WEBVTT

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Welcome back to the Deep Dive. We pull the threads,

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track the chronology, and really try to tell

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the full story of people whose careers just refuse

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to be simple. Exactly. And today... We are undertaking

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a deep dive into the, well, fascinating, definitely

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two -sided professional life of Jason Segel.

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Yeah, for a whole generation, he is absolutely

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Marshall Erickson. Yeah. You know, the giant,

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lovable sweetheart from How I Met Your Mother.

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A totally iconic role. But, like, if you only

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know that version of him, you're missing so much

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of the picture. Right. We're going to trace his

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path from, you know, being one of Judd Apatow's

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original freaks all the way to becoming an Emmy

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nominated showrunner, a critically acclaimed

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dramatic lead. I mean, he played. David Foster

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Wallace. Which is just incredible casting when

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you think about it. And a surprisingly successful

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young adult novelist, too. It's quite the range.

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That's absolutely right. So our mission today

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is basically to pore over all the details of

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this, what, 25 -plus year journey starting way

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back in the late 90s and pinpoint exactly how

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he kind of engineered his own creative independence.

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Because if you, the listener, are curious about

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the mechanics of moving from, like, massive,

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defining mainstream success into really serious,

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critical acclaim. Well, this deep dive kind of

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shows you the blueprint. It really proves that

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the surest way to beat typecasting is, well...

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to write your own way out. It's definitely a

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study in leveraging vulnerability maybe into

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creative capital, you know? Yeah. And to really

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understand the sophisticated creator he is now,

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we have to start right at the beginning with

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a childhood that seems to have instilled this

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really profound sense of observation. Okay, so

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Siegel. Born 1980, Santa Monica, California.

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Grew up in Pacific Palisades, which is pretty

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affluent. Right. On the surface, that sounds

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like, you know, a pretty standard Southern California

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actor origin story. Kind of, yeah. But you dig

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just a little deeper. And his family, his educational

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background, it created this really complex identity.

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Okay, tell us about that. Well, what seems genuinely

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foundational here is this idea of duality that

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really marked his upbringing. Duality, how so?

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So his father, Alvin Siegel, he's a lawyer. and

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jewish his mother jillian jordan she comes from

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this rich blend of like english scottish irish

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and french heritage okay and siegel when he's

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interviewed he often kind of jokes he was raised

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a little bit of everything but he does confirm

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his jewish upbringing went to hebrew school had

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a bar mitzvah all that but the sources we looked

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at suggest the real The core conflict maybe wasn't

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inside his home. It was more external. Yeah.

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Driven by his schooling. Exactly. He went to

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St. Matthew's Parish School, which is, you know,

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a very exclusive private Episcopal school. Right.

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While simultaneously attending Hebrew school

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at night. Wow. OK. That must have created like

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a profound sociological challenge for a young

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kid. Oh, absolutely. The sources really detail

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how the split environment fed into this intense

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sense of being an outsider. You know, he wasn't

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fully integrated. into either social structure.

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He apparently felt like the Jewish kid at the

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Christian school, you know, watching the rituals

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and dynamics he wasn't totally part of. And then

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the reverse at Hebrew school. And conversely,

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yeah, he felt like the kid with the Christian

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school background when he was at Hebrew school.

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So what was the emotional result of constantly

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having to compartmentalize like that? Well, he's

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admitted this feeling of social alienation. It

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led him to adopt this kind of it's me versus

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the world survival mechanism. And this is key,

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I think, because that slightly alienated, you

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know, highly sensitive, empathetic observer,

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that's exactly the kind of character he would

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later embody so well. Right. You see it in Nick

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Andopoulos. Totally. Nick Andopoulos, Marshall

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Erickson. even decades later that anxious therapist

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jimmy laird in shrinking he basically learned

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to watch which is i mean crucial training for

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both acting and writing okay but before he fully

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embraced that you know sensitive writer persona

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yeah he was something completely different like

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startlingly different oh yeah a genuine serious

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athlete let's talk about this incredible juxtaposition

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of dr dunk this is truly one of the most like

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unexpected nuggets in his whole biography jason

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siegel is tall right six foot four very tall

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and that size was definitely leveraged during

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his high school years at harvard westlake school

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and we're talking about a serious basketball

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program there okay he was an active Pretty valuable

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member of the boys basketball team that won the

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CIF state championship title. Not just once,

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but twice. In 96 and 97. You hear Harvard -Westlake,

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CIF state champion. I mean, that implies real

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dedication, serious skill. Oh, yeah. But the

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nickname is what really makes this era kind of

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pop. He wasn't just like riding the bench. He

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earned the nickname Dr. Dunk. Because he actually

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won a high school slam dunk contest. I know.

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Can you even picture like the Nick Andopolis

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character? No. Or Marshall Erickson executing

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some championship winning slam dunk. It's just

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a hilarious mental image. It totally contradicts

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his whole acting vibe later on. Completely. It

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speaks to this kind of hidden physical discipline

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and athleticism that maybe informs his presence,

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even if his characters are often, you know, goofy

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or kind of clumsy. And here's a fascinating little

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piece of trivia that really places him right

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in the middle. of this high -level competition.

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He was the backup center to Jason Collins. No

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way. Yeah, who later went on to have a long,

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successful career in the NBA. Wow. Okay, so he

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was playing with serious talent. Definitely.

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This athletic history, it just grounds him in

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a world so far... removed from the dramatic arts,

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it provides a surprising depth to his background,

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I think. Yeah, for sure. But that athletic discipline,

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it pretty quickly gave way to artistic pursuits,

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which brings us right to the Apatow launchpad.

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Right. After high school, his first major role

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really defined that whole era of cult TV. Nick

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Andopoulos on the, you know, beloved but very

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short -lived Freaks and Geeks. That was 99 to

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2000. He was the stoner freak with the drum set.

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And it's so important to remember that Freaks

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and Geeks, even though it got canceled way too

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fast. Way too fast. It really established the

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core philosophy that seems to have fueled his

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entire career. A whole Apatow ethos. Totally.

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That ethos built on improv, honesty, and just

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translating personal experience directly into

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the material. And Siegel seemed to buy into that,

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like, immediately. Oh, completely. What sets

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him apart, maybe, from many of his co -stars

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in that series, even that early on, is that he

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didn't just wait for the script to tell him what

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Nick should do. Right. The sources confirm he

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actually personally composed a song for Nick

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Andopoulos to sing to the lead female character,

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Lindsay. Played by Linda Cardellini. Played by

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Linda Cardellini, who he actually ended up dating

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later in real life. Right, right. But that song,

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that's a foundational moment, isn't it, of creative

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ownership? Absolutely. That song, it's just this

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small, touching, kind of awkward piece of music.

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But it was his first produced work as a writer

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within a major Hollywood production. It wasn't

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planned. He contributed it. And that decision

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to actively create and contribute, that just

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became the signature move of his career, really.

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It did. Even after Freaks and Geeks got the axe,

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he kept that crucial relationship with Judd Apatow

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going, appeared in recurring roles on Apatow's

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next series, Undeclared. Got some early film

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experience and stuff like Can't Hardly Wait back

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in 98, SLC Punk. Right. He was clearly just marinated

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in that Apatow philosophy. Vulnerability equals

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humor. And if you make the material yourself,

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that's gold. OK, so this Apatow training, it

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totally set the stage for the role that would

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define him for like an entire decade. Marshall

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Erickson. Marshall Erickson on How I Met Your

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Mother. The stability of that role is just. It's

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remarkable, really. He was the main character

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for 208 episodes, spanning nine seasons from

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2005 all the way to 2014. I mean, for an actor

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getting a role that lasts nearly 10 years. That's

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like the brass ring of Hollywood success. Huge

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financial stability, massive household recognition.

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But professional stability often comes with that

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risk, right, of artistic stagnation. Yeah. And

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it's important to look at the timeline here.

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The source material we have notes he actually

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reached a point where he felt he needed to break

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free. He absolutely did. By 2013, you know, when

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his contract was running out, he had publicly

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stated his intention to move on. Yeah. He was

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clearly feeling the pull of like the characters

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and stories he wanted to write. rather than just

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playing the one he'd inherited, I guess. So how

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did they keep him for that last season? Well,

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it apparently took a pretty significant effort

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from the producers to convince him to come back

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and finish out the ninth and final season in

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2014, which kind of demonstrates both things,

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right? His enormous value to the show, but also

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his really powerful desire for creative evolution

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by that point. And that push for creative evolution,

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it had actually started much earlier, like right

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in the middle of his HIM run. Yeah. During in

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Knocked Up in 2007, his massive breakthrough

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moment really happened in 2008 with Forgetting

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Sarah Marshall. And this film wasn't just a hit.

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It felt like his declaration of independence.

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Precisely. This is really the moment Siegel transitions

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from being like Apatow's Atlantis to his creative

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partner. Right. Apatow produced it, sure. But

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Siegel wrote the screenplay and starred as Peter

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Bretter. He basically took everything he'd learned

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about writing from personal pain. And put it

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directly onto the screen. And this is where we

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get into some of the infamous deep dive anecdotes

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because the personal translation here is just

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extraordinary. Oh, yeah. The source has confirmed

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that the two most memorable. kind of painful

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plot points in the film were rooted in his actual

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life okay so the first one is that puppet musical

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about dracula right which his character peter

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is desperately trying to stage yes the dracula

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musical hilarious and the second is that iconic

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scene involving a full frontal male nudity right

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after a breakup right he leveraged his most vulnerable

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maybe humiliating experiences and just turned

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them straight into comedy i mean think about

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it how many actors would willing script the scene

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where they get dumped while totally naked just

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because it actually happened to them? It's bravery.

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Or maybe, like you said, sheer desperation. Yeah.

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But it's an incredible act of creative honesty,

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whatever it is. It's kind of the highest form

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of that Apatow -era comedy, isn't it? Siegel

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confirmed in interviews, yeah, he was indeed

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broken up with while naked, which became the

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sort of emotional foundation for Peter Bretter's

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despair in the movie. And the Dracula musical.

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Was that just a funny bit? Apparently not just

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invented for the screen. he later actually performed

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dracula's lament live on the late late show with

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craig ferguson no way yeah showing how committed

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he really was to the sincerity of that like creative

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outlet this film just demonstrated that his unique

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blend of sensitivity and well vulgarity yeah

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combined with that willingness to write his own

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stuff That was a massive market asset. And that

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Dracula musical, weirdly enough, actually became

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the launch pad for a complete tonal shift in

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his career. Yeah. The Muppets Connection. It

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is truly one of the most fascinating career pivots

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I think we've ever seen. How did that happen?

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Well, the custom -made cloth creatures they used

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for the musical in Forgetting Sarah Marshall,

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they were provided by the Jim Henson Company.

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Ah, all right. And that experience, working with

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them, it immediately emboldened Siegel to do

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what seemed kind of impossible, pitch Disney.

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on a full -blown Muppets revival movie. Okay,

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but how did he possibly convince Disney, like

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the biggest family studio in the world, to hand

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over one of their most beloved IPs to the guy

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who had literally just exposed himself full frontal

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on screen? That seems like an impossible tonal

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shift bridge. It apparently required genuine

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passion and a lot of sincerity. Disney was understandably

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pretty hesitant because of the, you know, recent

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FSM nudity. You'd think. But Siegel approached

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it with this almost like religious devotion.

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His motivation was intensely personal. He said

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he was genuinely concerned that the younger generation

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was growing up without knowing the magic of the

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Muppets. Because the last movie had been ages

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ago. Exactly. The last theatrical release was

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Muppets from Space way back in 1999. So he basically

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sold them on nostalgia and like. being a guardian

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of the brand, proving he wasn't trying to make

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some raunchy Muppet film, but a sincere heartfelt

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tribute. That seems to be it. He wrote it, he

00:12:34.720 --> 00:12:36.639
executive produced it, and he starred in The

00:12:36.639 --> 00:12:39.200
Muppets in 2011 as Gary. And it was huge, right?

00:12:39.440 --> 00:12:42.360
Huge critical and commercial success. A real

00:12:42.360 --> 00:12:45.700
triumph of passion over maybe prior reputation.

00:12:46.220 --> 00:12:48.379
It earned him a Critics' Choice Award for Best

00:12:48.379 --> 00:12:50.879
Song. Wow. Demonstrating his triple threat status

00:12:50.879 --> 00:12:54.700
again. Writer, star, musician. The whole experience

00:12:54.700 --> 00:12:56.740
just confirmed that when Siegel writes the material,

00:12:57.019 --> 00:12:59.620
the opportunities just multiply like crazy. Okay,

00:12:59.659 --> 00:13:03.570
so... The early 2010s, this period saw his comedy

00:13:03.570 --> 00:13:06.230
film run just absolutely explode. He was clearly

00:13:06.230 --> 00:13:09.450
leveraging that new powerful status as a writer

00:13:09.450 --> 00:13:11.470
star. Prolific is definitely the word. He co

00:13:11.470 --> 00:13:13.549
-starred with Paul Rudd in I Love You Man in

00:13:13.549 --> 00:13:16.730
2009, playing the iconic Sidney Fife. Their chemistry

00:13:16.730 --> 00:13:18.549
was great. Loved that movie. Yeah, it was fun.

00:13:18.710 --> 00:13:21.610
He was also in Bad Teacher in 2011. And continuing

00:13:21.610 --> 00:13:23.990
his writing streak, he penned and starred in

00:13:23.990 --> 00:13:26.250
the five -year engagement in 2012 alongside Emily

00:13:26.250 --> 00:13:28.730
Blunt. Right. And then he rounded out that kind

00:13:28.730 --> 00:13:31.190
of era with a role in... And this is 40 in 2012.

00:13:31.370 --> 00:13:34.230
Back with Apatow. And we can't forget his successful

00:13:34.230 --> 00:13:36.210
dip into voice acting during this time, too,

00:13:36.289 --> 00:13:38.809
which added another massive family franchise

00:13:38.809 --> 00:13:41.950
to his resume. Oh, yeah. He voiced Gru's arch

00:13:41.950 --> 00:13:45.950
rival, the spectacularly arrogant Vector Perkins

00:13:45.950 --> 00:13:49.330
in Despicable Me. Vector. Oh, yeah. Exactly.

00:13:49.529 --> 00:13:52.230
That was 2010. Immensely successful animated

00:13:52.230 --> 00:13:54.649
film. And it wasn't just a one off gig either.

00:13:54.710 --> 00:14:08.179
That role has had. Wow. OK, so Vector lives on.

00:14:08.240 --> 00:14:10.580
Vector lives on. It's clear Siegel was pushing

00:14:10.580 --> 00:14:12.659
himself creatively just through sheer volume

00:14:12.659 --> 00:14:15.360
during this period. But like we noted, creative

00:14:15.360 --> 00:14:18.139
control comes with risk. We kind of have to examine

00:14:18.139 --> 00:14:21.100
Sex Take, the 2014 film he co -wrote and executive

00:14:21.100 --> 00:14:24.019
produced. Yeah. This was definitely not the critical

00:14:24.019 --> 00:14:26.730
darling that, say, Sarah Marshall or the Muppets

00:14:26.730 --> 00:14:29.389
were. No, it wasn't. And this is a really crucial

00:14:29.389 --> 00:14:32.370
pivot point to analyze maybe the downside of

00:14:32.370 --> 00:14:34.529
that creative ownership. Sextate came out with

00:14:34.529 --> 00:14:36.429
pretty high expectations, I think. Yeah. Big

00:14:36.429 --> 00:14:38.470
stars. Interesting premise. But it just fell

00:14:38.470 --> 00:14:40.850
flat critically. It earned him shared Razzie

00:14:40.850 --> 00:14:43.889
nominations in 2015 for worst screen combo with

00:14:43.889 --> 00:14:46.409
Cameron Diaz and also for worst screenplay. Ouch.

00:14:46.830 --> 00:14:49.470
Razzie's. Yeah. This isn't just a minor flop.

00:14:49.649 --> 00:14:51.769
It kind of signals the challenges of translating

00:14:51.769 --> 00:14:55.149
his particular style, which really thrives. on

00:14:55.149 --> 00:14:58.629
that sincere vulnerability into more of a high

00:14:58.629 --> 00:15:01.809
concept, maybe farcical commercial comedy. So

00:15:01.809 --> 00:15:04.909
what went wrong there? Was it just like genre

00:15:04.909 --> 00:15:08.389
fatigue or did the material maybe feel less personal,

00:15:08.429 --> 00:15:11.049
less earned compared to his earlier writing?

00:15:11.230 --> 00:15:13.230
It seems like maybe a combination of things.

00:15:13.289 --> 00:15:16.399
Sex tape had an interesting premise, sure. But

00:15:16.399 --> 00:15:19.340
perhaps that inherent personal honesty of Siegel's

00:15:19.340 --> 00:15:21.639
writing style, the thing that powered forgetting

00:15:21.639 --> 00:15:24.179
Sarah Marshall. Right. Maybe it got diluted by

00:15:24.179 --> 00:15:27.120
trying to fit it into a more classic, broad studio

00:15:27.120 --> 00:15:29.659
comedy structure. I don't know. Yeah, I do. But

00:15:29.659 --> 00:15:32.200
it serves as a necessary reminder, I guess, that

00:15:32.200 --> 00:15:34.059
creative control is a double edged sword. When

00:15:34.059 --> 00:15:36.240
you take full credit, you got to take full responsibility

00:15:36.240 --> 00:15:39.159
for the lows, too, not just the highs. And critically,

00:15:39.419 --> 00:15:41.899
this moment, this reception, it seems to have

00:15:41.899 --> 00:15:44.039
really solidified his decision to drastically

00:15:44.039 --> 00:15:46.379
redefine his career path. right after. Yeah,

00:15:46.399 --> 00:15:48.519
that Razzie nomination really feels like the

00:15:48.519 --> 00:15:51.039
definitive marker, doesn't it? Closing the chapter

00:15:51.039 --> 00:15:53.679
on that early 2010s mainstream comedy hustle.

00:15:53.919 --> 00:15:56.820
It seems like it. Because Siegel pivoted, like,

00:15:56.899 --> 00:15:59.840
entirely, signaling he was ready to shed that

00:15:59.840 --> 00:16:02.659
label of just the funny tall guy and really demand

00:16:02.659 --> 00:16:05.620
serious dramatic attention. And this pivot, it

00:16:05.620 --> 00:16:10.179
centers completely on one film, the 2015 independent

00:16:10.179 --> 00:16:13.340
biographical drama The End of the Tour. Right.

00:16:13.799 --> 00:16:15.639
Playing David Foster Wallace. Yeah, here Siegel

00:16:15.639 --> 00:16:19.340
took on this just monumental task of portraying

00:16:19.340 --> 00:16:22.080
the late, brilliant, but also deeply anxious

00:16:22.080 --> 00:16:25.299
author David Foster Wallace, known for, you know,

00:16:25.320 --> 00:16:28.399
infinite jest. Why was DFW the perfect character,

00:16:28.399 --> 00:16:30.659
do you think, for Siegel's big, dramatic debut?

00:16:30.759 --> 00:16:32.840
It seems like such a leap. Well, maybe it was

00:16:32.840 --> 00:16:35.700
kind of a perfect storm of casting. DFW embodied

00:16:35.700 --> 00:16:38.059
that intellectual intensity, the social anxiety,

00:16:38.340 --> 00:16:41.320
that profound, complex sense of observation.

00:16:42.460 --> 00:16:44.220
All themes Siegel seems to have carried from

00:16:44.220 --> 00:16:46.399
his own outsider youth, right? Yeah, that tracks.

00:16:46.600 --> 00:16:49.139
And Siegel's physical presence too, his height,

00:16:49.240 --> 00:16:51.200
that somewhat shambling demeanor, his sensitive

00:16:51.200 --> 00:16:53.679
eyes, it all seemed to translate the author's

00:16:53.679 --> 00:16:55.980
persona really well. You know, the constant introspection

00:16:55.980 --> 00:16:59.200
kind of hidden behind the signature plaid bandana.

00:16:59.279 --> 00:17:01.419
So it wasn't just acting, it felt more like embodiment.

00:17:01.519 --> 00:17:04.059
That's what the reviews suggested, yeah. It felt

00:17:04.059 --> 00:17:06.359
like embodiment. And the industry response was

00:17:06.359 --> 00:17:10.180
pretty seismic, wasn't it? Oh, it was overwhelmingly

00:17:10.180 --> 00:17:13.880
positive. Critics just lauded his ability to

00:17:13.880 --> 00:17:16.400
capture the nuance of this genius grappling with

00:17:16.400 --> 00:17:19.000
fame, anxiety, the pressure of his own intellect.

00:17:19.519 --> 00:17:22.000
Reviews in places like Roger Ebert's site, Entertainment

00:17:22.000 --> 00:17:25.130
Weekly. Richard Lawson at Vanity Fair specifically

00:17:25.130 --> 00:17:28.630
called the performance a huge breakthrough. Wow.

00:17:28.990 --> 00:17:31.730
Recognizing that Siegel had basically fundamentally

00:17:31.730 --> 00:17:34.230
reshaped his professional identity in just one

00:17:34.230 --> 00:17:36.529
film. And that breakthrough, it garnered real

00:17:36.529 --> 00:17:38.690
tangible recognition too. Right. Which is what

00:17:38.690 --> 00:17:40.769
agents and studios look for, right? Yeah. To

00:17:40.769 --> 00:17:42.970
validate that kind of career shift. Totally.

00:17:43.029 --> 00:17:45.410
He got an Independent Spirit Award nomination

00:17:45.410 --> 00:17:48.369
for Best Male Lead. Yeah. Which is highly respected,

00:17:48.549 --> 00:17:50.569
especially in the independent film world. Right.

00:17:50.609 --> 00:17:53.180
And furthermore, he placed third. for Best Actor

00:17:53.180 --> 00:17:56.359
at the Seattle International Film Festival. This

00:17:56.359 --> 00:17:58.279
performance just gave him the critical currency

00:17:58.279 --> 00:18:00.859
he needed to basically walk away from broad comedy

00:18:00.859 --> 00:18:03.359
and start choosing these highly selective dramatic

00:18:03.359 --> 00:18:07.819
roles. So with that gate opened, he really leaned

00:18:07.819 --> 00:18:11.460
into diversifying that drama portfolio. What

00:18:11.460 --> 00:18:14.180
were some of the key roles that came after End

00:18:14.180 --> 00:18:17.059
of the Tour? Well, you see him consistently choosing

00:18:17.059 --> 00:18:20.640
roles that explore, like, existential or deep

00:18:20.640 --> 00:18:23.099
emotional territory. Look at The Discovery from

00:18:23.099 --> 00:18:25.680
2017. Okay. A film dealing with the scientific

00:18:25.680 --> 00:18:28.119
proof of an afterlife and all the philosophical

00:18:28.119 --> 00:18:30.559
dilemmas that causes. Interesting. Then there's

00:18:30.559 --> 00:18:34.099
Our Friend in 2019. He plays Dane Fauchot, a

00:18:34.099 --> 00:18:36.259
character based on a real guy who moved in with

00:18:36.259 --> 00:18:38.380
his friends to help them manage a terminal illness.

00:18:38.680 --> 00:18:42.079
Oh, wow. Heavy themes, grief, sacrifice. Yeah,

00:18:42.140 --> 00:18:44.339
based on Matthew Teague's really powerful 2015.

00:18:44.680 --> 00:18:47.420
essay and he also proved his versatility by tackling

00:18:47.420 --> 00:18:51.000
the thriller genre with windfall in 2022 play

00:18:51.000 --> 00:18:53.980
the character just called nobody and again here's

00:18:53.980 --> 00:18:55.839
siegel leveraging that creative control again

00:18:55.839 --> 00:18:58.500
he was also credited as a story writer and producer

00:18:58.500 --> 00:19:00.859
on that film the pattern is just so consistent

00:19:00.859 --> 00:19:03.819
isn't it if the role is complex he wants a hand

00:19:03.819 --> 00:19:06.380
in shaping the narrative itself Seems like it.

00:19:06.420 --> 00:19:08.720
And this brings us back to television, but in

00:19:08.720 --> 00:19:10.720
a totally different context than how I met your

00:19:10.720 --> 00:19:14.099
mother. Right. He took on a really significant

00:19:14.099 --> 00:19:17.500
historical role portraying Paul Westhead. The

00:19:17.500 --> 00:19:19.319
legendary coach. Yeah. The high school coach

00:19:19.319 --> 00:19:21.740
turned Lakers coach. Yeah. In the HBO series

00:19:21.740 --> 00:19:24.259
Winning Time. The rise of the Lakers dynasty.

00:19:24.480 --> 00:19:27.339
Playing Paul Westhead for 12 episodes between

00:19:27.339 --> 00:19:31.490
2022 and 2023. I mean. Talk about a complex,

00:19:31.809 --> 00:19:34.430
driven, often misunderstood figure in basketball

00:19:34.430 --> 00:19:36.589
history. About as far as you can possibly get

00:19:36.589 --> 00:19:39.009
from Marshall Erickson. Absolutely. Reinforcing

00:19:39.009 --> 00:19:41.369
his commitment to that dramatic immersion. And

00:19:41.369 --> 00:19:43.670
that whole trajectory brings us pretty much up

00:19:43.670 --> 00:19:45.650
to his current era. Yeah. Which is maybe the

00:19:45.650 --> 00:19:48.190
culmination of all his training, the creator,

00:19:48.410 --> 00:19:51.710
the showrunner, and the nominee. Okay. He seems

00:19:51.710 --> 00:19:54.130
to have now fully synthesized his writing talent,

00:19:54.289 --> 00:19:56.970
his dramatic sensitivity, and yeah, his comedic

00:19:56.970 --> 00:19:59.250
timing too, into creating original television

00:19:59.250 --> 00:20:01.670
series. His first big push into this space was

00:20:01.670 --> 00:20:04.509
Dispatches from Elsewhere back in 2020. What

00:20:04.509 --> 00:20:06.950
was the vision behind that show? It felt different.

00:20:07.230 --> 00:20:10.390
It was pure auteur television, really. He created

00:20:10.390 --> 00:20:12.509
it, starred in it, wrote for it, directed episodes,

00:20:12.769 --> 00:20:15.109
and executive produced all 10 episodes. Wow.

00:20:15.329 --> 00:20:19.450
Full control. Total control. The show... which

00:20:19.450 --> 00:20:23.170
explored these ordinary people solving this kind

00:20:23.170 --> 00:20:26.960
of esoteric strange puzzle it felt like a surreal

00:20:26.960 --> 00:20:30.000
and often quite beautiful reflection of maybe

00:20:30.000 --> 00:20:32.799
his own creative anxiety and maybe echoes of

00:20:32.799 --> 00:20:35.279
that earlier it's me versus the world mentality

00:20:35.279 --> 00:20:38.299
searching for meaning and connection in a confusing

00:20:38.299 --> 00:20:41.259
world it was definitely a clear if maybe niche

00:20:41.259 --> 00:20:43.799
artistic statement but the real current success

00:20:43.799 --> 00:20:45.700
yeah the one that's getting the massive industry

00:20:45.700 --> 00:20:48.019
recognition right now is shrinking premiered

00:20:48.019 --> 00:20:51.500
2023 on apple tv plus Yeah, shrinking feels like

00:20:51.500 --> 00:20:54.380
the perfect vehicle for this current stage of

00:20:54.380 --> 00:20:57.119
his evolution. He co -created the series alongside

00:20:57.119 --> 00:21:00.259
actual comedy legends, Bill Lawrence. Scrubs,

00:21:00.339 --> 00:21:02.539
Ted Lasso creator. Right, and Brett Goldstein.

00:21:02.759 --> 00:21:05.279
Roy Kent himself from Ted Lasso. Exactly, and

00:21:05.279 --> 00:21:07.500
Siegel stars as the grieving therapist Jimmy

00:21:07.500 --> 00:21:09.940
Laird, whose kind of unconventional methods start

00:21:09.940 --> 00:21:11.880
shaking up his practice. That creative trio is

00:21:11.880 --> 00:21:13.720
fascinating. Lawrence is known for combining

00:21:13.720 --> 00:21:17.039
sentimentality with that breakneck comedic pacing.

00:21:17.539 --> 00:21:21.430
Goldstein brings that. sharp, slightly brutal,

00:21:21.630 --> 00:21:25.210
comedic edge. And Siegel provides the emotional

00:21:25.210 --> 00:21:28.250
core, the grounding vulnerability. How do those

00:21:28.250 --> 00:21:30.309
voices merge together? Well, the show really

00:21:30.309 --> 00:21:32.450
seems to thrive on that merger. Siegel's character,

00:21:32.650 --> 00:21:34.609
Jimmy, he's almost like Marshall Erickson, grown

00:21:34.609 --> 00:21:36.910
up and broken, you know? Yeah, I can see that.

00:21:37.029 --> 00:21:39.730
He has the sensitivity, but the constant optimism

00:21:39.730 --> 00:21:43.549
has been shattered by grief. And the show tackles

00:21:43.549 --> 00:21:46.990
these really modern themes. Toxic masculinity,

00:21:47.529 --> 00:21:50.589
emotional shutdown, the stigma around therapy,

00:21:50.710 --> 00:21:53.809
the messy road to vulnerability. Lawrence and

00:21:53.809 --> 00:21:56.190
Goldstein's structures kind of provide the necessary

00:21:56.190 --> 00:21:58.470
comedic guardrails, I think, allowing Siegel

00:21:58.470 --> 00:22:01.329
to explore really profound emotional territory

00:22:01.329 --> 00:22:03.930
without sacrificing the humor. And that synthesized

00:22:03.930 --> 00:22:05.710
effort has resulted in some pretty significant

00:22:05.710 --> 00:22:07.470
professional praise, hasn't it? Oh, absolutely.

00:22:07.750 --> 00:22:09.509
His work on Shrinking has earned him the kind

00:22:09.509 --> 00:22:12.809
of top -tier recognition actors dream of. Nominations

00:22:12.809 --> 00:22:15.549
for three Primetime Emmy Awards. Wow. And a Golden

00:22:15.549 --> 00:22:17.910
Globe Award nomination for Best Actor in a TV

00:22:17.910 --> 00:22:21.250
Musical or Comedy in 2024. And the entire ensemble

00:22:21.250 --> 00:22:24.130
cast also got... a Screen Actors Guild Award

00:22:24.130 --> 00:22:27.289
nomination. This is really the ultimate payoff

00:22:27.289 --> 00:22:31.289
for that big 2015 dramatic pivot and his consistent

00:22:31.289 --> 00:22:34.450
use of personal writing as the catalyst for change.

00:22:34.750 --> 00:22:36.890
Okay, so beyond the acting and the show running,

00:22:37.049 --> 00:22:39.349
and this really speaks directly to his identity

00:22:39.349 --> 00:22:42.569
as a creator, there's this whole other parallel

00:22:42.569 --> 00:22:45.269
universe of creative output that, let's be honest,

00:22:45.410 --> 00:22:48.480
very few major movie stars engage in. Right.

00:22:48.640 --> 00:22:50.859
The world of literature. Yeah. The commitment

00:22:50.859 --> 00:22:53.839
to the young adult author pivot is honestly astonishing.

00:22:54.259 --> 00:22:57.319
He announced this initiative way back in 2013,

00:22:57.599 --> 00:22:59.859
indicating he had actually been working on the

00:22:59.859 --> 00:23:02.000
concept since he was a young man. Like he conceived

00:23:02.000 --> 00:23:03.940
the story when he was only 21. That's incredible.

00:23:04.059 --> 00:23:05.960
And this isn't just like dipping a toe in the

00:23:05.960 --> 00:23:08.859
water with one book. This is a massive multi

00:23:08.859 --> 00:23:11.299
-book commitment. Totally. He started the Nightmares

00:23:11.299 --> 00:23:13.740
series, co -written with Kirsten Miller. The

00:23:13.740 --> 00:23:16.079
first novel came out in 2014 and a follow -up

00:23:16.079 --> 00:23:18.109
came out just the next year, 2015. And what's

00:23:18.109 --> 00:23:19.890
the Nightmare series about? Does it connect to

00:23:19.890 --> 00:23:22.069
his other work thematically? Well, we need to

00:23:22.069 --> 00:23:23.750
look at the content, yeah, to understand why

00:23:23.750 --> 00:23:26.630
he commits to this format. The Nightmare series

00:23:26.630 --> 00:23:30.089
explores the world of this young boy whose frightening

00:23:30.089 --> 00:23:33.349
dreams start manifesting as actual physical entities.

00:23:34.250 --> 00:23:36.569
Ooh, interesting. So it's really a book about

00:23:36.569 --> 00:23:40.930
facing and overcoming fear, but using kind of

00:23:40.930 --> 00:23:44.849
whimsy and fantasy to externalize those internal

00:23:44.849 --> 00:23:47.109
anxieties. Okay, I see the connection. Making

00:23:47.109 --> 00:23:49.670
the internal external. Exactly. It aligns perfectly

00:23:49.670 --> 00:23:52.289
with his decision to, like, stage his emotional

00:23:52.289 --> 00:23:55.230
trauma in forgetting Sarah Marshall. Same impulse,

00:23:55.390 --> 00:23:57.490
different medium. And he didn't stop there right

00:23:57.490 --> 00:23:59.990
after Nightmares. Following the success of that

00:23:59.990 --> 00:24:02.430
duology, he and Kirsten Miller launched an entirely

00:24:02.430 --> 00:24:05.710
new series, the Otherworld series. Wow. This

00:24:05.710 --> 00:24:07.990
one's even more ambitious, maybe. The first book

00:24:07.990 --> 00:24:10.289
came out in 2017, followed by Other Earth in

00:24:10.289 --> 00:24:13.809
2018 and Other Life in 2019. What's this he's

00:24:13.809 --> 00:24:16.109
tackled? These books delve into virtual reality,

00:24:16.529 --> 00:24:18.710
digital consciousness, the ethical dilemmas in

00:24:18.710 --> 00:24:21.430
gaming and AI technology. So pretty complex stuff

00:24:21.430 --> 00:24:23.950
for YA. That is. That's seven major published

00:24:23.950 --> 00:24:27.670
novels in collaboration. Seven. This commitment

00:24:27.670 --> 00:24:30.289
just proves that his creative impulse isn't limited

00:24:30.289 --> 00:24:33.589
to a writer's room or a movie set. He seems to

00:24:33.589 --> 00:24:35.930
see himself as a world builder, really, regardless

00:24:35.930 --> 00:24:38.789
of the medium. That really is proof that his

00:24:38.789 --> 00:24:42.029
desire for creative expression just transcends

00:24:42.029 --> 00:24:45.509
format, whether it's writing a little song for

00:24:45.509 --> 00:24:48.470
a stoner character on TV or mapping out a complex

00:24:48.470 --> 00:24:51.250
science fiction trilogy for young adults. The

00:24:51.250 --> 00:24:54.190
need to construct these narrative worlds seems

00:24:54.190 --> 00:24:57.220
paramount for him. Definitely. And moving to

00:24:57.220 --> 00:24:58.960
his personal life, we also find these really

00:24:58.960 --> 00:25:00.880
delightful facets of his personality that kind

00:25:00.880 --> 00:25:03.680
of defy the typical celebrity narrative. Like

00:25:03.680 --> 00:25:06.079
what? Perhaps the most charming is his surprising

00:25:06.079 --> 00:25:09.500
spiritual side. Oh, right. He is an ordained

00:25:09.500 --> 00:25:11.559
minister with the Universal Life Church. Which

00:25:11.559 --> 00:25:13.839
is great in itself, but it also allowed for this

00:25:13.839 --> 00:25:16.380
wonderfully quirky public service moment. The

00:25:16.380 --> 00:25:18.700
wedding. He actually performed a wedding ceremony

00:25:18.700 --> 00:25:21.900
live on The Tonight Show back in July 2010. How

00:25:21.900 --> 00:25:24.440
did that even happen? While the couple who enlisted

00:25:24.440 --> 00:25:27.059
his services hadn't just like reached out casually

00:25:27.059 --> 00:25:29.859
through agents, they had specifically solicited

00:25:29.859 --> 00:25:32.359
his help by putting pictures of him up all around

00:25:32.359 --> 00:25:34.839
his hometown and apparently at the bar he often

00:25:34.839 --> 00:25:38.380
frequented. That is amazing. That anecdote just

00:25:38.380 --> 00:25:40.640
captures his appeal perfectly, doesn't it? He

00:25:40.640 --> 00:25:43.640
seems accessible, charmingly goofy, and willing

00:25:43.640 --> 00:25:46.400
to participate in the real -life joy of his fans.

00:25:46.619 --> 00:25:48.920
Totally. And if we look quickly at the timeline

00:25:48.920 --> 00:25:51.119
of his notable relationships, they often seem

00:25:51.119 --> 00:25:53.460
to align with his professional phases, kind of

00:25:53.460 --> 00:25:55.299
reflecting his changing status in the public

00:25:55.299 --> 00:25:58.019
eye. Okay, like who? Well, he dated his Freaks

00:25:58.019 --> 00:26:00.720
and Geeks co -star Linda Cardellini, right? That

00:26:00.720 --> 00:26:02.779
relationship started during that early Apatow

00:26:02.779 --> 00:26:06.220
era. Then he dated actress Michelle Williams

00:26:06.220 --> 00:26:09.230
from... 2012 to 2013, which was right as he was

00:26:09.230 --> 00:26:11.710
making that big push into more serious film roles.

00:26:11.890 --> 00:26:14.549
Okay. And then he maintained a significant, really

00:26:14.549 --> 00:26:16.730
long -term relationship with photographer Alexis

00:26:16.730 --> 00:26:19.609
Mixter for nearly eight years. Eight years, wow.

00:26:19.809 --> 00:26:22.730
Yeah, between 2013 and 2021, which covers that

00:26:22.730 --> 00:26:24.970
whole period of his dramatic pivot and establishing

00:26:24.970 --> 00:26:27.529
himself as a writer and creator. And what about

00:26:27.529 --> 00:26:30.369
more recently? Well, as of the most recent source

00:26:30.369 --> 00:26:32.430
material updates we have, he seems to be in a

00:26:32.430 --> 00:26:36.250
new, exciting phase. Since 2023, he's been dating

00:26:36.250 --> 00:26:39.150
Kayla Radomski, who used to be a backup dancer

00:26:39.150 --> 00:26:41.069
for Taylor Swift. Oh, interesting connection.

00:26:41.309 --> 00:26:43.650
Yeah. And their engagement was actually announced

00:26:43.650 --> 00:26:47.450
via Instagram in June 2025. So it shows his personal

00:26:47.450 --> 00:26:49.829
life continues to kind of settle into these long,

00:26:49.890 --> 00:26:53.329
meaningful phases, evolving right alongside his

00:26:53.329 --> 00:26:55.349
professional identity. Okay, let's try and pull

00:26:55.349 --> 00:26:57.490
it all together now by just reviewing the awards

00:26:57.490 --> 00:27:00.650
that really summarize this bizarrely eclectic

00:27:00.650 --> 00:27:03.940
career. The awards really are the ultimate testament

00:27:03.940 --> 00:27:06.660
to his diversity, aren't they? You see the serious,

00:27:06.660 --> 00:27:09.559
dramatic recognition, that Independent Spirit

00:27:09.559 --> 00:27:12.359
Award nomination for Best Male Lead for playing

00:27:12.359 --> 00:27:14.420
David Foster Wallace in the end of the tour.

00:27:14.559 --> 00:27:17.220
Right. The serious cred. Then the recognition

00:27:17.220 --> 00:27:19.759
of his current creative leadership. the Golden

00:27:19.759 --> 00:27:22.819
Globe, and Emmy nominations for shrinking. Huge

00:27:22.819 --> 00:27:25.900
TV awards. Top tier stuff. But right there, sitting

00:27:25.900 --> 00:27:27.920
right next to all that serious acclaim, is the

00:27:27.920 --> 00:27:30.319
Critics' Choice Award win for Best Song for The

00:27:30.319 --> 00:27:32.960
Muppets. It's incredible. Seriously, who else

00:27:32.960 --> 00:27:36.119
has multiple Emmy nominations sitting next to

00:27:36.119 --> 00:27:38.900
an award for composing a heartfelt Muppet ballad?

00:27:39.000 --> 00:27:41.299
I can't think of many. Comedy, drama, musical

00:27:41.299 --> 00:27:43.980
composition, all recognized at the highest levels.

00:27:44.099 --> 00:27:47.240
It's wild. And just as a final note that kind

00:27:47.240 --> 00:27:49.460
of encapsulates his charming... celebrated persona.

00:27:49.940 --> 00:27:52.519
We have to mention he was named the hasty pudding

00:27:52.519 --> 00:27:55.359
man of the year back in 2012. Ah, the hasty pudding

00:27:55.359 --> 00:27:57.779
award. That's a fun one. Yeah. A prestigious

00:27:57.779 --> 00:28:00.359
honor recognizing his, you know, lasting and

00:28:00.359 --> 00:28:02.259
impressive contribution to entertainment. But

00:28:02.259 --> 00:28:07.000
with that fun, quirky Harvard edge, hashtag hashed

00:28:07.000 --> 00:28:10.000
outro. So what does this really remarkable career

00:28:10.000 --> 00:28:13.539
path ultimately teach us? about creativity, about

00:28:13.539 --> 00:28:16.559
career longevity. Jason Segel's journey, I think,

00:28:16.559 --> 00:28:18.759
is a definitive guide on how to redefine yourself

00:28:18.759 --> 00:28:21.579
in what can be a very rigid industry. He just

00:28:21.579 --> 00:28:24.359
leveraged intense personal experience, heartbreak,

00:28:24.400 --> 00:28:26.200
the naked vulnerability, their complex religious

00:28:26.200 --> 00:28:28.759
identity, his sincere love for puppets, all of

00:28:28.759 --> 00:28:32.039
it, to fuel these wildly diverse and, frankly,

00:28:32.119 --> 00:28:34.839
surprisingly successful creative outputs. The

00:28:34.839 --> 00:28:37.500
central takeaway for you, the listener, seems

00:28:37.500 --> 00:28:40.900
pretty clear. Segel just refused to be boxed

00:28:40.900 --> 00:28:45.170
in. And he achieved that refusal by consistently

00:28:45.170 --> 00:28:47.869
seizing control of the narrative. Literally.

00:28:48.569 --> 00:28:51.029
He realized, I think, that the industry would

00:28:51.029 --> 00:28:53.670
only see him as Marshall Erickson if he let them.

00:28:53.789 --> 00:28:55.690
He didn't just wait for the great roles to come

00:28:55.690 --> 00:28:59.000
along. He wrote them. Exactly. The writing. Starting

00:28:59.000 --> 00:29:02.420
way back with that awkward early song he composed

00:29:02.420 --> 00:29:05.019
for Freaks and Geeks. Yeah, that little song.

00:29:05.200 --> 00:29:07.440
Through the incredibly vulnerable script for

00:29:07.440 --> 00:29:10.579
forgetting Sarah Marshall and culminating now

00:29:10.579 --> 00:29:13.900
in his seven published novels. That was the consistent

00:29:13.900 --> 00:29:16.240
engine for change in his career. It allowed him

00:29:16.240 --> 00:29:18.660
to shift from being just a comedic actor working

00:29:18.660 --> 00:29:21.460
within that apatosphere to an acclaimed dramatic

00:29:21.460 --> 00:29:24.539
lead. And now, yeah, a successful Emmy nominated

00:29:24.539 --> 00:29:27.339
creator and showrunner in his own right. It's

00:29:27.339 --> 00:29:28.940
a really powerful. Powerful lesson in career

00:29:28.940 --> 00:29:31.420
bravery, I think. You know, when your comedic

00:29:31.420 --> 00:29:33.440
comfort zone started giving you Razzie nominations.

00:29:33.740 --> 00:29:36.339
Right. Oops. He engineered this hard left turn

00:29:36.339 --> 00:29:38.759
into probably the most intellectually challenging

00:29:38.759 --> 00:29:41.700
role he could find. And boom, it paid off immediately.

00:29:41.900 --> 00:29:45.420
It really did. So the question now, as he enters

00:29:45.420 --> 00:29:47.759
this new phase of creative control and production,

00:29:47.980 --> 00:29:51.039
is where that boundless creative energy is going

00:29:51.039 --> 00:29:54.140
to land next. Considering his deep, sustained

00:29:54.140 --> 00:29:57.720
involvement in young adult fiction. I mean, a

00:29:57.720 --> 00:30:00.240
seven book partnership is serious. Very serious.

00:30:00.279 --> 00:30:02.240
Here's a final provocative thought for you to

00:30:02.240 --> 00:30:04.900
consider. Will his next major breakthrough be

00:30:04.900 --> 00:30:07.640
purely behind the camera? Could he potentially

00:30:07.640 --> 00:30:12.500
translate his successful literary universe? You

00:30:12.500 --> 00:30:15.160
know, those complex worlds dealing with nightmares

00:30:15.160 --> 00:30:18.720
and virtual reality into a new complex cinematic

00:30:18.720 --> 00:30:20.900
universe. It's definitely possible. That transition

00:30:20.900 --> 00:30:23.500
from author to showrunner is increasingly common

00:30:23.500 --> 00:30:25.759
these days. He's got the stories already written.

00:30:25.799 --> 00:30:27.380
He's got the collaborators. He certainly has

00:30:27.380 --> 00:30:30.279
a track record now. The pages might just be the

00:30:30.279 --> 00:30:33.279
next frontier for him on screen. Fascinating

00:30:33.279 --> 00:30:35.039
thought. Thanks for diving deep with us today.

00:30:35.200 --> 00:30:36.480
My pleasure. We'll catch you next time.
