WEBVTT

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Welcome back to The Deep Dive. Today, we are

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focusing our lens on a figure who represents

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perhaps the single most confusing data set in

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modern Hollywood history. That's a good way to

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put it. A confusing data set. You know him. You

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almost certainly have an impression of him. He's

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the guy, you know, yelling at the golf ball.

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Right. Go to your home. He is the guy walking

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out of a five -star hotel in basketball shorts

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that look like they were sized for, I don't know,

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a giant? Is a very specific. very loud aesthetic

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it is we are talking about adam sandler but here's

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the mission for this deep dive we're not just

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going to quote lines from billy madison although

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we probably will we probably will but we're here

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to unpack a genuine paradox we're looking at

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a man who has generated over two billion dollars

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in global box office revenue yet simultaneously

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holds the record for some of the most uh It's

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a fascinating disconnect. I mean, if you look

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at the raw data, and we have a massive stack

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of sources here, everything from box office receipts

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to decades of film criticism and financial disclosures,

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you see two completely different stories. Two

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completely separate careers, almost. Exactly.

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In one story, he's a hack, a symbol of the death

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of cinema, you know. But in the other story,

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he is a savvy business mogul. maybe most surprisingly,

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a critical darling of the high art crowd. That's

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the part that always trips me up, the duality.

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On one hand, you have the Golden Raspberry Awards,

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the Razzies. Oh, yeah. They literally have a

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category that feels like it was invented just

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for him. He's been nominated for worst actor

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nearly a dozen times. He actually set a record

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in 2012 with Jack and Jill, winning worst actor

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and worst actress in the same year. Which is

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objectively hilarious. I mean, that's a kind

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of achievement in itself. It really is. But then

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you fast forward to 2023. He's standing at the

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Kennedy Center receiving the Mark Twain Prize

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for American humor. The highest honor. I mean,

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that's the Nobel Prize of comedy. He is standing

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where Richard Pryor stood, where George Carlin

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stood. How does that happen? And that is the

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hook of this entire deep dive. How does one man

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straddle that canyon? How can you be the antithesis

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of Judd Apatow, as one critic called him, implying

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he's anti -art? Wow. And yet be the muse for

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Paul Thomas Anderson, one of the greatest living

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filmmakers. Who is like the definition of high

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art cinema. Totally. Anderson has gone on record

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saying he has an obsession level love for Sandler's

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work. It feels impossible. It's like finding

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out that a three star Michelin chef's favorite

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meal is a gas station hot dog. Right. But maybe

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that's on us. Maybe we've been looking at Sandler

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wrong this whole time. That is exactly my read

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on the sources. We tend to view Sandler as this

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lucky glass clown who just, you know, stumbled

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into a fortune. Yeah, that he was just goofing

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around and fell backwards into half a billion

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dollars. But when you dig into the biography

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and the business moves, you find a highly trained,

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incredibly calculated operator. Okay, let's start

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with that training. Because the origin story

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isn't just funny kid from Brooklyn. No, it's

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much more academic than people realize. Adam

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Sandler was born in Brooklyn in 1966, but his

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family moved to Manchester, New Hampshire when

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he was six. So he's got those deep New England

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suburban roots. For sure. His father, Stanley,

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was an electrical engineer. His mother, Judy,

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was a nursery school teacher. Very standard,

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supportive upbringing from what all the biographical

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data says. But the spark, the comedy thing, that

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came pretty early. It did. At age 17, his brother

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urged him to get on stage at a comedy club in

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Boston. Just pushed him up there. Pretty much.

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And he found he liked it. That he had a knack

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for it. But the pivotal moment comes when he

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decides to pursue it professionally. He didn't

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just hit the open mics and hope for the best.

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Right. This is where it gets serious. No, he

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went to school. And not just any school. He applied

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to and was accepted into the Tisch School of

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the Arts at New York University. We need to pause

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and underscore that. Because that is, that's

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not what you'd expect. Tisch is serious business.

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It is the Ivy League of acting. It is method

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acting. It's Stanislavski. It's Chekhov. I mean,

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when you go to Tisch, you are learning how to

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strip yourself down emotionally, how to use your

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physical instrument to convey truth. It's not

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a joke factory. And he graduated. Right. He has

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a degree. Graduated in 1988 with a Bachelor of

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Fine Arts. OK, let me get this straight. When

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we see him in Billy Madison making gibberish

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noises or doing that weird baby voice. Yeah.

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That isn't just a guy goofing off. That is a

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choice made by a technically trained BFA -holding

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actor. Exactly. It recontextualizes everything.

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It means he understands the rules of performance

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well enough to break them for comedic effect.

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It's not an accident. It's a deliberate choice.

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Yeah. And he was working hard right out of the

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gate. While he was at NYU, he landed a recurring

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role as Smitty on The Cosby Show. Smitty. I remember

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him. He was Theo Huxtable's friend. Right. And

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he played it straight. He was learning the rhythm

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of a multi -camera sitcom. He was on the set

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of the biggest show in the world, just absorbing

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it all. He was also on that MTV game show, right?

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Remote Control. The stud boy, yeah. Yeah. He

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was getting his reps in, doing anything and everything.

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But the big break, the moment that actually changed

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the trajectory of American comedy, happened in

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a comedy club in Los Angeles. This is the Dennis

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Miller connection. Tell us about that. Okay,

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so Dennis Miller was the anchor of Weekend Update

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on Saturday Night Live at the time. A huge deal.

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He just happened to catch Sandler's stand -up

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set. And what was Sandler's act like back then?

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Well, you have to remember, late 80s comedy was

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very observational. It was Jerry Seinfeld. It

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was what's the deal with airline food? Right.

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The set up punchline structure. Sandler wasn't

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doing that at all. He was doing the guitar. He

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was doing characters. He was manic. He was musical.

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He was weird. It was a totally different energy.

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So Miller sees this raw talent. He sees this

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raw energy. and immediately called Lorne Michaels.

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And the sources say he didn't just say, hey,

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check this kid out. He vouched for him. He put

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his own reputation on the line. And getting a

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recommendation from the Weekend Update anchor

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to the creator of the show, that's the golden

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ticket. It gets you in the room. Sandler was

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hired as a writer in 1990. A writer, not a performer.

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Not initially. He had to earn his way onto the

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screen by writing sketches that made people laugh

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in the read -through. He had to prove his value

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in the writer's room first. And that era of SNL,

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the early 90s, it's legendary now. The bad boys

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of SNL. It was a very specific cultural moment.

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You had Sandler, Chris Farley, David Spade, Chris

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Rock, Rob Schneider. They created a vibe that

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was less about... polished political satire and

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more about the chaotic energy of a college dorm

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room. And it really connected with a younger

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audience. Absolutely. But Sandler's specific

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contribution wasn't really sketches, was it?

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He found his own lane. It was the update desk.

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That was his stroke of genius. He realized he

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wasn't going to beat Phil Hartman at impressions.

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He wasn't going to beat Mike Myers at complex

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character work. So he brought his stand -up act

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to the desk. He brought the guitar. And the songs,

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the Thanksgiving song, the Chinooka song. The

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Chinooka song is honestly a masterpiece of efficiency.

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It really is. I mean, think about it. Before

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that song, Jewish kids in December had zero representation

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in popular culture. It was all Christmas carols

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all the time. None. And Sandler comes on national

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television and just starts listing famous Jews

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in a simple, funny rhyme scheme. Paul Newman's

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half Jewish. Goldie Hawn is, too. It was identity

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politics wrapped in a nursery rhyme. It was so

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simple and brilliant. It made him a star because

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it felt personal and authentic. But despite the

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popularity, and they were very popular. Oh, massively.

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The suits at NBC weren't laughing. No. This is

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where the business reality clashes with the creative.

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The ratings for the show were fluctuating, the

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budget was high, but more importantly, the executives

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felt the show had become... Unprofessional. Unprofessional.

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They thought the bad boys were too lowbrow. They

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didn't get the humor. There was this perception

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that they were just goofing off and breaking

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character all the time. Which, to be fair, they

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were. They were, but that was part of the charm.

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The audience loved it. The execs didn't. So in

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1995, we get the incident that defines his career.

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The firing. The purge. NBC fired Adam Sandler

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and Chris Farley. It is still mind -blowing to

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me. You fire your two biggest breakout stars.

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In hindsight, it looks like financial suicide

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for the network. It does now. But at the time,

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they wanted a clean slate. They wanted to professionalize

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the show again. And Sandler has talked about

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this moment, right? He didn't quit. Oh, no. He's

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been very clear about this, especially in interviews

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with Conan O 'Brien. He didn't walk out in protest.

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His agent called him and said. They don't want

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you back. Imagine the psychology of that. Yeah.

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You were in your mid -20s, you were one of the

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most famous comedians in the country, and you

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just got kicked out of the clubhouse. That has

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to create a massive chip on your shoulder. A

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boulder. And that chip became his fuel. He later

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said that getting fired was the best thing that

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could have happened to him because it removed

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the safety net. He couldn't just stay on TV forever.

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He had to become a movie star. And he had to

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do it his way to prove them wrong. He had to

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prove them wrong. And you see that drive in what

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happens next. When he finally returned to host

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SNL in 2019, he did a whole song about it in

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his monologue. Oh, I remember that. I was fired.

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I was fired. He completely owned it. And then

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at the end, he did this incredibly moving tribute

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to Chris Farley. You can see how much that whole

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experience shaped him. And boy, did he prove

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them wrong. This kicks off the golden era. From

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1995 to 1998, the output is just staggering.

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It's an incredible run. Billy Madison comes out

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in 95, almost immediately after he gets fired.

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Then Happy Gilmore in 96. The Wedding Singer

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in 98. The Waterboy also in 98. It's just hit

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after hit after hit. And these are the films

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that defined a generation. And they established

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the Sandler archetype that we need to unpack.

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The Man Child. Yes. But it's specific, right?

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It's not just an immature guy. No, it's very

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specific. In Billy Madison, he is literally repeating

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grade school. In The Waterboy, he lives with

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his mama and talks like a toddler. In Happy Gilmore,

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he acts like a petulant teenager who can't control

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his temper. But the key ingredient isn't just

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the immaturity. It's the rage. The screaming,

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yes. The repressed rage. The comedy in these

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films almost always comes from the tension between

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his sweet, innocent, almost childlike demeanor.

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And these sudden, violent, volcanic explosions

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of anger. It's cathartic. Why did that resonate

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so much in the late 90s? What was going on in

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the culture? I think it tapped into a very specific

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male anxiety of that era. You had a generation

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of guys, you know, Gen X guys, who felt... A

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bit stunted, a bit awkward, maybe a bit angry

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at the world for reasons they couldn't articulate.

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And Sandler gave that feeling a voice, a very

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loud, screaming voice. He made it funny. He made

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the loser the hero who could, you know, beat

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up the smarmy villain. Or Bob Barker. Or Bob

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Barker. And financially, it worked beyond anyone's

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wildest dreams. The Waterboy is the key statistic

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here again. Yeah, that one really changed the

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game. The Waterboy changed everything. It was

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released in 1998. It was a weird movie, a football

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comedy. where he talks with a lisp and tackles

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people with high -quality H2O. Critics absolutely

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despised it. I remember the reviews. They were

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brutal. Just shredded him. But it opened to massive

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numbers. It grossed nearly $190 million globally

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on a $23 million budget. That is Marvel -level

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profit margins. It made him a truly bankable

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star. It meant that he could open a movie on

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his name alone, regardless of the premise, regardless

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of the reviews. The audience had chosen. The

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audience had chosen. In fact, he actually had

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to drop out of a dark comedy called Very Bad

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Things because the Waterboy got so big he needed

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to manage the fallout and the fame. He was officially

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A -list. So he has the leverage, he has the money,

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and this is where he builds the empire. Happy

00:12:05.879 --> 00:12:09.139
Madison Productions. Founded in 1999. Named after

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the two movies that started it all. Happy Gilmore

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and Billy Madison. A great logo, too. That picture

00:12:14.100 --> 00:12:16.559
of his dad. It is. And he set up on the Sony

00:12:16.559 --> 00:12:19.519
Columbia lot in Culver City. And this is where

00:12:19.519 --> 00:12:22.000
the controversy, or at least the critical backlash,

00:12:22.259 --> 00:12:25.299
usually starts. The nepotism argument. The idea

00:12:25.299 --> 00:12:27.299
that Happy Madison is just a scheme to pay his

00:12:27.299 --> 00:12:29.419
friends to go on vacation. And if you look at

00:12:29.419 --> 00:12:31.679
the filmography grown -ups, just go with it.

00:12:31.740 --> 00:12:34.059
Blended. They're often set in resorts. Hawaii,

00:12:34.360 --> 00:12:37.889
Africa, Italy. You're not wrong. And he casts

00:12:37.889 --> 00:12:41.049
David Spade, Rob Schneider, Kevin James, Chris

00:12:41.049 --> 00:12:43.909
Rock, the same crew. Critics look at this and

00:12:43.909 --> 00:12:46.389
say, this is lazy. This is a scam. These are

00:12:46.389 --> 00:12:50.370
just whole movies. But is it? Or is it genius?

00:12:51.330 --> 00:12:53.470
Well, from a labor and business perspective,

00:12:53.710 --> 00:12:56.450
it is brilliant. Explain that. In Hollywood,

00:12:56.570 --> 00:12:59.049
most people are gig workers. You finish a movie,

00:12:59.190 --> 00:13:01.289
you are unemployed. You're always looking for

00:13:01.289 --> 00:13:04.490
the next job. Sandler created a... A repertory

00:13:04.490 --> 00:13:07.789
company. A stable. A stable. If you are a writer,

00:13:07.909 --> 00:13:10.549
a camera operator, a set designer, or an actor

00:13:10.549 --> 00:13:13.149
in a circle, you have job security. You have

00:13:13.149 --> 00:13:15.250
a pension. You have steady work. It's like he

00:13:15.250 --> 00:13:18.029
created a union for his friends. Exactly. And

00:13:18.029 --> 00:13:20.210
that breeds immense loyalty. He keeps the same

00:13:20.210 --> 00:13:22.690
crew for decades. That means productions are

00:13:22.690 --> 00:13:24.830
incredibly efficient because everyone knows the

00:13:24.830 --> 00:13:27.350
shorthand. There is no ego on set because everyone

00:13:27.350 --> 00:13:30.139
is part of the tribe. So he prioritized loyalty

00:13:30.139 --> 00:13:32.600
over critical acclaim. He prioritized autonomy

00:13:32.600 --> 00:13:35.019
by keeping it in the family. He didn't have to

00:13:35.019 --> 00:13:37.139
listen to studio notes. He didn't have to audition

00:13:37.139 --> 00:13:39.220
new people. He could make the movies he wanted

00:13:39.220 --> 00:13:41.080
to make with the people he wanted to make them

00:13:41.080 --> 00:13:43.500
with. And get paid a fortune to do it. Yeah,

00:13:43.500 --> 00:13:46.019
and get paid a fortune. But just as we had him

00:13:46.019 --> 00:13:48.639
boxed in as the lazy comedy guy, the guy making

00:13:48.639 --> 00:13:52.179
vacation movies, he does the thing that breaks

00:13:52.179 --> 00:13:55.960
the model, the pivot. 2002, Punch Drunk Love.

00:13:56.379 --> 00:13:59.039
This is the moment where the Tisch graduate reemerges

00:13:59.039 --> 00:14:01.460
from the swamp of fart jokes. It's the glitch

00:14:01.460 --> 00:14:05.399
in the matrix. Paul Thomas Anderson, who had

00:14:05.399 --> 00:14:08.080
just made Magnolia and Boogie Nights, two of

00:14:08.080 --> 00:14:10.200
the most critically acclaimed films of the era.

00:14:10.299 --> 00:14:12.179
Yeah, he was the new Scorsese. He approaches

00:14:12.179 --> 00:14:14.700
Sandler. Now, usually serious directors avoid

00:14:14.700 --> 00:14:17.159
comic actors unless they want them to play the

00:14:17.159 --> 00:14:19.840
comic relief. Anderson wanted Sandler to be the

00:14:19.840 --> 00:14:23.080
romantic lead in a dark, strange, arthouse film.

00:14:23.279 --> 00:14:25.919
Why? What did Anderson see that other people

00:14:25.919 --> 00:14:28.860
were missing? He saw the anger. Anderson has

00:14:28.860 --> 00:14:30.980
said in interviews that he loved Big Daddy. Big

00:14:30.980 --> 00:14:33.299
Daddy. Yes. He said he would watch it over and

00:14:33.299 --> 00:14:35.820
over. He saw that beneath the jokes, there was

00:14:35.820 --> 00:14:38.360
a palpable sense of loneliness and rage in Sandler's

00:14:38.360 --> 00:14:41.179
eyes. He wrote the character of Barry Egan specifically

00:14:41.179 --> 00:14:44.039
for Sandler. Barry Egan is such a fascinating

00:14:44.039 --> 00:14:46.059
character. He wears that one blue suit the whole

00:14:46.059 --> 00:14:48.620
movie. He collects pudding cups for airline miles.

00:14:48.860 --> 00:14:52.580
And he has these terrifying, unpredictable outbursts.

00:14:53.360 --> 00:14:56.480
There is that scene where his sister is nagging

00:14:56.480 --> 00:14:58.960
him on the phone, and he just silently, efficiently

00:14:58.960 --> 00:15:01.320
shatters the sliding glass door with a hammer.

00:15:01.500 --> 00:15:04.600
It's not funny. It's scary. It's real. It's taking

00:15:04.600 --> 00:15:07.340
that man -child -with -rage persona from his

00:15:07.340 --> 00:15:09.980
comedies and stripping all the humor away, leaving

00:15:09.980 --> 00:15:12.259
only the pathology. And Sandler was terrified

00:15:12.259 --> 00:15:15.320
to take the role. He was. The story goes that

00:15:15.320 --> 00:15:18.679
he told Anderson, I can't do this. I saw Magnolia.

00:15:18.759 --> 00:15:21.600
You're too good for me. He had imposter syndrome.

00:15:21.659 --> 00:15:23.840
He was afraid he couldn't measure up. But Anderson

00:15:23.840 --> 00:15:26.899
saw something. Anderson convinced him that he

00:15:26.899 --> 00:15:29.159
didn't need to act in the traditional sense.

00:15:29.340 --> 00:15:32.019
He just needed to be a stripped down, vulnerable

00:15:32.019 --> 00:15:34.799
version of himself. He saw the potential that

00:15:34.799 --> 00:15:37.299
was always there. The result was undeniable.

00:15:37.519 --> 00:15:40.399
Even Roger Ebert, who famously hated Sandler's

00:15:40.399 --> 00:15:42.220
comedies, I think he called one of them an act

00:15:42.220 --> 00:15:44.460
of vandalism against cinema. He really did. He

00:15:44.460 --> 00:15:47.179
completely flipped. Ebert's review of Punch Drunk

00:15:47.179 --> 00:15:49.860
Love is essential reading for anyone trying to

00:15:49.860 --> 00:15:53.320
understand Sandler. He argued that the film deconstructed

00:15:53.320 --> 00:15:55.259
the Sandler persona. What did he mean by that?

00:15:55.639 --> 00:15:58.620
He said that Sandler had been wasted in bad scripts

00:15:58.620 --> 00:16:01.480
his whole career and that this film revealed

00:16:01.480 --> 00:16:03.840
that the man -child was actually a tragic figure.

00:16:04.059 --> 00:16:07.200
He called it the key to all Adam Sandler films.

00:16:07.340 --> 00:16:10.360
Wow. He saw that Barry Egan was just Billy Madison

00:16:10.360 --> 00:16:13.639
without the jokes. A love -starved, lonely man

00:16:13.639 --> 00:16:16.340
with deep -seated anger issues. It earned him

00:16:16.340 --> 00:16:18.600
a Golden Globe nomination. It proved he had the

00:16:18.600 --> 00:16:22.559
chops. But then... He didn't stay there. He didn't

00:16:22.559 --> 00:16:25.240
become a serious actor full -time. No, and that

00:16:25.240 --> 00:16:27.779
is what confuses people. He went right back to

00:16:27.779 --> 00:16:30.000
making Mr. Deeds and Click. He treated the art

00:16:30.000 --> 00:16:32.320
film like a side project, like a one -off. But

00:16:32.320 --> 00:16:34.500
he kept divvying back in. It wasn't just a fluke.

00:16:34.539 --> 00:16:38.259
Not at all. In 2007, he does Reign Over Me, where

00:16:38.259 --> 00:16:40.299
he played a man who lost his entire family in

00:16:40.299 --> 00:16:43.460
9 -11. That was a heavy, heavy role. Just pure

00:16:43.460 --> 00:16:45.909
grief. And he was incredible in it. Then the

00:16:45.909 --> 00:16:48.250
Meyerowitz stories in 2017 with Noah Baumbach.

00:16:48.370 --> 00:16:51.549
Another indie darling director. Exactly. It premiered

00:16:51.549 --> 00:16:53.830
at Cannes. Critics there were saying with no

00:16:53.830 --> 00:16:56.169
shtick to fall back on, Sandler is forced to

00:16:56.169 --> 00:16:58.809
act and it's a glorious thing to watch. And then

00:16:58.809 --> 00:17:01.509
the big one. The one that felt like a culmination

00:17:01.509 --> 00:17:04.369
of all of this. The heart attack in movie form.

00:17:04.930 --> 00:17:08.819
Uncut Gems in 2019. Oh man. Directed by the Sasty

00:17:08.819 --> 00:17:11.720
brothers, this movie is a stress test. It's two

00:17:11.720 --> 00:17:14.779
hours of pure anxiety. Sandler plays Howard Ratner,

00:17:14.920 --> 00:17:17.180
a jeweler in the Diamond District who is a gambling

00:17:17.180 --> 00:17:19.559
addict, and he is just making one bad decision

00:17:19.559 --> 00:17:22.529
after another. It is the most anxious I have

00:17:22.529 --> 00:17:24.809
ever been in a movie theater. My shoulders were

00:17:24.809 --> 00:17:27.029
up by my ears the entire time. The Safdie brothers

00:17:27.029 --> 00:17:28.970
did something brilliant. They took Sandler's

00:17:28.970 --> 00:17:31.789
natural charisma, that fast -talking, likable

00:17:31.789 --> 00:17:34.750
salesman energy, and they weaponized it. They

00:17:34.750 --> 00:17:37.549
made it frantic and desperate. You root for Howard

00:17:37.549 --> 00:17:40.109
even though he is an absolute train wreck. You

00:17:40.109 --> 00:17:42.410
can't help it. And it's widely considered his

00:17:42.410 --> 00:17:45.089
career best performance. The critical acclaim

00:17:45.089 --> 00:17:47.390
was universal. He won the Independent Spirit

00:17:47.390 --> 00:17:50.329
Award for Best Male Lead. He did, and he was

00:17:50.329 --> 00:17:53.250
famously snubbed by the Oscars, which actually

00:17:53.250 --> 00:17:55.630
created a huge wave of sympathy for him. People

00:17:55.630 --> 00:17:58.410
were outraged. It solidified his status as a

00:17:58.410 --> 00:18:01.170
great actor who chooses not to act. It gave him

00:18:01.170 --> 00:18:04.049
this artistic credibility that money can't buy.

00:18:04.250 --> 00:18:06.849
It proved that Punch Drunk Love wasn't a fluke.

00:18:07.150 --> 00:18:10.009
The talent was always there, waiting for the

00:18:10.009 --> 00:18:12.430
right director to pull it out. And speaking of

00:18:12.430 --> 00:18:14.549
money, let's pivot to the business side again,

00:18:14.670 --> 00:18:18.150
because around 2014, the industry changed and

00:18:18.150 --> 00:18:20.750
Sandler was the canary in the coal mine. This

00:18:20.750 --> 00:18:23.549
is the Netflix era. And to understand this, you

00:18:23.549 --> 00:18:26.470
have to look at the landscape in 2014. Streaming

00:18:26.470 --> 00:18:28.930
was still kind of finding its footing with original

00:18:28.930 --> 00:18:31.609
movies. The prestige was still in the movie theater.

00:18:31.690 --> 00:18:34.269
Right. If you're a big star, you wanted the red

00:18:34.269 --> 00:18:36.869
carpet premiere. You wanted the box office opening

00:18:36.869 --> 00:18:39.529
weekend numbers. That was the metric of success.

00:18:39.809 --> 00:18:42.529
But Sandler's box office was starting to soften

00:18:42.529 --> 00:18:45.769
a little bit. It was. Movies like That's My Boy

00:18:45.769 --> 00:18:48.029
and Blended weren't the massive hits his earlier

00:18:48.029 --> 00:18:50.990
films were. But Sandler looked at the other data.

00:18:51.230 --> 00:18:53.869
He saw that while his box office was softening,

00:18:53.950 --> 00:18:57.269
his DVD sales and his cable rerun numbers were

00:18:57.269 --> 00:18:59.710
astronomical. People loved watching it at home.

00:18:59.829 --> 00:19:02.390
Exactly. He realized his audience was aging.

00:19:03.130 --> 00:19:05.329
The frat guys who loved Billy Madison were now

00:19:05.329 --> 00:19:08.190
dads in their 30s and 40s. They're tired. They're

00:19:08.190 --> 00:19:10.069
tired. They didn't want to hire a babysitter

00:19:10.069 --> 00:19:12.309
and pay 20 bucks for popcorn. They wanted to

00:19:12.309 --> 00:19:14.509
sit on the couch and watch The Sandman. So he

00:19:14.509 --> 00:19:16.750
saw where the puck was going. He got there first.

00:19:17.390 --> 00:19:20.430
In 2014, he signed a four -movie deal with Netflix.

00:19:20.829 --> 00:19:24.230
A massive deal. And this was a huge gamble for

00:19:24.230 --> 00:19:26.250
Netflix at the time. It was a huge gamble. And

00:19:26.250 --> 00:19:29.049
the first movie out of the gate was The Ridiculous

00:19:29.049 --> 00:19:32.950
Six. Oh, boy. The ridiculous. A Western spoof.

00:19:33.009 --> 00:19:35.710
And we had to be honest here. Critically, it

00:19:35.710 --> 00:19:38.410
was a disaster. Disaster is putting it mildly.

00:19:38.549 --> 00:19:42.250
It has a zero percent on Rotten Tomatoes. Zero.

00:19:42.670 --> 00:19:46.450
Not one positive review. Critics called it unwatchable.

00:19:46.609 --> 00:19:48.930
They accused it of being racially insensitive.

00:19:49.509 --> 00:19:52.089
The narrative from the media was Sandler is washed

00:19:52.089 --> 00:19:54.319
up. This Netflix thing is a failure. But then

00:19:54.319 --> 00:19:56.680
the data came out. And this is the Sandler paradox

00:19:56.680 --> 00:19:58.980
in its purest form. Netflix, who are usually

00:19:58.980 --> 00:20:01.019
very secretive with their numbers, released a

00:20:01.019 --> 00:20:03.440
statement. What did it say? They said that in

00:20:03.440 --> 00:20:05.839
its first 30 days, The Ridiculous Six was viewed

00:20:05.839 --> 00:20:07.980
more times than any other movie in the history

00:20:07.980 --> 00:20:10.160
of the platform up to that point. That is mind

00:20:10.160 --> 00:20:11.819
blowing. The critics said, don't watch this.

00:20:11.960 --> 00:20:14.480
And the entire world said, hold my beer. We are

00:20:14.480 --> 00:20:16.599
watching it immediately. It proved to Netflix

00:20:16.599 --> 00:20:20.019
and to the whole industry that Sandler is completely

00:20:20.019 --> 00:20:24.019
critic proof. His fans do not read reviews. They

00:20:24.019 --> 00:20:26.579
are loyal to the brand, not to the Rotten Tomatoes

00:20:26.579 --> 00:20:28.960
score. So Netflix doubled down? Oh, they went

00:20:28.960 --> 00:20:30.880
all in. They realized they had a captive audience.

00:20:31.000 --> 00:20:33.980
They renewed the deal in 2020 for four more movies.

00:20:34.119 --> 00:20:36.319
And the money involved here is just staggering.

00:20:36.640 --> 00:20:40.259
The 2020 deal was reportedly worth up to $275

00:20:40.259 --> 00:20:45.720
million. $275 million for four movies. That is

00:20:45.720 --> 00:20:48.730
guaranteed cash. That is the key shift. In the

00:20:48.730 --> 00:20:51.109
old theatrical model, you often get paid based

00:20:51.109 --> 00:20:53.289
on how well the movie does back end points. Right.

00:20:53.410 --> 00:20:55.410
If it's a hit, you get rich. If it's a bomb,

00:20:55.529 --> 00:20:57.990
you don't. With Netflix, he gets paid up front.

00:20:58.490 --> 00:21:00.890
It completely removes the risk. It made him the

00:21:00.890 --> 00:21:03.950
highest paid actor in Hollywood in 2023, earning

00:21:03.950 --> 00:21:07.109
$73 million in a single year. So he shifted the

00:21:07.109 --> 00:21:09.529
entire industry model from high risk box office

00:21:09.529 --> 00:21:12.170
to high reward subscription retention for a streaming

00:21:12.170 --> 00:21:14.910
service. He essentially became his own studio

00:21:14.910 --> 00:21:17.690
system inside of Netflix. And he's using it to

00:21:17.690 --> 00:21:20.410
do everything. Murder Mystery with Jennifer Aniston

00:21:20.410 --> 00:21:23.349
was a massive global hit. Hubie Halloween was

00:21:23.349 --> 00:21:25.789
a huge hit. And he also used the Netflix deal

00:21:25.789 --> 00:21:28.880
to make Hustle. Exactly. A serious sports drama

00:21:28.880 --> 00:21:31.539
that got him a Screen Actors Guild Award nomination.

00:21:31.920 --> 00:21:34.299
So he gets to make his broad comedies and his

00:21:34.299 --> 00:21:37.099
prestige dramas all under the same roof with

00:21:37.099 --> 00:21:39.539
no financial risk. It's an unbelievable setup.

00:21:39.740 --> 00:21:41.700
He's having his cake and eating it, too. He bought

00:21:41.700 --> 00:21:44.220
the whole bakery. Let's talk about the man behind

00:21:44.220 --> 00:21:46.700
the brand. Because for a guy worth nearly half

00:21:46.700 --> 00:21:48.619
a billion dollars, he sure doesn't dress like

00:21:48.619 --> 00:21:51.569
it. The scumbro aesthetic. Or as some call it,

00:21:51.589 --> 00:21:54.289
the grocery run look. It is iconic at this point.

00:21:54.329 --> 00:21:58.049
The XXXL t -shirts from like a random charity

00:21:58.049 --> 00:22:00.990
5K he did in 1998. The basketball shorts that

00:22:00.990 --> 00:22:04.069
go down to his shins. The Ugg boots. The weirdly

00:22:04.069 --> 00:22:06.450
high socks. It's funny because for years the

00:22:06.450 --> 00:22:08.609
tabloids mocked him. Look at Adam Sandler. He

00:22:08.609 --> 00:22:10.910
looks like he lost his luggage. But something

00:22:10.910 --> 00:22:14.769
shifted. Something shifted. In 2021, Vogue magazine,

00:22:15.150 --> 00:22:17.829
the Bible of high fashion, named him a style

00:22:17.829 --> 00:22:20.849
icon. We have truly entered the Twilight Zone

00:22:20.849 --> 00:22:24.069
when Adam Sandler is a Vogue icon. But it makes

00:22:24.069 --> 00:22:27.150
sense in the context of Gen Z. There is this

00:22:27.150 --> 00:22:30.349
trend called normcore. It's about rejecting the

00:22:30.349 --> 00:22:33.369
polished, curated, perfect look of Instagram

00:22:33.369 --> 00:22:36.269
influencers. And Sandler is the king of uncurated.

00:22:36.369 --> 00:22:38.750
He represents comfort. He represents authenticity.

00:22:39.130 --> 00:22:42.190
His clothes say, I am so rich and so comfortable

00:22:42.190 --> 00:22:44.509
with myself that I do not need to impress you.

00:22:44.670 --> 00:22:47.710
It's a power move. It really is. He told Esquire

00:22:47.710 --> 00:22:49.569
in an interview that he was working that angle

00:22:49.569 --> 00:22:51.250
for years. He joked for a while, I was like,

00:22:51.289 --> 00:22:53.589
please accept me and the way I dress. And 30

00:22:53.589 --> 00:22:56.109
years later, they finally came around. He outlasted

00:22:56.109 --> 00:22:58.769
fashion itself. He did. There are now brands,

00:22:58.789 --> 00:23:01.369
like one called Old Jewish Men, that literally

00:23:01.369 --> 00:23:04.190
sell shorts inspired by his look. That's incredible.

00:23:04.250 --> 00:23:07.839
And it ties into his other obsession. He's a

00:23:07.839 --> 00:23:10.000
legitimate hoop head. The stories are legendary.

00:23:10.420 --> 00:23:13.140
He's on tour for stand up or filming a movie

00:23:13.140 --> 00:23:15.640
in some random town. And he just shows up at

00:23:15.640 --> 00:23:18.299
a local YMCA or a park looking for a pickup game.

00:23:18.460 --> 00:23:20.819
And he plays in the outfit. He plays in the baggy

00:23:20.819 --> 00:23:23.440
shorts and the oversized polo shirt. There are

00:23:23.440 --> 00:23:25.559
hundreds of videos online of him just draining

00:23:25.559 --> 00:23:28.880
threes in a random gym. Is he actually any good?

00:23:29.559 --> 00:23:31.519
Or do people just, you know, let him win because

00:23:31.519 --> 00:23:33.559
he's Adam Sandler? No, the scouting report is

00:23:33.559 --> 00:23:36.640
solid. He's a playmaker. He's known for creative,

00:23:36.839 --> 00:23:39.240
no -look passing. He's not going to dunk on you,

00:23:39.279 --> 00:23:41.380
but he understands the geometry of the game.

00:23:41.519 --> 00:23:44.019
He plays hard, too. Oh, yeah. He has broken his

00:23:44.019 --> 00:23:46.500
ankle. He's had shoulder surgery from basketball

00:23:46.500 --> 00:23:50.099
injuries. This is not a casual hobby. I love

00:23:50.099 --> 00:23:52.119
that image. You go to the gym to get a run in,

00:23:52.200 --> 00:23:54.480
and Adam Sandler throws you a no -look pass.

00:23:54.759 --> 00:23:58.079
It's so... Un -Hollywood. It grounds him. It

00:23:58.079 --> 00:24:00.240
keeps him connected to that regular guy persona.

00:24:00.279 --> 00:24:03.000
If he was playing polo or yachting, the brand

00:24:03.000 --> 00:24:05.660
wouldn't work. But pickup basketball? That's

00:24:05.660 --> 00:24:08.180
accessible. That's relatable. Speaking of grounding,

00:24:08.380 --> 00:24:10.940
his family seems to be the absolute center of

00:24:10.940 --> 00:24:13.400
his universe. Absolutely. He has been married

00:24:13.400 --> 00:24:16.380
to Jackie Titone since 2003. She converted to

00:24:16.380 --> 00:24:18.339
Judaism when they married. They have two daughters,

00:24:18.519 --> 00:24:20.940
Sadie and Sunny. And if you've watched his recent

00:24:20.940 --> 00:24:22.859
movies, you know them very well. They are the

00:24:22.859 --> 00:24:25.980
stars now. His recent Netflix movie, You Are

00:24:25.980 --> 00:24:28.900
So Not Invited to My Bat Mitzvah, was basically

00:24:28.900 --> 00:24:32.119
a Sandler home movie with a Netflix budget. His

00:24:32.119 --> 00:24:34.400
daughters played the leads. His wife was in it.

00:24:34.440 --> 00:24:36.839
He played the supporting dad role. And of course,

00:24:36.839 --> 00:24:39.559
the critics screamed, nepotism, baby. They did.

00:24:39.759 --> 00:24:42.940
But again, does Sandler care? His brand is loyalty.

00:24:43.220 --> 00:24:45.460
His brand is family. Why wouldn't he put his

00:24:45.460 --> 00:24:48.339
kids in the movie? It fits the ethos of Happy

00:24:48.339 --> 00:24:50.700
Madison perfectly. He's not just employing his

00:24:50.700 --> 00:24:52.440
friends anymore. He's employing his whole family.

00:24:52.880 --> 00:24:55.819
Even his nephew, Jared, gets roles. Everyone

00:24:55.819 --> 00:24:58.420
gets a part. It's the family business. One thing

00:24:58.420 --> 00:25:00.660
he keeps strictly out of the movies and really

00:25:00.660 --> 00:25:03.359
out of his public life is politics. This is a

00:25:03.359 --> 00:25:06.099
very deliberate and I think very smart choice

00:25:06.099 --> 00:25:08.319
from a business perspective. He's pretty private

00:25:08.319 --> 00:25:11.160
about it. Very. But the public records show he

00:25:11.160 --> 00:25:13.539
is a registered Republican, which is somewhat

00:25:13.539 --> 00:25:16.529
rare in the Hollywood ecosystem. He performed

00:25:16.529 --> 00:25:18.789
at the Republican National Convention in 2004

00:25:18.789 --> 00:25:22.190
and donated to Rudy Giuliani's presidential campaign

00:25:22.190 --> 00:25:24.589
in 2008. But you never hear him on a soapbox.

00:25:24.650 --> 00:25:27.230
He's not on Twitter arguing with people. Never.

00:25:27.589 --> 00:25:30.670
In an era where every celebrity feels the need

00:25:30.670 --> 00:25:33.829
to weigh in on every single issue. Sandler is

00:25:33.829 --> 00:25:36.829
a ghost. He doesn't preach. He doesn't alienate.

00:25:36.930 --> 00:25:38.910
He knows who his audience is. He knows his audience

00:25:38.910 --> 00:25:41.529
is broad. He has fans in red states and blue

00:25:41.529 --> 00:25:45.089
states. He stays in his lane. Comedy, family,

00:25:45.309 --> 00:25:48.230
sports. It protects the brand. Before we wrap

00:25:48.230 --> 00:25:50.369
up, I feel like we have to mention the audio

00:25:50.369 --> 00:25:52.690
career. Because before the movies, there were

00:25:52.690 --> 00:25:54.849
the albums. The albums were the proof of concept.

00:25:54.910 --> 00:25:57.029
They were huge. They're all going to laugh at

00:25:57.029 --> 00:25:59.390
you in 1993. And what the hell happened to me

00:25:59.390 --> 00:26:02.490
in 1996? Both went 2X platinum. I mean, they

00:26:02.490 --> 00:26:04.230
were selling millions of copies. I wore those

00:26:04.230 --> 00:26:07.170
tapes out. The Goat, Tollbooth Willie, The Longest

00:26:07.170 --> 00:26:09.630
Pee. They were a mix of sketches and his songs.

00:26:09.849 --> 00:26:11.730
And they showed that his comedy could sustain

00:26:11.730 --> 00:26:14.299
a long format. It wasn't just a four -minute

00:26:14.299 --> 00:26:16.839
bit on Weekend Update. He could build a world

00:26:16.839 --> 00:26:19.000
with sound and characters that you could listen

00:26:19.000 --> 00:26:21.480
to for an hour. Without the success of those

00:26:21.480 --> 00:26:23.680
albums, I'm not sure he gets the green light

00:26:23.680 --> 00:26:25.940
for Billy Madison. I think you're right. They

00:26:25.940 --> 00:26:27.720
laid the groundwork for everything that came

00:26:27.720 --> 00:26:30.599
after. So let's bring it all home. We've looked

00:26:30.599 --> 00:26:33.880
at the Tisch training, the SNL firing, the box

00:26:33.880 --> 00:26:36.059
office records, the arthouse acclaim, and the

00:26:36.059 --> 00:26:39.480
Netflix empire. What is the legacy of Adam Sandler?

00:26:40.009 --> 00:26:42.869
I think the Mark Twain Prize in 2023 was the

00:26:42.869 --> 00:26:45.730
capstone. It was the establishment finally admitting

00:26:45.730 --> 00:26:48.089
defeat. Admitting defeat. Yeah. Admitting, OK,

00:26:48.230 --> 00:26:50.950
you won. For decades, the critical establishment

00:26:50.950 --> 00:26:54.509
dismissed him, mocked him, but he outlasted them.

00:26:54.630 --> 00:26:58.069
He built something so big and so successful that

00:26:58.069 --> 00:27:00.369
they had no choice but to acknowledge his impact

00:27:00.369 --> 00:27:03.450
on American humor. He beat the system by creating

00:27:03.450 --> 00:27:05.940
his own system. He hacked it. Most people in

00:27:05.940 --> 00:27:07.759
Hollywood have to compromise. They do movies,

00:27:07.819 --> 00:27:09.819
they hate to pay the bills, or they beg for funding

00:27:09.819 --> 00:27:12.240
for their passion projects. Saylor constructed

00:27:12.240 --> 00:27:14.460
a reality where he does exactly what he wants

00:27:14.460 --> 00:27:17.480
all the time. He split his career into two distinct

00:27:17.480 --> 00:27:20.200
streams. Exactly. He has the vacation movies

00:27:20.200 --> 00:27:22.039
he makes with his friends for Netflix. That's

00:27:22.039 --> 00:27:24.059
the commerce that generates the wealth and keeps

00:27:24.059 --> 00:27:26.579
the lights on for his entire crew. And then,

00:27:26.799 --> 00:27:29.839
because he has that security, he can go off and

00:27:29.839 --> 00:27:33.480
do uncut gems or hustle the prestige films to

00:27:33.480 --> 00:27:36.019
satisfy his artistic soul and remind everyone

00:27:36.019 --> 00:27:38.599
he can really, truly act. And here's the key.

00:27:38.960 --> 00:27:43.000
He funds his art with his commerce, but he actually

00:27:43.000 --> 00:27:45.460
enjoys the commerce too. That's the part people

00:27:45.460 --> 00:27:48.259
miss. He's not miserable making grown -ups. He's

00:27:48.259 --> 00:27:50.640
having a blast with his buddies on a paid vacation.

00:27:50.980 --> 00:27:54.160
It is the ultimate creative hack. He's never

00:27:54.160 --> 00:27:56.660
had to choose. He gets to do both. So here is

00:27:56.660 --> 00:27:58.759
the final provocative thought for you, the listener.

00:27:59.339 --> 00:28:01.740
Sandler has effectively created the perfect work

00:28:01.740 --> 00:28:04.099
-life balance in the most ruthless industry on

00:28:04.099 --> 00:28:06.140
earth. He makes work movies that are actually

00:28:06.140 --> 00:28:07.680
just hanging out with his family and friends,

00:28:07.900 --> 00:28:10.240
and he uses that to fund his passion projects

00:28:10.240 --> 00:28:12.619
every few years. So the question is, is this

00:28:12.619 --> 00:28:15.500
the ultimate hack for... creative life, funding

00:28:15.500 --> 00:28:17.599
your art with your commerce, all while remaining

00:28:17.599 --> 00:28:20.240
the same guy who plays pickup basketball in XXL

00:28:20.240 --> 00:28:23.640
shorts. Maybe tonight, go rewatch Punch Drunk

00:28:23.640 --> 00:28:25.960
Love and look for that technical precision we

00:28:25.960 --> 00:28:29.039
talked about. Look for the method acting underneath

00:28:29.039 --> 00:28:32.640
the blue suit or, you know, just blast the Chinooka

00:28:32.640 --> 00:28:34.440
song and remember how he changed the culture

00:28:34.440 --> 00:28:36.680
with a guitar and a rhyme. There is a lot more

00:28:36.680 --> 00:28:38.579
going on under that baseball cap than people

00:28:38.579 --> 00:28:40.799
give him credit for. Thanks for diving deep with

00:28:40.799 --> 00:28:42.720
us on The Sandman. We'll see you on the next

00:28:42.720 --> 00:28:42.900
one.
