined.
Just a fine. Yeah, 50 bucks each charge. But
then early 86. charged with assaulting a correspondent
in Macau. Then June 86, misdemeanor battery charge
for allegedly hitting songwriter David Wolinsky
in a nightclub. Over Madonna again. Wolinsky
claimed Penn accused him of trying to kiss her.
So, yeah, repeated confrontations. And these
incidents eventually caught up with him. Led
to jail. Right, because he was on probation from
those earlier incidents. In April 87, while filming
Colors, he punched an extra on set. Just punched
an extra. Or apparently. That violated his probation,
resulted in a 60 -day jail sentence for the assault
and reckless driving. Did he serve the full time?
No, he served 33 days. But still, actual jail
time. A pretty serious consequence. And there's
that wild story from when he was inside. Oh,
the Richard Ramirez anecdote? Yeah, Penn wrote
about this himself. He was in the same jail as
the Night Stalker. Apparently. Ramirez recognized
him, wrote him a note. And Penn's response? Classic
Penn, really. Wrote back immediately saying he
felt zero connection and hoped Ramirez got the
gas chamber. Just blunt, harsh moral judgment.
Wow. Even in jail, corresponding with a serial
killer. Okay, fast forward a couple of decades.
The temper issues didn't entirely disappear.
No. 2009, another run -in with a photographer,
Frank Madeljian. Highly publicized. What was
the outcome of that one? pled no contest again
to a misdemeanor in 2010, but the sentence was
steeper this time. How so? 300 hours of community
service and 36 hours of mandatory anger management
counseling. The court was clearly trying to address
the pattern. And then there's the Lee Daniels
lawsuit in 2015. This seems different, more about
reputation management. Exactly. Daniels made
comments in an interview linking Penn to a rumored
history of domestic violence while defending
another actor, Terrence Howard. And Penn sued
for defamation for $10 million. Yep. But the
basis of the suit was very specific. Penn argued
he had never been arrested for or charged with
domestic violence. Ah, so focusing on the legal
record, not necessarily denying any and all past
behavior. Precisely. It was a strategic legal
move. And it worked, in a way. How so? The suit
was dropped in 2016, but only after Daniels publicly
apologized and retracted the statement. Penn
made his point, very forcefully, about how his
past could be legally characterized. It's like
that same intensity that refusal to back down
was channeled from physical confrontation into
legal strategy. Yeah, it's a fascinating evolution.
And that same energy then gets poured into his
political activism, which becomes increasingly
high stakes. Right, because his activism isn't
just signing petitions. He puts himself right
in the middle of things, often controversially.
Oh, absolutely. He goes from fighting paparazzi
to, well, engaging with... presidents and warlords.
It's a major shift. This really ramps up during
the lead up to the Iraq war, right? With that
ad in the Washington Post. Yeah. October 2002
cost him a reported $56 ,000. $56 ,000 for an
ad. Yep. An open letter directly to President
George W. Bush urging him not to invade Iraq.
What else did it say? It was pretty sharply critical,
accused the administration of dismantling civil
liberties, having this simplistic and inflammatory
view of good and evil. Strong stuff. And he didn't
just write letters. He went there. He did. Visited
Iraq briefly in December 2002. Then in 2005,
he went to Iran. As an actor? No, as a journalist.
Okay. For the San Francisco Chronicle, attended
a Friday prayer service at Tehran University.
He was embedding himself. Of course, this kind
of high -profile celebrity activism invites parody.
Right. Team Angarica, World Police, the 2004
film from the South Park guys. They really went
after him. Oh, yeah. Portrayed him as this naive
idealist talking about Iraq having rainbow skies
and rivers made of chocolate. Pure satire. And
Penn's reaction was predictable. Let's just say
he wasn't amused. wrote this furious letter back
to Trey Parker and Matt Stone, sarcastically
invited them to tour Iraq with him, basically
told them off. He doesn't take criticism lightly.
Not at all. And his own political language was
often just as harsh. He called Dick Cheney and
Condoleezza Rice villainously and criminally
obscene people. So not exactly diplomatic. No.
He was using his platform to voice really strong,
often inflammatory opposition. But at the same
time, he was also getting involved in hands -on
humanitarian work. Yeah. Like after Hurricane
Katrina. Yeah, September 2005, he went down to
New Orleans. The sources say he was physically
involved in rescues, pulling people from flooded
homes. But that effort drew criticism too, didn't
it? The whole PR stunt accusation. It did. Because
he had a photographer with him. Critics questioned
his motives. How did he respond? He wrote an
article for HuffPost defending himself. Denied
it was a stunt, said it was genuine aid. But
it shows that dilemma, right? Can a celebrity
do good work without it being seen through the
lens of fame? A constant challenge for famous
activists. But his efforts became much more organized
after the Haiti earthquake in 2010. Massively
so. That's when he founded JP Haitian Relief
Organization, JPHRO. And this wasn't just writing
a check. No, this was a huge operational commitment.
They ran a camp for like 55 ,000 displaced people.
He was very hands -on, very visible there for
a long time. To the point where he got an official
title. Yeah, this is remarkable. In 2012, Haiti's
President Michel Martelly appointed him ambassador
at large for Haiti. Ambassador at large. The
first non -Haitian citizen ever to hold that
diplomatic role. Shows the depth of his commitment
there. And that work evolved into CORE. Right.
Community organized relief effort. CORE expanded
beyond Haiti, became very active during the COVID
pandemic in the U .S., setting up free testing
sites. So significant logistical and humanitarian
work. Right. But even CORE faced some controversy.
It did, specifically around labor issues. What
happened? In late 2021, the National Labor Relations
Board, the NLRB, filed a complaint. Against Penn
and CORE. Yes. Alleging that Penn had... impliedly
threatened employees. Threatened them for what?
For complaining about working conditions. The
complaint mentioned demands for 18 -hour workdays
during the intense COVID response period. So
that same intensity he applies to everything
else maybe created issues within his own organization.
That's what the complaint suggests. That the
demanding all -consuming approach might have
clashed with standard labor practices and worker
protections. Hashtag tag tag 4 .3 controversial
global alignments. Okay, this is where things
get really complex. His alignments with certain
world leaders, especially considering his progressive
image from rolls like milk. Yeah, this is probably
the most pointed area of contradiction for many
observals. His friendship with Hugo Chavez, the
late president of Venezuela. Chavez was known
for his anti -U .S. stance, but also for increasingly
authoritarian moves. Right. But Chavez publicly
praised Penn, read his anti -Bush letter on TV,
and Penn became a staunch defender of Chavez.
To the point of defending his regime against
criticism. Very much so. Famously, in 2010, Penn
called for journalists who called Chavez a dictator
to be jailed. Jailed. For calling a leader a
dictator. That's what he said. And when Chavez
died, Penn called him a global champion for the
poor. Unwavering support. And he also met with
Raul Castro in Cuba. Interviewed him in 2008.
So the core criticism here is. The clash with
his image as a champion of rights, especially
LGBTQ plus rights given milk. Both the Chavez
and Castro regimes had poor records on LGBTQ
plus issues. How did the sources explain this?
Does he address the contradiction? Not directly
in the materials we reviewed. It seems for Penn,
maybe the anti -imperialist stance or the focus
on poverty alleviation in those specific relationships
took precedence over alignment on social issues.
He seems to compartmentalize his alliances. Willing
to overlook certain aspects for a perceived greater
good, perhaps? Perhaps. Or maybe he just saw
those leaders differently than their critics
did. It's hard to say definitively from the outside.
But the contradiction is stark. And then came
maybe the most controversial meeting of all,
El Chapo. Yeah, 2016. While Joaquin El Chapo
Guzman, the head of the Sinaloa cartel, was a
fugitive, Penn secretly met him. How did that
even happen? It was brokered by the Mexican actress,
Kite Del Castillo. The goal was an interview
for Rolling Stone. And the details were just...
Bizarre. Totally. Leaked texts later suggested
El Chapo barely knew who PIN was. He was more
interested in Caita Castillo. What was the official
reaction? Not good. The White House called the
interview maddening, said it potentially interfered
with efforts to capture Guzman. Did PIN face
legal trouble over it? Mexican authorities investigated,
wanted to question him. It was a major international
incident, blurring the lines between journalism,
activism and, well, associating with one of the
world's most wanted criminals. It really demonstrates
his willingness to operate way outside conventional
boundaries. No fear of the risk, it seems. None
whatsoever, which we also saw maybe less dramatically,
but still controversially with the Falklands
issue. Right. 2012. meeting with Argentina's
president, Cristina Fernandez de Kirchner. And
he wades right into the sovereignty dispute with
the UK over the Falkland Islands, or Malvinas,
as Argentina calls them. What exactly did he
say? He talked about opposing ridiculous demonstrations
of colonialism and pushed for dialogue. Which
predictably caused outrage in Britain. Oh, yeah.
British tabloids and politicians slammed him,
called his comments moronic. Did he walk it back?
He clarified later, said his comments were misrepresented,
that he was really criticizing Prince William's
military deployment there as preemptive intimidation.
He framed it as opposing militarism, advocating
for diplomacy and negotiation, even suggesting
things like immigration changes. Hashtag hashtag
4 .4 advocacy and conflict in Ukraine. So that
brings us to his most recent and perhaps most
sustained geopolitical focus. Ukraine. Right.
This seems to be where a lot of his energy has
been directed lately. He was there in 2022 filming
a documentary. Superpower. profiling president
zielinski exactly he was embedded meeting officials
attending briefings right up close and he was
actually there when the full -scale invasion
began he was which led to that incredible story
of him and his team having to abandon their car
and walk for miles to the polish border to get
out that's intense real personal risk absolutely
and his statements afterwards were completely
unambiguous total support for ukraine like that
quote about america losing its soul If we allow
Ukraine to fight alone, our soul as America is
lost. Very strong words. Led to Russia sanctioning
him, putting him on their blacklist. And then
came that symbolic gesture in Kyiv. The Oscar
loan. November 2022. Yeah. He physically gave
one of his Oscar statuettes to President Zelensky.
What was the condition? When you win, bring it
back to Malibu. Just the simple, powerful symbol
of faith and solidarity. And Zelensky gave him
something in return. The Ukrainian Order of Merit,
a formal state honor. It really cemented his
role as a high profile international advocate
for Ukraine's cause. It's quite an image. The
Hollywood Award traded temporarily for a wartime
medal. It encapsulates so much about him. Hashtag
tag outro. It really does. When you look back
at everything we've covered, that duality is
just. It's inescapable. You have this incredible
actor capable of these deep, transformative,
award -winning performances. Mystic River, Milk,
Dead Man Walking. Intense commitment to the craft.
But then you have the other Sean Penn, the activist.
Volatile, yes, but also deeply engaged, willing
to dive headfirst into incredibly complex, dangerous
situations. Katrina rescues, building camps in
Haiti, the Chavez friendship, the El Chapo meeting,
walking out of Ukraine. It's the same intensity
applied in radically different arenas. Those
leading to acclaim, sometimes to controversy,
sometimes to legal trouble. Exactly. So for you
listening, the key takeaway is that this commitment,
this intensity is the engine driving both the
artistic triumphs and the real world controversies.
You can't really separate them. He's resisted
simple labels his entire career. And we saw how
he won his highest acting honors portraying a
celebrated gay rights hero in Milk. But then
he strongly defended. leaders like Chavez and
Castro, whose governments had documented anti
-LGBT policies. That's the central paradox, isn't
it? It really is. And it leaves us with a question
to think about. In today's world, with constant
scrutiny, can this kind of intense, sometimes
contradictory celebrity activism function effectively
in the gray areas of global politics? Or is it
always going to be defined and maybe judged by
its most glaring inconsistencies? Something to
ponder.