Leonardo DiCaprio

Made films the shows talk about.

Wikidata Q38111: matched by corpus:resolve, told apart by the only person by that name on Wikidata.

Counted as actor. The films the hosts said they acted in, which the two lists below run through too: Growing Pains (1985); This Boy's Life (1993); What's Eating Gilbert Grape (1993); Romeo + Juliet (1996); Titanic (1997); The Beach (2000); Catch Me If You Can (2002); Gangs of New York (2002); The Aviator (2004); Blood Diamond (2006); The Departed (2006); Revolutionary Road (2008); Inception (2010); J. Edgar (2011); Django Unchained (2012); The Great Gatsby (2013); The Wolf of Wall Street (2013); The Revenant (2015); Once Upon a Time in Hollywood (2019); Don't Look Up (2021); Killers of the Flower Moon (2023); F1 (2025); One Battle After Another (2025); Body of Lies; Marvin's Room; The Basketball Diaries; Untitled Paul Thomas Anderson film.

Draws on

What the speakers say they, or a film of theirs, drew on. Each is a speaker's account: “the maker said so” when they report the maker's own words, “the host's read” when the read is theirs.

Goodfellas (1990): 3 lines

  1. craft (opening style) · through Killers of the Flower Moon (2023), which they acted in: Goodfellas ⇒ Killers of the Flower Moon (the host's read). The opening tracking shot echoes the Copacabana shot before the film rejects that mode.
    “It was a very long tracking shot through Leo's arrival, which is, you know, gesturing to Copacabana”
    The Big Picture · ‘Killers of the Flower Moon’ Is Astounding · 0:14:19 · Sean Fennessey (0.60 sure it was them)
  2. contrast (inverts) · through Killers of the Flower Moon (2023), which they acted in: Goodfellas ⇒ Killers of the Flower Moon (the host's read). Same crimes by white men but with no romance or good life, a deliberate answer to Goodfellas' seductiveness.
    “there's a romance to Goodfellas that does not exist here.”
    The Big Picture · ‘Killers of the Flower Moon’ Is Astounding · 0:28:46 · Amanda Dobbins (0.50 sure it was them)
  3. unmapped (narration trick) · through Killers of the Flower Moon (2023), which they acted in: Goodfellas ⇒ Killers of the Flower Moon (the host's read). Molly's voiceover recalls Karen taking over narration in Goodfellas.
    “Goodfellas does this. There's a moment when Karen takes over the narration.”
    The Big Picture · ‘Killers of the Flower Moon’ Is Astounding · 1:08:58 · Sean Fennessey (0.50 sure it was them)

Titanic (1997): 2 lines, within their own work

  1. theme (rejects persona) · them, directly: Titanic ⇒ Leonardo DiCaprio (the host's read). His broken, dim characters read as a rejection of Jack in Titanic and the matinee-idol image.
    “maybe all of this is a one long rejection of Jack from Titanic”
    The Big Picture · ‘Killers of the Flower Moon’ Is Astounding · 0:27:38 · Sean Fennessey (0.50 sure it was them)
  2. lineage (callback) · through Killers of the Flower Moon (2023), which they acted in: Titanic ⇒ Killers of the Flower Moon (the host's read). The car make-out scene is a funny Titanic callback.
    “I thought there was a really funny callback to Titanic when they're making out in the car.”
    The Big Picture · ‘Killers of the Flower Moon’ Is Astounding · 0:35:48 · Amanda Dobbins (0.50 sure it was them)

Apocalypse Now (1979): 1 line

  1. lineage (visual influence) · through Once Upon a Time in Hollywood (2019), which they acted in: Apocalypse Now ⇒ Once Upon a Time in Hollywood (the host's read). The dogs at Spahn Ranch play the role of the Duvall helicopters, constantly present and disorienting.
    “He wanted the dogs to be the helicopters.”
    The Rewatchables · ‘Once Upon a Time … in Hollywood’ Live From Sundance With Bill Simmons, Sean Fennessey, and Chris Ryan · 0:37:25 · Bill Simmons (0.50 sure it was them)

Bob & Carol & Ted & Alice (1969): 1 line

  1. lineage (influence) · through Once Upon a Time in Hollywood (2019), which they acted in: Bob & Carol & Ted & Alice ⇒ Once Upon a Time in Hollywood (the maker said so). Tarantino said Bob & Carol & Ted & Alice influenced the characters, looks, and scenery.
    “Quinn said Bob and Carol and Ted Alice was a big influence on this movie”
    The Rewatchables · ‘Once Upon a Time … in Hollywood’ Live From Sundance With Bill Simmons, Sean Fennessey, and Chris Ryan · 1:09:23 · Chris Ryan (0.50 sure it was them)

Boiler Room (2000): 1 line

  1. lineage (lineage) · through The Wolf of Wall Street (2013), which they acted in: Boiler Room ⇒ The Wolf of Wall Street (the host's read). Koppelman says Boiler Room informed Wolf, being the fictional version of Jordan Belfort's story.
    “Boiler Room really informed Wolf of Wall Street because Boiler Room was the fictional version of Jordan's story”
    The Rewatchables · ‘Margin Call’ With Bill Simmons, Ryen Russillo, and Brian Koppelman · 0:25:01 · Brian Koppelman (0.90 sure it was them)

Django (1966): 1 line

  1. career (career) · through Django Unchained (2012), which they acted in: Django ⇒ Django Unchained (the host's read). Django is a better rewatch now because Tarantino later made Django Unchained.
    “Django is a better rewatch now because he made Django unchained.”
    The Rewatchables · ‘Reservoir Dogs’ With Bill Simmons, Sean Fennessey, and Chris Ryan · 0:48:01 · Chris Ryan (0.50 sure it was them)

Eric Roth: 1 line

  1. unmapped (tribute) · through The Great Gatsby (2013), which they acted in: Eric Roth ⇒ The Great Gatsby (the host's read). Roth named the love interest Daisy as a tribute to Gatsby.
    “He calls the love interest daisy as a tribute to the Great Gatsby.”
    Blank Check — Patreon · The Curious Case of Benjamin Button with Richard Lawson (Ad-Free) · 0:42:11 · unknown (0.30 sure it was them)

Francis Bacon: 1 line

  1. unmapped (painting reference) · through The Wolf of Wall Street (2013), which they acted in: Francis Bacon ⇒ The Wolf of Wall Street (the host's read). Bacchanal tableaux reference the Last Supper and Francis Bacon.
    “Sometimes it's the last supper. Sometimes it's Francis Bacon and like the disgusting nature of the human soul.”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:16:25 · unknown (0.40 sure it was them)

Hayao Miyazaki: 1 line

  1. lineage (influence) · them, directly: Hayao Miyazaki ⇒ Leonardo DiCaprio (the host's read). Miyazaki's planet-degradation themes were a critical influence on DiCaprio becoming an environmental activist.
    “Miyazaki is one of the critical influences on DiCaprio becoming such an aggressive environmental activists”
    The Big Picture · Physical Media Strikes Back With Tim Simons · 1:19:29 · Sean Fennessey (0.55 sure it was them)

Infernal Affairs (2002): 1 line

  1. lineage (remake source) · through The Departed (2006), which they acted in: Infernal Affairs ⇒ The Departed (the host's read). The Departed is a remake of the Hong Kong film Infernal Affairs, which is tighter.
    “It was called Infernal Affairs, the Hark Kong one?”
    The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:59:09 · Chris Ryan (0.50 sure it was them)

Lee Van Cleef: 1 line

  1. lineage (source of a detail) · through Once Upon a Time in Hollywood (2019), which they acted in: Lee Van Cleef ⇒ Once Upon a Time in Hollywood (the maker said so: he told me; I asked Quentin about it). The painting of Rick in the driveway came from Tarantino finding a giant Lee Van Cleef painting in the actor's garage while scouting.
    “that's why I put a painting of Rick in the driveway.”
    The Rewatchables · ‘Once Upon a Time … in Hollywood’ Live From Sundance With Bill Simmons, Sean Fennessey, and Chris Ryan · 0:44:51 · Chris Ryan (0.50 sure it was them)

Leonardo DiCaprio: 1 line, within their own work

  1. industry (financing / star power) · through The Wolf of Wall Street (2013), which they acted in: Leonardo DiCaprio ⇒ The Wolf of Wall Street (the host's read). Leo raised the money and attached Scorsese and the cast, which let an extreme film get made without a studio.
    “the idea that it was DiCaprio, who went out and raised the funds to get this movie made”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:11:02 · unknown (0.40 sure it was them)

Martin Donnelly: 1 line

  1. craft (craft) · through F1 (2025), which they acted in: Martin Donnelly ⇒ F1 (the host's read). The crash that ends Sonny's career was based on Donnelly's real crash, and he advised on the film.
    “The crash that ended, Sonny's career was based on the actual crash of Martin Donnelly in the 1990s Spanish Grand Prix.”
    The Rewatchables · ‘F1’ With Bill Simmons, Chris Ryan, and Van Lathan · 1:25:28 · Bill Simmons (0.50 sure it was them)

Paradise Lost (Milton): 1 line

  1. theme (literary echo) · through The Wolf of Wall Street (2013), which they acted in: Paradise Lost (Milton) ⇒ The Wolf of Wall Street (the host's read). Belfort descending into hell as the lights change reads as Paradise Lost.
    “Yeah, that's the Paradise Lost, you know, yeah.”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:16:07 · unknown (0.40 sure it was them)

Pulp Fiction (1994): 1 line

  1. lineage (lineage) · through Once Upon a Time in Hollywood (2019), which they acted in: Pulp Fiction ⇒ Once Upon a Time in Hollywood (the host's read). Marcellus's you-pride-only-hurts speech to Butch is the same speech Pacino gives DiCaprio in Once Upon a Time in Hollywood.
    “And it's the same speech that Pacino gives DiCaprio at Rousseau and Frank in Once Upon a Time in Hollywood.”
    The Rewatchables · ‘Pulp Fiction’ (Part 2) With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:17:32 · unknown (0.00 sure it was them)

Robert De Niro: 1 line

  1. lineage (influence) · them, directly: Robert De Niro ⇒ Leonardo DiCaprio (the maker said so: a story Leo tells). Leo met De Niro on This Boy's Life, watched every De Niro movie and got hip to Scorsese through them.
    “He met De Niro working on this boy's life and he watched every De Niro movie and he really connected with the De Niro Scorsese movies.”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:27:15 · unknown (0.40 sure it was them)

Rocky IV (1985): 1 line

  1. theme (theme) · through F1 (2025), which they acted in: Rocky IV ⇒ F1 (the host's read). Sonny and Kate's beer scene cuts into an old-school versus new-school training montage like Rocky IV.
    “Right into the Rocky 4 training montage”
    The Rewatchables · ‘F1’ With Bill Simmons, Chris Ryan, and Van Lathan · 0:48:10 · Bill Simmons (0.50 sure it was them)

Scarface (1983): 1 line

  1. lineage (homage) · through The Departed (2006), which they acted in: Scarface ⇒ The Departed (the host's read). The film has references to classic gangster films like the original Scarface that feel like pastiche.
    “there's a couple of references in this movie to classic gangster films like the original Scarface”
    The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:45:24 · Chris Ryan (0.50 sure it was them)

The Hateful Eight (2015): 1 line

  1. theme (opening echo) · through Once Upon a Time in Hollywood (2019), which they acted in: The Hateful Eight ⇒ Once Upon a Time in Hollywood (the host's read). The slow pan out to the painting of Rick echoes the slow pan out to the Jesus statue in Hateful Eight.
    “It's very similar to the beginning of Hateful 8, where there's this very slow panout and it's like a Jesus Christ statue.”
    The Rewatchables · ‘Once Upon a Time … in Hollywood’ Live From Sundance With Bill Simmons, Sean Fennessey, and Chris Ryan · 0:44:05 · Chris Ryan (0.50 sure it was them)

The Texas Chain Saw Massacre (1974): 1 line

  1. lineage (visual influence) · through Once Upon a Time in Hollywood (2019), which they acted in: The Texas Chain Saw Massacre ⇒ Once Upon a Time in Hollywood (the host's read). Tarantino wanted the Spahn Ranch sequence to feel like Texas Chain Saw Massacre.
    “Tarantino wanted it to look like the Texas Chainsaw Massacre and had his crew research, Texas Chant, and the whole feel of it and how desolate it was.”
    The Rewatchables · ‘Once Upon a Time … in Hollywood’ Live From Sundance With Bill Simmons, Sean Fennessey, and Chris Ryan · 0:37:06 · Bill Simmons (0.50 sure it was them)

The Wolf of Wall Street (2013): 1 line, within their own work

  1. lineage (influence / humor) · through One Battle After Another (2025), which they acted in: The Wolf of Wall Street ⇒ One Battle After Another (the host's read). Scorsese influenced PTA, and the uncomfortable-laughter humor of Wolf is very PTA.
    “Scorsese is a huge influence on all filmmakers, including PTA, and there is a, like, a really screwed up level to the humor in this movie that is that is very PTA as well”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:16:54 · unknown (0.40 sure it was them)

Twister (1996): 1 line

  1. industry (industry) · through Titanic (1997), which they acted in: Twister ⇒ Titanic (the host's read). Twister started a playbook of putting not-yet-A-list leads in a spectacle, which Titanic and later Star Wars followed.
    “It became a playbook for it.”
    The Rewatchables · ‘Twister’ With Bill Simmons, Chris Ryan, and Van Lathan · 1:54:01 · Bill Simmons (0.40 sure it was them)

Wanted: Dead or Alive (1958): 1 line

  1. lineage (based on) · through Once Upon a Time in Hollywood (2019), which they acted in: Wanted: Dead or Alive ⇒ Once Upon a Time in Hollywood (the host's read). Bounty Law is based on Steve McQueen's Wanted Dead or Alive.
    “Bounty Lostar, which was based on Wanted Dead or Alive with Steve McQueen”
    The Rewatchables · ‘Once Upon a Time … in Hollywood’ Live From Sundance With Bill Simmons, Sean Fennessey, and Chris Ryan · 0:16:14 · Bill Simmons (0.50 sure it was them)

Drawn on by

What the speakers say drew on them or a film of theirs, marked the same way.

Avatar (2009): 2 lines

  1. career (career) · through Titanic (1997), which they acted in: Titanic ⇒ Avatar (the host's read). Avatar could only be made because Titanic gave Cameron the clout.
    “I'd never have gotten to make it if he hadn't made Titanic.”
    The Big Picture · The Great ‘Avatar’ Debate with Blank Check’s Griffin Newman and David Sims · 1:09:04 · unknown (0.40 sure it was them)
  2. verdict (verdict) · through Titanic (1997), which they acted in: Titanic ⇒ Avatar (the host's read). Titanic made Cameron so successful that Hollywood let him do anything.
    “needed to have this extraordinary amount of success over these decades to conceive an execute of something so crazy as Avatar.”
    The Big Picture · The Great ‘Avatar’ Debate with Blank Check’s Griffin Newman and David Sims · 1:45:16 · unknown (0.40 sure it was them)

Killers of the Flower Moon (2023): 1 line, within their own work

  1. lineage (callback) · through Titanic (1997), which they acted in: Titanic ⇒ Killers of the Flower Moon (the host's read). The car make-out scene is a funny Titanic callback.
    “I thought there was a really funny callback to Titanic when they're making out in the car.”
    The Big Picture · ‘Killers of the Flower Moon’ Is Astounding · 0:35:48 · Amanda Dobbins (0.50 sure it was them)

Leonardo DiCaprio: 1 line, within their own work

  1. theme (rejects persona) · through Titanic (1997), which they acted in: Titanic ⇒ Leonardo DiCaprio (the host's read). His broken, dim characters read as a rejection of Jack in Titanic and the matinee-idol image.
    “maybe all of this is a one long rejection of Jack from Titanic”
    The Big Picture · ‘Killers of the Flower Moon’ Is Astounding · 0:27:38 · Sean Fennessey (0.50 sure it was them)

Master and Commander: The Far Side of the World (2003): 1 line

  1. unmapped (shared-technology) · through Titanic (1997), which they acted in: Titanic ⇒ Master and Commander: The Far Side of the World (the host's read). The film exists because James Cameron's Mexican Titanic tank, with a gimbal, was still usable for the ship set.
    “James Cameron had done the legwork to build out the system to be able to basically shoot this on a gimbal in a tank of a proper set.”
    Blank Check with Griffin & David · Master and Commander: The Far Side of the World with John Hodgman · 1:30:47 · David Sims (0.50 sure it was them)

One Battle After Another (2025): 1 line, within their own work

  1. lineage (influence / humor) · through The Wolf of Wall Street (2013), which they acted in: The Wolf of Wall Street ⇒ One Battle After Another (the host's read). Scorsese influenced PTA, and the uncomfortable-laughter humor of Wolf is very PTA.
    “Scorsese is a huge influence on all filmmakers, including PTA, and there is a, like, a really screwed up level to the humor in this movie that is that is very PTA as well”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:16:54 · unknown (0.40 sure it was them)

The Fresh Prince of Bel-Air (1990): 1 line

  1. lineage (ripped off) · through Growing Pains (1985), which they acted in: Growing Pains ⇒ The Fresh Prince of Bel-Air (the host's read). Bill's hot take: Fresh Prince's famous Uncle Phil scene was lifted from a Growing Pains episode with Leo.
    “was actually ripped off from growing pains and Leo”
    The Rewatchables · ‘What About Bob?’ With Bill Simmons, Sean Fennessey, and Van Lathan · 1:06:03 · Bill Simmons (0.80 sure it was them)

The Wolf of Wall Street (2013): 1 line, within their own work

  1. industry (financing / star power) · them, directly: Leonardo DiCaprio ⇒ The Wolf of Wall Street (the host's read). Leo raised the money and attached Scorsese and the cast, which let an extreme film get made without a studio.
    “the idea that it was DiCaprio, who went out and raised the funds to get this movie made”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:11:02 · unknown (0.40 sure it was them)

What the speakers said they did

Acting (62) everyone in acting

Other (3) everyone in other

What was said about them, by kind

career (4)

  1. career (career): Brad Pitt → Leonardo DiCaprio. Pitt never aligned with a single auteur the way DiCaprio did.
    “So in the way that Leo said, you know what?”
    The Rewatchables · ‘F1’ With Bill Simmons, Chris Ryan, and Van Lathan · 0:20:20 · Chris Ryan (0.50 sure it was them)
  2. career (career kinship): Paul Newman → Leonardo DiCaprio. Leo's careful choice of movies and parts reminds Bill of Newman's.
    “the way Leo just very carefully picks his movies and his parts reminds me of Newman.”
    The Rewatchables · ‘The Color of Money’ With Bill Simmons, Chris Ryan, and Sean Fennessey · 0:07:49 · Bill Simmons (0.80 sure it was them)
  3. career (career turning point): Leonardo DiCaprio → Titanic. After Titanic Leo made it his mission to work with Scorsese.
    “he made it his mission after Titanic to get Scorsese movies.”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:27:23 · unknown (0.40 sure it was them)
  4. career (career): James Cameron → Leonardo DiCaprio. Cameron helped launch Leo.
    “he helped launch Leo.”
    The Big Picture · The Great ‘Avatar’ Debate with Blank Check’s Griffin Newman and David Sims · 0:21:05 · unknown (0.40 sure it was them)

craft (1)

  1. craft (craft): Leonardo DiCaprio → J. Gianoni. Leo's Boston accent coach on the film is named as J. Gianoni.
    “Leo's Boston accent coach was named J. Gianoni.”
    The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:29:32 · Chris Ryan (0.50 sure it was them)

industry (2)

  1. industry (same studio campaign): Leonardo DiCaprio → Blood Diamond. Leo was campaigned for Blood Diamond instead of The Departed because one studio made both.
    “Leo got nominated for Blood Diamond because the same studio did Blood Diamond and the Departed.”
    The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:08:22 · Bill Simmons (0.70 sure it was them)
  2. industry (financing / star power): The Wolf of Wall Street → Leonardo DiCaprio. Leo raised the money and attached Scorsese and the cast, which let an extreme film get made without a studio.
    “the idea that it was DiCaprio, who went out and raised the funds to get this movie made”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:11:02 · unknown (0.40 sure it was them)

lineage (2)

  1. lineage (influence): Leonardo DiCaprio → Robert De Niro. Leo met De Niro on This Boy's Life, watched every De Niro movie and got hip to Scorsese through them.
    “He met De Niro working on this boy's life and he watched every De Niro movie and he really connected with the De Niro Scorsese movies.”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:27:15 · unknown (0.40 sure it was them)
  2. lineage (influence): Hayao Miyazaki → Leonardo DiCaprio. Miyazaki's planet-degradation themes were a critical influence on DiCaprio becoming an environmental activist.
    “Miyazaki is one of the critical influences on DiCaprio becoming such an aggressive environmental activists”
    The Big Picture · Physical Media Strikes Back With Tim Simons · 1:19:29 · Sean Fennessey (0.55 sure it was them)

people (3)

  1. people (third collaboration): Martin Scorsese → Leonardo DiCaprio. Leo took the movie seriously partly because this was his third film with Scorsese and his chops were not yet proven.
    “Martin Scorsese directed me for the 3rd time, and I'm having a good career, but I haven't really proven my chops yet.”
    The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:13:05 · Bill Simmons (0.60 sure it was them)
  2. people (reunion): Leonardo DiCaprio → Robert De Niro. First on-screen pairing since This Boy's Life (1993), with Marvin's Room also a joint credit.
    “since De Niro and Leo appeared on screen together, since this boy's life in 1993.”
    The Big Picture · ‘Killers of the Flower Moon’ Is Astounding · 0:06:42 · Sean Fennessey (0.50 sure it was them)
  3. people (performance): Once Upon a Time in Hollywood → Leonardo DiCaprio. DiCaprio is the obvious best leading performance of the summer.
    “Well, I, the obvious one is Leonardo DiCaprio.”
    The Big Picture · The Future of ‘Star Wars,’ Marvel, Pixar, and Disney’s Movie Monopoly. Plus: Our Summer Movie Awards and Paul Downs Colaizzo on ‘Brittany Runs a Marathon’ | The Big Picture · 0:20:28 · Chris Ryan (0.50 sure it was them)

programming (1)

  1. programming (iconic pairing): Leonardo DiCaprio → Robert De Niro. Ryan predicts Rick and Cliff will be tied to Brad and Leo as Michael Corleone is to Pacino and LaMotta to De Niro.
    “we will like associate Rick and Cliff with Brad and Leo the way we do, you know, Michael Corleone with Al Pacino or, you know, like Jake Lamano with Robert De Niro.”
    The Rewatchables · ‘Once Upon a Time … in Hollywood’ Live From Sundance With Bill Simmons, Sean Fennessey, and Chris Ryan · 0:04:40 · Chris Ryan (0.70 sure it was them)

theme (1)

  1. theme (rejects persona): Leonardo DiCaprio → Titanic. His broken, dim characters read as a rejection of Jack in Titanic and the matinee-idol image.
    “maybe all of this is a one long rejection of Jack from Titanic”
    The Big Picture · ‘Killers of the Flower Moon’ Is Astounding · 0:27:38 · Sean Fennessey (0.50 sure it was them)

unmapped (4)

  1. unmapped (dropped out for): Leonardo DiCaprio → The Good Shepherd. Leo left The Good Shepherd to do The Departed, and De Niro turned down Sheen's part to do it.
    “Leo dropped out of the Good Shepherd to do the departed.”
    The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:29:14 · Bill Simmons (0.60 sure it was them)
  2. unmapped (unsympathetic subjects): J. Edgar → Leonardo DiCaprio. Leo has played J. Edgar Hoover and other complicated, not-nice figures in American history.
    “he had previously also just played Jager Hoover. He clearly is not afraid of complicated, not nice people in American history.”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:28:32 · unknown (0.40 sure it was them)
  3. unmapped (introduced): Spirited Away → Leonardo DiCaprio. DiCaprio introduced Scorsese to Spirited Away.
    “he was like, but, you know, I did put you onto Miyazaki and specifically spirited away.”
    The Big Picture · Physical Media Strikes Back With Tim Simons · 1:19:08 · Sean Fennessey (0.55 sure it was them)
  4. unmapped (long-running want): Leonardo DiCaprio → Boogie Nights. PTA wanted DiCaprio for Boogie Nights and has been trying to cast him since.
    “PTA wanted Leo for boogie nights.”
    The Big Picture · Best Picture Power Rankings and a ‘Poor Things’ Deep Dive. Plus: Julianne Moore and Todd Haynes! · 0:08:21 · Sean Fennessey (0.65 sure it was them)

verdict (5)

  1. verdict (favorite performances): Leonardo DiCaprio → The Wolf of Wall Street. This, Wolf and Django are Ryan's three favorite Leo performances, not The Revenant.
    “I would say this Wolf and Django are my 3 favorite Leo performances.”
    The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:09:01 · Chris Ryan (0.60 sure it was them)
  2. verdict (best performance candidate): Django Unchained → Leonardo DiCaprio. Calvin Candie is offered as one of the great villains of the last 20 years and Leo's bravest turn.
    “As Calvin Candy, one of the great villains from the last 20 years, and he is, he just pulls no punches in that movie.”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:28:11 · unknown (0.40 sure it was them)
  3. verdict (best performance candidate): Once Upon a Time in Hollywood → Leonardo DiCaprio. A host argues Once Upon a Time is probably Leo's best performance, citing the Bounty Law trailer breakdown.
    “I could argue that that once upon a time, probably, is his, is his best performance.”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:29:08 · unknown (0.40 sure it was them)
  4. verdict (verdict): Catch Me If You Can → Leonardo DiCaprio. Catch Me If You Can is Leo at his best but falls apart in the last half hour.
    “It falls apart with about a half hour to go.”
    The Big Picture · Steven Spielberg's Top 5 Movies With Bill Simmons and Chris Ryan | The Big Picture (Ep. 57) · 0:55:49 · Bill Simmons (0.70 sure it was them)
  5. verdict (verdict): Leonardo DiCaprio → Once Upon a Time in Hollywood. Possibly his favorite DiCaprio performance, near career-best.
    “Maybe my favorite Leonardo DiCaprio performance.”
    Blank Check — Patreon · The Fifth Annual Blank Check Awards with Joe Reid (Ad-Free) · 0:56:54 · Griffin Newman (0.45 sure it was them)

Fun items about them

  1. fun, about Leonardo DiCaprio: The trailer meltdown was improvised and was Leo's idea, which he brought to Tarantino.
    “It's also all improvised. It's not written. This was all Leo's idea, which he brought to Quentin, and they decided it would be a good idea.”
    The Rewatchables · ‘Once Upon a Time … in Hollywood’ Live From Sundance With Bill Simmons, Sean Fennessey, and Chris Ryan · 0:35:47 · Bill Simmons (0.40 sure it was them)
  2. fun, about Leonardo DiCaprio: The flamethrower flashback uses Leo's genuine reaction to the heat; Tarantino kept it.
    “Apparently that was Leo's genuine reaction to using it. It was too hot. And Tarantino thought it was hilarious”
    The Rewatchables · ‘Once Upon a Time … in Hollywood’ Live From Sundance With Bill Simmons, Sean Fennessey, and Chris Ryan · 1:04:55 · Bill Simmons (0.40 sure it was them)
  3. fun, about Leonardo DiCaprio: Leo owns the Maltese Falcon that Sharon Tate holds in the bookstore and lent it to the film.
    “The Maltese Falcon, which Sharon Tate holds in the bookstore, is now owned by Leo DiCaprio.”
    The Rewatchables · ‘Once Upon a Time … in Hollywood’ Live From Sundance With Bill Simmons, Sean Fennessey, and Chris Ryan · 1:06:51 · Bill Simmons (0.40 sure it was them)
  4. fun, about Leonardo DiCaprio: The scene where Leo is killed made the theater gasp like at a sporting event, the Red Wedding of this movie.
    “It's the red wedding of this movie.”
    The Rewatchables · ‘The Departed’ With Bill Simmons and Chris Ryan · 0:10:58 · Chris Ryan (0.55 sure it was them)
  5. fun, about Leonardo DiCaprio: The film was financed independently because no studio would have allowed Leo to blow cocaine out of a prostitute's behind in the first five minutes.
    “I don't think a studio would have allowed for Leo to blow cocaine out of a prostitute's ass in the 1st 5 minutes of the movie.”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:10:33 · unknown (0.40 sure it was them)
  6. fun, about Leonardo DiCaprio: Leo counted at 18 feature films this century, and One Battle will be his 19th or 20th, which became a counting joke.
    “One battle after another will be either his 19th or 20th feature film this century.”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:25:34 · unknown (0.40 sure it was them)
  7. fun, about Leonardo DiCaprio: The wedding dance to a 60-year-old blues song: a host did not know Leo could dance and loved how loose he is.
    “I had forgotten the dancing at the wedding. I love that.”
    The Big Picture · The 25 Best Movies of the Century: No. 11 - 'The Wolf of Wall Street’ · 0:29:43 · unknown (0.40 sure it was them)
  8. fun, about Leonardo DiCaprio: Letterboxd conversation: DiCaprio says he put Scorsese onto Spirited Away.
    “And then Scorsese is like, you did.”
    The Big Picture · Physical Media Strikes Back With Tim Simons · 1:19:24 · Sean Fennessey (0.55 sure it was them)