WEBVTT

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Welcome to the Deep Dive. Today, we're tackling

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a figure who's, well, practically defined by

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contradiction, Sean Penn. Yeah, it's quite the

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subject. You've got this incredibly intense,

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decorated actor on one hand. Two Oscars, right?

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Two Oscars, yeah. And then on the other, this

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deeply involved, sometimes really controversial

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global activist. Someone who seems just as comfortable

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on a film set as, I don't know, in a war zone

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or mediating some kind of international dispute.

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It's a lot. It is. And our sources cover pretty

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much everything. His whole career, really, from

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the mid -70s up to, well, basically yesterday,

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with his activism. So the mission today? The

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mission is to sift through it all, find the connections,

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you know. How does the actor relate to the activist?

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How does that same intensity fuel both the acclaimed

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performances and, frankly, some of the personal

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turmoil and political controversies? We want

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to see how he built his career, how the lines

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blurred between his public persona, his private

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life, his legal issues. And his... very direct

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involvement in some major global events, all

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while, you know, just preventing the facts from

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the sources. We're not taking sides here. Exactly.

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So for you listening, this is the shortcut to

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understanding this really unique, often baffling

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public figure. We'll trace it from his early

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days through the Hollywood highs and lows, the

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legal battles, right up to his current focus.

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OK, let's dive in. Where does this intensity

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start? The early years. So, Sean Justin Penn,

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born 1960, Santa Monica, and his family background,

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it's pure Hollywood, isn't it? Oh, completely.

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You've got Leo Penn, his dad, an actor and director,

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and his mom, Eileen Ryan, also a respected actress.

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Right, and Nucci was her maiden name. Yeah, so

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he grew up surrounded by it. The craft, the industry.

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It was literally in the house. And the heritage

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is interesting, too. Mixed background. Mm -hmm.

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Father's side, Jewish. His grandparents emigrated

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from Lithuania, actually, Myrkina. Okay. And

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his mother's side, Catholic, Irish, and Italian

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roots. He wasn't raised religious. No, the sources

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say it was a secular upbringing out in Malibu.

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Malibu back then. Must have been quite the place.

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And he was already making films as a kid. Yeah,

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with his buddies, who just happened to be, you

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know, Emilio Estevez, Charlie Sheen. Wow. So

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that whole group knew each other from way back,

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making short films together in junior high and

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high school. Exactly. Malibu Park Junior High,

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Santa Monica High. Imagine that little film crew.

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Probably pretty competitive, even then. That

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intensity likely started early. And his actual

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first screen appearance was unexpected. Yeah,

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very low -key. 1974, an uncredited extra. On

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Little House on the Prairie, of all things. No

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way. Yeah, his dad directed the episode, so a

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foot in the door, but literally in the background.

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But he moved on pretty quickly from that. Oh,

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yeah. By 1981, he's got his feature film debut

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in Taps, playing a military cadet. Serious stuff.

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And Broadway, too. Yeah. Same year, 1981, in

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a play called Heartland. But then came the role

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that, well, everyone remembers from that era.

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Ah, Jeff Spicoli. Fast Times at Ridgemont High,

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1982. The ultimate surfer stoner dude. Totally

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iconic. And the sources actually credit his character

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with helping push the word dude into mainstream

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conversation. Which is kind of amazing. But you

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get the sense he immediately wanted to distance

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himself from Spicoli. Oh, absolutely. His very

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next big role was a complete U -turn. Bad Boys,

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1983. Playing Mick O 'Brien, this really troubled

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kid. Exactly. And that's where the critics really

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started noticing him as a serious, dramatic actor.

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Got great reviews. It sort of set the template,

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you know? Yeah. Intensity, focus, diving deep

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into troubled characters. He wasn't going to

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be just Spicoli. And that intensity, it wasn't

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just on screen, was it? It started showing up

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in his life choices, connecting his roles to

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real world actions. Definitely. A prime example

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is The Falcon and the Snowman in 85. Where he

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played Andrew Dalton Lee. the real guy convicted

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of spying for the Soviets. Right. Lee got life,

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but was paroled much later in 98. Penn obviously

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had to research him, get into his head for the

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role. And then he did something pretty unconventional

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after Lee got out. Yeah, this is fascinating.

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He hired Lou as his personal assistant. Wow.

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Why? Well, the sources suggest two main reasons.

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One, sort of a thank you to Lee for letting him

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portray him. And two, a genuine belief in rehabilitation.

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Lee had done his time and Penn seemed to feel

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strongly about helping him reintegrate. It's

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this early sign of him using his influence platform

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for something directly linked to a role, but

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with real world consequences. Taking a stand,

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basically. Exactly. And that same conviction,

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maybe that same intensity, led him to step back

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from acting for a bit in the late 80s, early

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90s. Why the break? Seems he was just dissatisfied

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with the industry, the roles, maybe the sources

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mentioned that. So he decided to focus on directing

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instead. Which led to his directing debut. The

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Indian Runner, 1991. Based on a Bruce Springsteen

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song, Highway Patrolman. So he wasn't just duping

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his toe in. He was serious about directing. Very.

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It established him as someone interested in telling

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raw, character -focused stories from behind the

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camera, too. not just the leading man. So when

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he comes back to acting in the 90s, he comes

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back with a vengeance, right? This is where he

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really cements himself as a major force. Hashtag

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tag tag tag 2 .1, establishing stardom and critical

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dominance, 1990s. Oh, absolutely. The 90s are

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arguably his peak in terms of just pure acting

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dominance and transformation. Like in Carlito's

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Way. Yeah, 1993, playing that sleazy, ambitious

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lawyer, David Kleinfeld. Total transformation,

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the hair, the voice. Everything. Got a Golden

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Globe nomination for that one. Critics were raving

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about how he just embodied this corrupt character.

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But the big one, the one that really vaulted

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him into the top tier, was Dead Man Walking.

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1995. Playing Matthew Ponslet, the death row

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inmate. Racist. Murderer. Just a terrifyingly

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intense, quiet performance. His first Oscar nomination.

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Yes, and that's when Roger Ebert called him the

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most powerful actor of his generation. High praise.

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He really committed to these dark, difficult

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roles. Totally. He wasn't afraid of them, and

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he kept winning awards. Best actor at Cannes

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in 97 for She's So Lovely. Right, the romantic

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drama. Showing some range there. Exactly. And

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then another Oscar nomination just two years

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later for Sweet and Lowdown. Woody Allen's film.

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Playing the fictional jazz guitarist, Emmett

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Ray. Yeah, egotistical, kind of flawed character,

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another complex role, another nomination. He

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was just incredibly consistent. Moving between

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these really different characters, different

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styles. And all this time, he's still directing,

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too. He did The Crossing Guard in 95. And what

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was the critical take on his directing style?

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Generally focused on that same intensity, you

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know. Critics talked about a raw searching style,

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a focus on brute emotional force, very much aligned

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with his acting. Hashtag tag tag 2 .2 the Oscar

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years and genre flexibility 2000. Okay, so the

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2000s is where the Academy Awards really start

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coming in. Kicked off with his third nomination

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for I Am Sam in 2001. Playing the father with

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a developmental disability. Right. But the first

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win came a couple of years later, 2003, Mystic

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River. Ah, yes. Playing Jimmy Markham, the father

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seeking revenge after his daughter's murder.

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Incredible performance. Just raw grief and rage.

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And that one swept the board. Oscar, Golden Globe,

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Critics' Choice. He was definitely on a roll.

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And showing flexibility too, right? Wasn't 21

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grams around the same time? Same year, 2003.

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Totally different film, nonlinear, psychological

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drama. Got a BAFTA nomination for that. He was

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really operating at his peak. And then came the

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second Oscar win for a role that felt different,

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more outwardly heroic in a way. Harvey Milk in

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Milk 2008. Playing the gay rights activist and

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politician. Yeah, a massive transformation again.

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But capturing Milk's... optimism his energy his

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uh his charisma the reviews were phenomenal people

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talked about him completely disappearing into

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the role they did words like transmigration were

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used like he inhabited milk it won him the second

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best actor oscar plus the screen actors guild

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award so he's playing this iconic historically

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significant figure And around the same time,

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his directing work is also getting major recognition.

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Absolutely. Into the Wild, 2007, the biographical

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survival story. About Christopher McCandless.

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Right. And that film was a huge critical success

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for him as a director. It got him a Directors

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Guild of America nomination, which is a big deal.

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So directing wasn't just a side project. It was

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a serious parallel career track. Definitely.

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He proved he could excel on both sides of the

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camera at the highest level. So as his career

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moves into, say, the last decade or so, we see

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him shifting gears again, moving into television.

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Yeah, which is interesting. A lot of big film

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actors started doing high -profile TV around

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then. He jumped in, too. Like with The First.

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Right, 2018. That Hulu series about the first

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manned mission to Mars, he played the lead astronaut,

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Tom Haggerty. And it's funny, even then, critics

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were still bringing up... Spicoli, yeah. One

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review mentioned he was still... game to be a

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goofball that Spicoli was still in there somewhere.

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That shadow really follows him, doesn't it? Even

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in a serious sci -fi drama. Seems like it. Then

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he did another big TV role, requiring even more

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transformation, Gaslit, in 2022. Playing John

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Mitchell, Nixon's attorney general during Watergate.

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Yeah, under heavy prosthetics. A completely different

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kind of role again. Historical, political thriller.

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Shows his range is still there. But maybe the

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biggest recent shift isn't acting or directing.

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It's... Writing. It seems so. He published a

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novel in 2018, Bob Honey, who just do stuff.

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Satirical thing. And a follow up. Yep. Bob Honey

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sings Jimmy Crack Corn in 2019. And he made some

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pretty strong statements about this shift, didn't

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he? He did. Very public. Said writing would,

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quote, dominate my creative energies for the

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foreseeable future. Wow. And he said something

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about filmmaking, too. Yeah, that he no longer

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had a generic interest in making films, which

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is a pretty definitive statement from a two time

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Oscar winner and respected director. So it sounds

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like he's consciously redirecting that famous

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intensity away from film towards literature.

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And as we have to discuss his activism. Exactly.

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Which brings us to the other side of the coin,

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the personal turmoil and the headline grabbing

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activism. Right. Because you really can't talk

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about Sean Penn without talking about the volatility,

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the controversies that often ran parallel to

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his acting success. No, they're deeply intertwined,

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starting with his high -profile relationships.

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Hashtag, tag, tag, tag, 3 .1 marriages and high

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-profile relationships. Before Madonna, there

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were others, right? Elizabeth McGovern, Susan

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Sarandon. Yeah, early relationships. But the

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marriage to Madonna in 85, that really put his

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private life and his temper under a global microscope.

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They got married right around her birthday, his

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birthday. Big media event. Huge. She dedicated

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True Blue to him, called him the coolest guy

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in the universe. It was this massive celebrity

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power couple moment. But it soured pretty quickly.

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Or at least the public perception did. Well,

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the sources are clear the marriage was marked

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by conflict. Specifically, it mentions Penn's

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violent outbursts against the press. He was constantly

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clashing with paparazzi. And that led to legal

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issues, which we'll get to. But the marriage

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itself was unstable. Seems so. She filed for

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divorce in 87, then withdrew it, then filed again

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in early 89, and that time it stuck. And for

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years there were these persistent rumors and

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allegations about domestic violence. Right. That

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narrative was out there for a long time in tabloids

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and even some biographies. But Madonna addressed

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it directly later on. Crucially, yes. In 2015,

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she issued a formal statement, denied he'd ever

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struck her, called the stories completely outrageous,

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malicious, reckless, and false. So that official

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denial is a key part of the record. It complicates

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the earlier narrative significantly. Absolutely.

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Highlights how public perception and reality

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can diverge, especially with intense media scrutiny.

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After Madonna, He had a long relationship with

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Robin Wright. Very long. They were together for

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years before marrying in 96. Had two kids, Dylan

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and Hopper. But that marriage also had its share

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of ups and downs. Definitely. They actually split

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briefly in 95 before they got married. He dated

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Jewel during that time. Oh, Ray. And then after

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marrying between 2007 and 2009, it was this cycle

00:12:16.289 --> 00:12:20.730
of filing for divorce or separation, then reconciling,

00:12:20.730 --> 00:12:23.629
then filing again. Very turbulent publicly. Until

00:12:23.629 --> 00:12:25.990
it finally ended in 2010. Yeah, the divorce was

00:12:25.990 --> 00:12:28.309
finalized then. And more recently. There was

00:12:28.309 --> 00:12:32.309
Charlize Theron. From about 2013 to 2015. Lots

00:12:32.309 --> 00:12:35.470
of media buzz, engagement rumors. But she denied

00:12:35.470 --> 00:12:37.389
they were ever engaged. Right. She clarified

00:12:37.389 --> 00:12:39.710
that later. Then a brief marriage to Layla George,

00:12:39.990 --> 00:12:42.929
daughter of Vincent D 'Onofrio. Married in 2020.

00:12:43.029 --> 00:12:45.470
She filed for divorce about a year later. Finalized

00:12:45.470 --> 00:12:49.190
in 2022. So a pattern of intense but often short

00:12:49.190 --> 00:12:51.590
-lived or tumultuous relationships. Seems to

00:12:51.590 --> 00:12:53.549
be. And his current relationship, starting in

00:12:53.549 --> 00:12:56.950
2023, is with Olga Korchayeva, who is Ukrainian.

00:12:57.250 --> 00:12:59.169
Which connects directly to his recent activism

00:12:59.169 --> 00:13:02.250
focus. Interesting. Yeah, the personal and the

00:13:02.250 --> 00:13:05.009
political often seem to intersect for him. Hashtag,

00:13:05.009 --> 00:13:08.029
tag, tag, tag, 3 .2, a history of legal issues.

00:13:08.330 --> 00:13:09.750
Okay, let's talk about the legal side. Yeah.

00:13:09.809 --> 00:13:12.070
Because his temper, especially with the press,

00:13:12.250 --> 00:13:15.120
led to actual charges and even jail time. It

00:13:15.120 --> 00:13:17.240
did. There's a clear pattern, especially in the

00:13:17.240 --> 00:13:19.480
80s. Starts around 85 in Nashville. What happened

00:13:19.480 --> 00:13:22.759
there? He pled no contest to assaulting two journalists

00:13:22.759 --> 00:13:25.779
trying to photograph him and Madonna. Got fined.

00:13:25.779 --> 00:13:28.220
Just a fine. Yeah, 50 bucks each charge. But

00:13:28.220 --> 00:13:30.840
then early 86. charged with assaulting a correspondent

00:13:30.840 --> 00:13:34.720
in Macau. Then June 86, misdemeanor battery charge

00:13:34.720 --> 00:13:37.419
for allegedly hitting songwriter David Wolinsky

00:13:37.419 --> 00:13:40.179
in a nightclub. Over Madonna again. Wolinsky

00:13:40.179 --> 00:13:42.639
claimed Penn accused him of trying to kiss her.

00:13:42.779 --> 00:13:45.360
So, yeah, repeated confrontations. And these

00:13:45.360 --> 00:13:47.639
incidents eventually caught up with him. Led

00:13:47.639 --> 00:13:50.320
to jail. Right, because he was on probation from

00:13:50.320 --> 00:13:54.080
those earlier incidents. In April 87, while filming

00:13:54.080 --> 00:13:57.679
Colors, he punched an extra on set. Just punched

00:13:57.679 --> 00:14:00.279
an extra. Or apparently. That violated his probation,

00:14:00.559 --> 00:14:03.440
resulted in a 60 -day jail sentence for the assault

00:14:03.440 --> 00:14:05.500
and reckless driving. Did he serve the full time?

00:14:05.720 --> 00:14:09.200
No, he served 33 days. But still, actual jail

00:14:09.200 --> 00:14:12.039
time. A pretty serious consequence. And there's

00:14:12.039 --> 00:14:14.179
that wild story from when he was inside. Oh,

00:14:14.240 --> 00:14:16.159
the Richard Ramirez anecdote? Yeah, Penn wrote

00:14:16.159 --> 00:14:18.019
about this himself. He was in the same jail as

00:14:18.019 --> 00:14:20.409
the Night Stalker. Apparently. Ramirez recognized

00:14:20.409 --> 00:14:23.330
him, wrote him a note. And Penn's response? Classic

00:14:23.330 --> 00:14:25.669
Penn, really. Wrote back immediately saying he

00:14:25.669 --> 00:14:28.250
felt zero connection and hoped Ramirez got the

00:14:28.250 --> 00:14:31.490
gas chamber. Just blunt, harsh moral judgment.

00:14:31.710 --> 00:14:35.029
Wow. Even in jail, corresponding with a serial

00:14:35.029 --> 00:14:37.529
killer. Okay, fast forward a couple of decades.

00:14:37.850 --> 00:14:40.110
The temper issues didn't entirely disappear.

00:14:40.389 --> 00:14:43.429
No. 2009, another run -in with a photographer,

00:14:43.750 --> 00:14:46.330
Frank Madeljian. Highly publicized. What was

00:14:46.330 --> 00:14:48.549
the outcome of that one? pled no contest again

00:14:48.549 --> 00:14:51.610
to a misdemeanor in 2010, but the sentence was

00:14:51.610 --> 00:14:54.409
steeper this time. How so? 300 hours of community

00:14:54.409 --> 00:14:58.889
service and 36 hours of mandatory anger management

00:14:58.889 --> 00:15:01.789
counseling. The court was clearly trying to address

00:15:01.789 --> 00:15:03.929
the pattern. And then there's the Lee Daniels

00:15:03.929 --> 00:15:06.590
lawsuit in 2015. This seems different, more about

00:15:06.590 --> 00:15:09.070
reputation management. Exactly. Daniels made

00:15:09.070 --> 00:15:11.850
comments in an interview linking Penn to a rumored

00:15:11.850 --> 00:15:14.070
history of domestic violence while defending

00:15:14.070 --> 00:15:17.139
another actor, Terrence Howard. And Penn sued

00:15:17.139 --> 00:15:21.360
for defamation for $10 million. Yep. But the

00:15:21.360 --> 00:15:24.580
basis of the suit was very specific. Penn argued

00:15:24.580 --> 00:15:26.779
he had never been arrested for or charged with

00:15:26.779 --> 00:15:29.320
domestic violence. Ah, so focusing on the legal

00:15:29.320 --> 00:15:31.899
record, not necessarily denying any and all past

00:15:31.899 --> 00:15:34.879
behavior. Precisely. It was a strategic legal

00:15:34.879 --> 00:15:38.299
move. And it worked, in a way. How so? The suit

00:15:38.299 --> 00:15:41.259
was dropped in 2016, but only after Daniels publicly

00:15:41.259 --> 00:15:43.830
apologized and retracted the statement. Penn

00:15:43.830 --> 00:15:46.230
made his point, very forcefully, about how his

00:15:46.230 --> 00:15:48.409
past could be legally characterized. It's like

00:15:48.409 --> 00:15:50.470
that same intensity that refusal to back down

00:15:50.470 --> 00:15:52.909
was channeled from physical confrontation into

00:15:52.909 --> 00:15:55.509
legal strategy. Yeah, it's a fascinating evolution.

00:15:55.629 --> 00:15:57.850
And that same energy then gets poured into his

00:15:57.850 --> 00:16:00.450
political activism, which becomes increasingly

00:16:00.450 --> 00:16:03.190
high stakes. Right, because his activism isn't

00:16:03.190 --> 00:16:04.809
just signing petitions. He puts himself right

00:16:04.809 --> 00:16:06.990
in the middle of things, often controversially.

00:16:06.990 --> 00:16:09.370
Oh, absolutely. He goes from fighting paparazzi

00:16:09.370 --> 00:16:12.950
to, well, engaging with... presidents and warlords.

00:16:13.090 --> 00:16:15.669
It's a major shift. This really ramps up during

00:16:15.669 --> 00:16:17.870
the lead up to the Iraq war, right? With that

00:16:17.870 --> 00:16:20.009
ad in the Washington Post. Yeah. October 2002

00:16:20.009 --> 00:16:26.129
cost him a reported $56 ,000. $56 ,000 for an

00:16:26.129 --> 00:16:29.230
ad. Yep. An open letter directly to President

00:16:29.230 --> 00:16:32.049
George W. Bush urging him not to invade Iraq.

00:16:32.330 --> 00:16:34.990
What else did it say? It was pretty sharply critical,

00:16:35.190 --> 00:16:37.529
accused the administration of dismantling civil

00:16:37.529 --> 00:16:39.889
liberties, having this simplistic and inflammatory

00:16:39.889 --> 00:16:43.210
view of good and evil. Strong stuff. And he didn't

00:16:43.210 --> 00:16:45.769
just write letters. He went there. He did. Visited

00:16:45.769 --> 00:16:49.250
Iraq briefly in December 2002. Then in 2005,

00:16:49.409 --> 00:16:52.350
he went to Iran. As an actor? No, as a journalist.

00:16:52.529 --> 00:16:54.309
Okay. For the San Francisco Chronicle, attended

00:16:54.309 --> 00:16:56.429
a Friday prayer service at Tehran University.

00:16:56.669 --> 00:16:59.049
He was embedding himself. Of course, this kind

00:16:59.049 --> 00:17:01.870
of high -profile celebrity activism invites parody.

00:17:02.299 --> 00:17:05.359
Right. Team Angarica, World Police, the 2004

00:17:05.359 --> 00:17:07.859
film from the South Park guys. They really went

00:17:07.859 --> 00:17:10.420
after him. Oh, yeah. Portrayed him as this naive

00:17:10.420 --> 00:17:13.920
idealist talking about Iraq having rainbow skies

00:17:13.920 --> 00:17:16.960
and rivers made of chocolate. Pure satire. And

00:17:16.960 --> 00:17:19.960
Penn's reaction was predictable. Let's just say

00:17:19.960 --> 00:17:22.599
he wasn't amused. wrote this furious letter back

00:17:22.599 --> 00:17:25.440
to Trey Parker and Matt Stone, sarcastically

00:17:25.440 --> 00:17:27.799
invited them to tour Iraq with him, basically

00:17:27.799 --> 00:17:29.859
told them off. He doesn't take criticism lightly.

00:17:30.059 --> 00:17:32.160
Not at all. And his own political language was

00:17:32.160 --> 00:17:35.359
often just as harsh. He called Dick Cheney and

00:17:35.359 --> 00:17:38.420
Condoleezza Rice villainously and criminally

00:17:38.420 --> 00:17:41.619
obscene people. So not exactly diplomatic. No.

00:17:41.720 --> 00:17:45.019
He was using his platform to voice really strong,

00:17:45.160 --> 00:17:48.559
often inflammatory opposition. But at the same

00:17:48.559 --> 00:17:50.539
time, he was also getting involved in hands -on

00:17:50.539 --> 00:17:53.519
humanitarian work. Yeah. Like after Hurricane

00:17:53.519 --> 00:17:56.240
Katrina. Yeah, September 2005, he went down to

00:17:56.240 --> 00:17:58.400
New Orleans. The sources say he was physically

00:17:58.400 --> 00:18:00.720
involved in rescues, pulling people from flooded

00:18:00.720 --> 00:18:03.359
homes. But that effort drew criticism too, didn't

00:18:03.359 --> 00:18:06.460
it? The whole PR stunt accusation. It did. Because

00:18:06.460 --> 00:18:08.819
he had a photographer with him. Critics questioned

00:18:08.819 --> 00:18:11.099
his motives. How did he respond? He wrote an

00:18:11.099 --> 00:18:13.730
article for HuffPost defending himself. Denied

00:18:13.730 --> 00:18:16.450
it was a stunt, said it was genuine aid. But

00:18:16.450 --> 00:18:19.349
it shows that dilemma, right? Can a celebrity

00:18:19.349 --> 00:18:21.890
do good work without it being seen through the

00:18:21.890 --> 00:18:24.069
lens of fame? A constant challenge for famous

00:18:24.069 --> 00:18:27.390
activists. But his efforts became much more organized

00:18:27.390 --> 00:18:30.490
after the Haiti earthquake in 2010. Massively

00:18:30.490 --> 00:18:33.490
so. That's when he founded JP Haitian Relief

00:18:33.490 --> 00:18:36.359
Organization, JPHRO. And this wasn't just writing

00:18:36.359 --> 00:18:38.960
a check. No, this was a huge operational commitment.

00:18:39.119 --> 00:18:42.160
They ran a camp for like 55 ,000 displaced people.

00:18:42.519 --> 00:18:45.619
He was very hands -on, very visible there for

00:18:45.619 --> 00:18:47.500
a long time. To the point where he got an official

00:18:47.500 --> 00:18:51.200
title. Yeah, this is remarkable. In 2012, Haiti's

00:18:51.200 --> 00:18:53.599
President Michel Martelly appointed him ambassador

00:18:53.599 --> 00:18:56.180
at large for Haiti. Ambassador at large. The

00:18:56.180 --> 00:18:58.660
first non -Haitian citizen ever to hold that

00:18:58.660 --> 00:19:01.460
diplomatic role. Shows the depth of his commitment

00:19:01.460 --> 00:19:04.190
there. And that work evolved into CORE. Right.

00:19:04.269 --> 00:19:07.349
Community organized relief effort. CORE expanded

00:19:07.349 --> 00:19:09.990
beyond Haiti, became very active during the COVID

00:19:09.990 --> 00:19:12.230
pandemic in the U .S., setting up free testing

00:19:12.230 --> 00:19:14.990
sites. So significant logistical and humanitarian

00:19:14.990 --> 00:19:18.190
work. Right. But even CORE faced some controversy.

00:19:18.230 --> 00:19:20.710
It did, specifically around labor issues. What

00:19:20.710 --> 00:19:23.289
happened? In late 2021, the National Labor Relations

00:19:23.289 --> 00:19:27.069
Board, the NLRB, filed a complaint. Against Penn

00:19:27.069 --> 00:19:30.779
and CORE. Yes. Alleging that Penn had... impliedly

00:19:30.779 --> 00:19:32.819
threatened employees. Threatened them for what?

00:19:32.960 --> 00:19:35.500
For complaining about working conditions. The

00:19:35.500 --> 00:19:37.980
complaint mentioned demands for 18 -hour workdays

00:19:37.980 --> 00:19:40.660
during the intense COVID response period. So

00:19:40.660 --> 00:19:42.720
that same intensity he applies to everything

00:19:42.720 --> 00:19:45.660
else maybe created issues within his own organization.

00:19:46.059 --> 00:19:48.119
That's what the complaint suggests. That the

00:19:48.119 --> 00:19:50.559
demanding all -consuming approach might have

00:19:50.559 --> 00:19:53.119
clashed with standard labor practices and worker

00:19:53.119 --> 00:19:56.480
protections. Hashtag tag tag 4 .3 controversial

00:19:56.480 --> 00:19:59.000
global alignments. Okay, this is where things

00:19:59.000 --> 00:20:01.140
get really complex. His alignments with certain

00:20:01.140 --> 00:20:04.140
world leaders, especially considering his progressive

00:20:04.140 --> 00:20:07.079
image from rolls like milk. Yeah, this is probably

00:20:07.079 --> 00:20:09.359
the most pointed area of contradiction for many

00:20:09.359 --> 00:20:12.240
observals. His friendship with Hugo Chavez, the

00:20:12.240 --> 00:20:14.700
late president of Venezuela. Chavez was known

00:20:14.700 --> 00:20:17.680
for his anti -U .S. stance, but also for increasingly

00:20:17.680 --> 00:20:21.220
authoritarian moves. Right. But Chavez publicly

00:20:21.220 --> 00:20:24.460
praised Penn, read his anti -Bush letter on TV,

00:20:24.660 --> 00:20:27.279
and Penn became a staunch defender of Chavez.

00:20:27.359 --> 00:20:29.480
To the point of defending his regime against

00:20:29.480 --> 00:20:33.670
criticism. Very much so. Famously, in 2010, Penn

00:20:33.670 --> 00:20:35.829
called for journalists who called Chavez a dictator

00:20:35.829 --> 00:20:38.880
to be jailed. Jailed. For calling a leader a

00:20:38.880 --> 00:20:40.880
dictator. That's what he said. And when Chavez

00:20:40.880 --> 00:20:43.140
died, Penn called him a global champion for the

00:20:43.140 --> 00:20:45.619
poor. Unwavering support. And he also met with

00:20:45.619 --> 00:20:48.599
Raul Castro in Cuba. Interviewed him in 2008.

00:20:48.980 --> 00:20:51.440
So the core criticism here is. The clash with

00:20:51.440 --> 00:20:54.099
his image as a champion of rights, especially

00:20:54.099 --> 00:20:57.519
LGBTQ plus rights given milk. Both the Chavez

00:20:57.519 --> 00:21:00.420
and Castro regimes had poor records on LGBTQ

00:21:00.420 --> 00:21:03.039
plus issues. How did the sources explain this?

00:21:03.099 --> 00:21:05.279
Does he address the contradiction? Not directly

00:21:05.279 --> 00:21:08.380
in the materials we reviewed. It seems for Penn,

00:21:08.599 --> 00:21:11.660
maybe the anti -imperialist stance or the focus

00:21:11.660 --> 00:21:14.579
on poverty alleviation in those specific relationships

00:21:14.579 --> 00:21:18.400
took precedence over alignment on social issues.

00:21:18.640 --> 00:21:21.619
He seems to compartmentalize his alliances. Willing

00:21:21.619 --> 00:21:24.740
to overlook certain aspects for a perceived greater

00:21:24.740 --> 00:21:27.619
good, perhaps? Perhaps. Or maybe he just saw

00:21:27.619 --> 00:21:29.519
those leaders differently than their critics

00:21:29.519 --> 00:21:32.019
did. It's hard to say definitively from the outside.

00:21:32.279 --> 00:21:35.009
But the contradiction is stark. And then came

00:21:35.009 --> 00:21:36.769
maybe the most controversial meeting of all,

00:21:37.430 --> 00:21:40.450
El Chapo. Yeah, 2016. While Joaquin El Chapo

00:21:40.450 --> 00:21:42.569
Guzman, the head of the Sinaloa cartel, was a

00:21:42.569 --> 00:21:45.150
fugitive, Penn secretly met him. How did that

00:21:45.150 --> 00:21:47.809
even happen? It was brokered by the Mexican actress,

00:21:48.029 --> 00:21:50.289
Kite Del Castillo. The goal was an interview

00:21:50.289 --> 00:21:52.710
for Rolling Stone. And the details were just...

00:21:53.329 --> 00:21:56.490
Bizarre. Totally. Leaked texts later suggested

00:21:56.490 --> 00:21:58.650
El Chapo barely knew who PIN was. He was more

00:21:58.650 --> 00:22:00.509
interested in Caita Castillo. What was the official

00:22:00.509 --> 00:22:02.970
reaction? Not good. The White House called the

00:22:02.970 --> 00:22:05.869
interview maddening, said it potentially interfered

00:22:05.869 --> 00:22:08.809
with efforts to capture Guzman. Did PIN face

00:22:08.809 --> 00:22:11.490
legal trouble over it? Mexican authorities investigated,

00:22:11.809 --> 00:22:14.410
wanted to question him. It was a major international

00:22:14.410 --> 00:22:17.289
incident, blurring the lines between journalism,

00:22:17.589 --> 00:22:20.690
activism and, well, associating with one of the

00:22:20.690 --> 00:22:23.109
world's most wanted criminals. It really demonstrates

00:22:23.109 --> 00:22:26.769
his willingness to operate way outside conventional

00:22:26.769 --> 00:22:29.670
boundaries. No fear of the risk, it seems. None

00:22:29.670 --> 00:22:32.390
whatsoever, which we also saw maybe less dramatically,

00:22:32.470 --> 00:22:34.630
but still controversially with the Falklands

00:22:34.630 --> 00:22:37.640
issue. Right. 2012. meeting with Argentina's

00:22:37.640 --> 00:22:39.740
president, Cristina Fernandez de Kirchner. And

00:22:39.740 --> 00:22:42.640
he wades right into the sovereignty dispute with

00:22:42.640 --> 00:22:45.660
the UK over the Falkland Islands, or Malvinas,

00:22:45.680 --> 00:22:47.599
as Argentina calls them. What exactly did he

00:22:47.599 --> 00:22:50.339
say? He talked about opposing ridiculous demonstrations

00:22:50.339 --> 00:22:53.259
of colonialism and pushed for dialogue. Which

00:22:53.259 --> 00:22:55.579
predictably caused outrage in Britain. Oh, yeah.

00:22:55.859 --> 00:22:58.480
British tabloids and politicians slammed him,

00:22:58.559 --> 00:23:01.240
called his comments moronic. Did he walk it back?

00:23:01.720 --> 00:23:04.700
He clarified later, said his comments were misrepresented,

00:23:04.759 --> 00:23:07.339
that he was really criticizing Prince William's

00:23:07.339 --> 00:23:10.980
military deployment there as preemptive intimidation.

00:23:11.000 --> 00:23:14.200
He framed it as opposing militarism, advocating

00:23:14.200 --> 00:23:17.140
for diplomacy and negotiation, even suggesting

00:23:17.140 --> 00:23:19.940
things like immigration changes. Hashtag hashtag

00:23:19.940 --> 00:23:23.599
4 .4 advocacy and conflict in Ukraine. So that

00:23:23.599 --> 00:23:25.720
brings us to his most recent and perhaps most

00:23:25.720 --> 00:23:29.450
sustained geopolitical focus. Ukraine. Right.

00:23:29.750 --> 00:23:32.190
This seems to be where a lot of his energy has

00:23:32.190 --> 00:23:35.029
been directed lately. He was there in 2022 filming

00:23:35.029 --> 00:23:37.990
a documentary. Superpower. profiling president

00:23:37.990 --> 00:23:41.210
zielinski exactly he was embedded meeting officials

00:23:41.210 --> 00:23:44.130
attending briefings right up close and he was

00:23:44.130 --> 00:23:45.930
actually there when the full -scale invasion

00:23:45.930 --> 00:23:49.029
began he was which led to that incredible story

00:23:49.029 --> 00:23:50.970
of him and his team having to abandon their car

00:23:50.970 --> 00:23:53.230
and walk for miles to the polish border to get

00:23:53.230 --> 00:23:55.910
out that's intense real personal risk absolutely

00:23:55.910 --> 00:23:57.750
and his statements afterwards were completely

00:23:57.750 --> 00:24:00.190
unambiguous total support for ukraine like that

00:24:00.190 --> 00:24:02.759
quote about america losing its soul If we allow

00:24:02.759 --> 00:24:06.400
Ukraine to fight alone, our soul as America is

00:24:06.400 --> 00:24:10.180
lost. Very strong words. Led to Russia sanctioning

00:24:10.180 --> 00:24:12.299
him, putting him on their blacklist. And then

00:24:12.299 --> 00:24:15.119
came that symbolic gesture in Kyiv. The Oscar

00:24:15.119 --> 00:24:18.819
loan. November 2022. Yeah. He physically gave

00:24:18.819 --> 00:24:21.640
one of his Oscar statuettes to President Zelensky.

00:24:21.740 --> 00:24:23.599
What was the condition? When you win, bring it

00:24:23.599 --> 00:24:26.559
back to Malibu. Just the simple, powerful symbol

00:24:26.559 --> 00:24:29.240
of faith and solidarity. And Zelensky gave him

00:24:29.240 --> 00:24:31.779
something in return. The Ukrainian Order of Merit,

00:24:31.799 --> 00:24:34.140
a formal state honor. It really cemented his

00:24:34.140 --> 00:24:36.460
role as a high profile international advocate

00:24:36.460 --> 00:24:39.099
for Ukraine's cause. It's quite an image. The

00:24:39.099 --> 00:24:43.180
Hollywood Award traded temporarily for a wartime

00:24:43.180 --> 00:24:45.920
medal. It encapsulates so much about him. Hashtag

00:24:45.920 --> 00:24:47.759
tag outro. It really does. When you look back

00:24:47.759 --> 00:24:49.500
at everything we've covered, that duality is

00:24:49.500 --> 00:24:52.259
just. It's inescapable. You have this incredible

00:24:52.259 --> 00:24:54.839
actor capable of these deep, transformative,

00:24:55.019 --> 00:24:58.160
award -winning performances. Mystic River, Milk,

00:24:58.480 --> 00:25:01.220
Dead Man Walking. Intense commitment to the craft.

00:25:01.380 --> 00:25:03.259
But then you have the other Sean Penn, the activist.

00:25:03.619 --> 00:25:06.079
Volatile, yes, but also deeply engaged, willing

00:25:06.079 --> 00:25:08.779
to dive headfirst into incredibly complex, dangerous

00:25:08.779 --> 00:25:11.680
situations. Katrina rescues, building camps in

00:25:11.680 --> 00:25:14.319
Haiti, the Chavez friendship, the El Chapo meeting,

00:25:14.519 --> 00:25:17.319
walking out of Ukraine. It's the same intensity

00:25:17.319 --> 00:25:19.819
applied in radically different arenas. Those

00:25:19.819 --> 00:25:21.880
leading to acclaim, sometimes to controversy,

00:25:22.160 --> 00:25:25.400
sometimes to legal trouble. Exactly. So for you

00:25:25.400 --> 00:25:27.579
listening, the key takeaway is that this commitment,

00:25:27.680 --> 00:25:30.339
this intensity is the engine driving both the

00:25:30.339 --> 00:25:32.819
artistic triumphs and the real world controversies.

00:25:32.819 --> 00:25:35.200
You can't really separate them. He's resisted

00:25:35.200 --> 00:25:38.059
simple labels his entire career. And we saw how

00:25:38.059 --> 00:25:40.299
he won his highest acting honors portraying a

00:25:40.299 --> 00:25:43.220
celebrated gay rights hero in Milk. But then

00:25:43.220 --> 00:25:46.339
he strongly defended. leaders like Chavez and

00:25:46.339 --> 00:25:49.339
Castro, whose governments had documented anti

00:25:49.339 --> 00:25:52.299
-LGBT policies. That's the central paradox, isn't

00:25:52.299 --> 00:25:54.619
it? It really is. And it leaves us with a question

00:25:54.619 --> 00:25:56.779
to think about. In today's world, with constant

00:25:56.779 --> 00:25:59.539
scrutiny, can this kind of intense, sometimes

00:25:59.539 --> 00:26:02.180
contradictory celebrity activism function effectively

00:26:02.180 --> 00:26:05.740
in the gray areas of global politics? Or is it

00:26:05.740 --> 00:26:08.279
always going to be defined and maybe judged by

00:26:08.279 --> 00:26:10.740
its most glaring inconsistencies? Something to

00:26:10.740 --> 00:26:11.079
ponder.
