Jonah Hill sits down with Rick Rubin to discuss his evolution from comedic actor to writer-director, exploring his collaborations with Martin Scorsese, Quentin Tarantino, the Coen Brothers, and Gus Van Sant. Hill shares insights from his work on films like Superbad, Moneyball, and his directorial projects including Mid90s, the Stutz documentary, and his latest film Outcome starring Keanu Reeves.

The conversation delves into Hill's personal transformation over the past seven years, including his departure from social media, his therapeutic work with Phil Stutz (documented in The Tools framework), and how becoming a father changed his creative priorities. Hill discusses his production company Strong Baby and his mission to revive theatrical comedy films.

Hill reflects on the craft of filmmaking, from his unconventional acting approach of doing only two long improvisational takes to his early and frequent test screening process. He shares stories about adapting Moneyball with Bennett Miller and his year spent writing with the Beastie Boys on their Beastie Boys Book adaptation.

Directing Styles: Scorsese vs Tarantino's Creative Approaches

Scorsese 'creates this space where the plumbing is so intact, where the infrastructure is so intact that when you walk onto the stage, you can do anything' - Hill

Tarantino operates like 'you are red. Come in and be red in this corner of the painting' - more rigid directorial control

Hill calls 'Once Upon a Time in Hollywood' 'one of the greatest movies I've ever seen my life' and 'a complete masterpiece'

The Social Media Exodus and Creative Freedom

Hill quit social media 4-5 years ago, calling it 'the biggest change that I've had' in his life

'I cringe when I think about when I was on social media as far as like what I posted and the amount of gratification I wanted'

Without social media: 'I stopped thinking, outcome isn't a movie where you're like, what are they doing? I should be doing outcome. Outcome is what you make when you just think, what should I be making?'

Hill's new film Outcome explores how 'even your 12-year-old niece has turned into a middle-aged, scorched, lifelong movie star' due to social media judgment

Phil Stutz and The Therapeutic Documentary Mission

Hill's brother Jordan passed away 7-8 years ago, which was 'probably the impetus of why I started to see Stutz'

The Stutz documentary was designed so 'if you're a kid that doesn't have a lot of money and your parents won't let you do therapy,' they could access therapeutic tools through Netflix

The Tools framework by Phil Stutz provided the foundation for Hill's therapeutic work and documentary approach

Hill surfed in El Salvador where 'all the kids were yelling studs at me' because they had watched and loved the documentary

Unconventional Acting and Directing Methods

Hill does only 'two takes, and they are probably 30-minute takes where they go all over the place' with heavy improvisation

He uses a 'God mic' to pitch new lines to actors during takes: 'I'm writing through a speaker or through an earpiece'

Test screenings happen 'five weeks into a director's cut' - much earlier than typical to identify 'headline problems'

Gus Van Sant's directing style is mysterious: 'I have no idea what he does' but creates an environment where 'you feel safe because it's Gus Van Sant'

The Business of Comedy and Hollywood Reality

'Will couldn't get Anchorman made' despite later massive success - showing how comedy financing has changed

Hill's crisis management character Ira in Outcome is 'a guy with no judgment' by principle because 'his whole livelihood falls apart if he brings an ounce of judgment'

The film industry reality: 'there are things that are real that are way too broad to fit in the movie' - Hollywood is often more outrageous than fiction

Moneyball adaptation challenged assumptions: Hill's father 'didn't believe me because he loved the book' and questioned how it could become a film