Film credit
Leonardo DiCaprio
Also referred to as Leo, DiCaprio, Leo DiCaprio, Leonardo Capriano
Stats
- Episodes featuring their films
- 8
- Movies in this archive
- 8
Rewatchables episodes featuring Leonardo DiCaprio’s films
Once Upon a Time in Hollywood
2019 film
Bill Simmons · Sean Fennessey · Chris Ryan
Aired February 6, 2020
The Wolf of Wall Street
2013 film
Sean Fennessey · Chris Ryan · Ryen Russillo
Aired December 3, 2019
Mentioned in discussions
Casting What-Ifs
Kate Hudson as Mary Jane; Tig Notaro in the check-in role; Elizabeth Banks as Mary Jane; James Franco as Peter; Nicolas Cage as Norman Osborn
In the discussion (5)
- Kate Hudson reportedly turned down Mary Jane to make The Four Feathers; Alicia Witt and other actresses were also considered. — Van Lathan
- Many young white actors, including Freddie Prinze Jr. and Leonardo DiCaprio, were reportedly considered for Peter. — Van Lathan
- Octavia Spencer's wrestling check-in role was reportedly offered to Tig Notaro, who was then asked to audition and lost it. — Van Lathan
- Elizabeth Banks reportedly sought Mary Jane, was called too old, and got the Betty Brant role instead; James Franco reportedly auditioned for Peter. — Charles Holmes
- Nicolas Cage as Norman Osborn is raised as the biggest what-if and judged an awkward fit next to James Franco. — Van Lathan
In the discussion (1)
- Leonardo DiCaprio is named and agreed on, since he became the biggest star of the last 25 years, even though it feels odd to deny James Cameron. — Bill Simmons
Podcast choices
- Speaker not identified
- Leonardo DiCaprio
- Speaker not identified
- Leonardo DiCaprio
Probably Unanswerable Questions
Rose's fate at the end; the car hand-print position; climate change and icebergs; Jack and Rose's longevity; DiCaprio passing on Boogie Nights
In the discussion (5)
- Whether Rose is alive and dreaming or dead at the end; Cameron leaves it open. — Bill Simmons
- What sex position produced the hand on the car window without his head in frame, with a joking MythBusters-style reenactment proposal. — Bill Simmons
- Whether the film is an argument that climate change would prevent icebergs, asked as a joke. — Bill Simmons
- How long Jack and Rose would have lasted if both survived; both hosts think they would marry. — Bill Simmons
- DiCaprio turning down Boogie Nights for Titanic is judged a good call; Paul Thomas Anderson reportedly agreed it worked out, and Dirk Diggler is called Wahlberg's Apex Mountain. — Bill Simmons
Apex Mountain
Leonardo DiCaprio, disputed; James Cameron; Billy Zane; expensive bad-buzz movies; heroes from Wisconsin; icebergs; disaster movies
In the discussion (6)
- DiCaprio is a yes because he became the biggest star in the world; 2006, with Blood Diamond and The Departed, is the alternative. — Bill Simmons
- The counterargument is that people do not associate DiCaprio primarily with Titanic, and The Departed era is offered as his better Apex. — Bill Simmons
- Winslet is probably not, because of her mid-2000s run culminating in the 2008 Oscar for The Reader. — Bill Simmons
- Cameron is a yes even though he later beat it, because the film was a critical and financial peak comparable to Gone with the Wind. — Bill Simmons
- Billy Zane is a yes; for the name Fabrizio, the Godfather character who blew up Apollonia's car is preferred. — Bill Simmons
- Expensive bad-buzz movies peak here, beating The Godfather; heroes from Wisconsin (Jack), icebergs, and disaster movies are yes, Picasso probably not. — Bill Simmons
Recasting Couch
Young Ben Affleck as Cal
In the discussion (2)
- 1997 Matt Damon of School Ties is proposed for Cal but judged too similar to DiCaprio; Zane works as a dark, East Coast contrast. — Van Lathan
- Brendan Fraser is floated but may be too nice; young Ben Affleck is judged a perfect fit with a size difference from DiCaprio. — Van Lathan
Casting What-Ifs
Johnny Depp; Jared Leto; Claire Danes; Jeremy Sisto; Billy Crudup; Gwyneth Paltrow; Winona Ryder; Matthew McConaughey; Enya; Robert De Niro
In the discussion (8)
- Johnny Depp reportedly turned down Jack over the script; Jared Leto was reportedly favored but would not audition, and the actress transcribed as Claire Daines was supposedly wanted for Rose. — Bill Simmons
- Jeremy Sisto auditioned multiple times and is lamented as never finding the right part; Billy Crudup was considered but was committed to Without Limits. — Bill Simmons
- DiCaprio excelled in testing, and Winslet reportedly lobbied hard, telling Cameron to pick DiCaprio even if not her. — Bill Simmons
- Gwyneth Paltrow and Winona Ryder were reportedly in the mix; Paltrow might have been decent but is judged too regal, and Winslet remains the best choice. — Bill Simmons
- The Cal role was reportedly offered to Matthew McConaughey, who turned it down. — Bill Simmons
- McConaughey as Cal is judged unworkable; a report that he was also offered Jack is doubted. — Bill Simmons
- Cameron reportedly wanted Enya for the music before settling on Celine Dion. — Bill Simmons
- Robert De Niro was reportedly offered Captain Smith but declined due to a gastrointestinal infection; he would have been fun in the role. — Bill Simmons
What’s Aged the Best?
Leo and Kate; James Cameron; the score; the band; the mother reading to her children; the Celine Dion song; Cal's evil line; Andrews and Smith sports comparisons; Bill Paxton; shipwreck-search TV; the Rose YouTube video
In the discussion (9)
- Leo and Kate, given their subsequent careers, are the number one answer, with James Cameron added. — Bill Simmons
- The score and its variations of the song are praised, and the film is likened to a first-class dinner where every detail was considered. — Bill Simmons
- Cameron reportedly sketched how people would behave facing death; the band playing to the end is another aged-best pick. — Bill Simmons
- The mother reading to her children below deck, reportedly played by the actress from Terminator 2, is recalled as emotionally brutal. — Van Lathan
- The Celine Dion song is one of the most identifiable songs ever attached to a movie; Winslet's nude scene is also cited as a generational milestone. — Bill Simmons
- Cal's line when Rose breaks away the second time is called a great evil-guy line. — Bill Simmons
- Mr. Andrews and Captain Smith are compared to the executive realizing the Westbrook trade failed and to Frank Vogel. — Bill Simmons
- Bill Paxton is fondly remembered, and the salvage crew's work now resembles History Channel shipwreck and search programs, called Titanic spin-off content. — Van Lathan
- The hosts' YouTube video about Rose is jokingly expected to age well, with a call for Rachel Lindsay's take on Higher Learning. — Bill Simmons
Most Rewatchable Scene
Dinner party and the sinking; Jack and Rose at the bow
In the discussion (11)
- Nothing from the first 21 minutes qualifies; the rescue at the stern and Jack nearly being blamed is offered, with an audio clip.
- The dinner party, with Jack's borrowed tuxedo from Kathy Bates, is called the best scene before the sinking. — Bill Simmons
- In the dinner scene, Jack's speech that life is a gift, played as a clip, is called DiCaprio's best scene and the Oscar clip he should have had. — Bill Simmons
- A list of candidates includes the embrace at the bow, the drawing scene (reportedly the first scene the leads filmed), the chase, and the car scene with the hand on the window. — Bill Simmons
- The iceberg collision is praised with a clip, and the ship passing the iceberg prompts discussion of practical effects versus visible CGI and a brutal shoot. — Van Lathan
- Rose breaking away from Cal, his drawing jab, and her spitting in his face are recalled; the line is remembered paralyzing a Baton Rouge theater. — Bill Simmons
- The axe scene, the ship breaking and turning into a horror movie, and Captain Smith's final scene with 120 tons of water are also listed. — Bill Simmons
- The final return to the restored ship and reunion on the staircase is called breathtaking despite the earlier criticism of Rose. — Bill Simmons
- One final choice is the dinner party plus the ship sinking and tipping over. — Bill Simmons
- The other side adds Cal turning gunman, likened to O.J. Simpson, and the steerage party showing Rose can live in Jack's world. — Van Lathan
- The second final choice is Jack and Rose together at the bow, clarified as not the earlier king-of-the-world line.
In the discussion (8)
- DeCaprio is proposed, as last time, followed by "Yeah. I agree." — Bill Simmons
- Martin Scorsese, who won Best Director at the Academy Awards. — Sean Fennessey
- Pushback: the question is who won the movie, not who made the best movie, and Leo wins it.
- The Scorsese case: a $300 million movie, the two biggest movie stars playing opposite each other, and the long-awaited Best Picture and Best Director. — Sean Fennessey
- Still Leo: one of the most important actors of a lifetime, who proved in two and a half hours that he could do anything. — Bill Simmons
- Thought experiment: Leo needed this movie for his stretch but was already Leo; without it Scorsese likely never wins Best Picture or Director and becomes Charles Barkley.
- Sides with Sean's pick of Scorsese. — Craig Horlbeck
- The tally is tied two to two; the Scorsese case is seen from a career standpoint, but Leo wins the movie; both did it, and there are many winners.
Podcast choices
- Speaker not identified
- Leonardo DiCaprio
- Speaker not identified
- Leonardo DiCaprio
In the discussion (6)
- Colin's impotence ties to his whole life being a lie and a performance.
- His "I'm fucking Irish" speech to Madeline is judged sincere, his most Billy moment, with a Jets joke.
- Whose baby is Madeline carrying: one thinks Colin's, others argue Leo's since only Billy is shown having sex with her. — Bill Simmons
- Why Madeline does not turn Colin in despite the evidence; her exit is abrupt. — Bill Simmons
- If Damon and Leo switched parts: worse, since nobody could do Costigan better than DeCaprio, versus Damon could have done it (Courage Under Fire, The Last Duel).
- Why the name Dignam: one of Monaghan's naming flourishes.
Picking Nits
Costigan's bad deal and psychology; death-wish motivation; Queenan and Costello missing the rats; Colin's interrogation interference; the left envelope; the lawyer's tapes; Combat Zone anachronism; two dates of birth; nonexistent apartment
In the discussion (8)
- Why Costigan agreed to such a terrible deal; his split-family psychology and being challenged as a rich boy do not explain it, and his violent history should have kept him out of the academy.
- The tax-free pay written on paper and whether he is a thrill-seeker; one view is a death wish the movie did not sell correctly.
- Which is more unrealistic: Sheen not realizing Damon was the rat despite his calls, or Costello not realizing Leo was. — Bill Simmons
- Damon turning off the interrogation camera and later losing the tail stretches disbelief, partly explained by Badge Dale also working for Costello.
- Costigan sees the Citizens Bank envelope, leaves it displayed and runs, botching the moment despite supposedly high SITs (as transcribed). — Bill Simmons
- What if Costigan never saw the envelope: the movie just ends with more impotent sex. — Sean Fennessey
- Costello's lawyer giving Costigan the tapes is a stretch. — Bill Simmons
- The Patriot Act dates the film to at least 2002, when the porn theaters were gone; Costigan's record shows two dates of birth; the apartment does not exist. — Bill Simmons
Apex Mountain
Dropkick Murphys; Van Morrison's live 'Comfortably Numb'; Kevin Corrigan as cop-magnet cousin
In the discussion (10)
- Leo has a case, with this and Blood Diamond in the same year and merging critical acclaim with blockbusters (Shutter Island, Wolf of Wall Street).
- Matt Damon, no; Scorsese, no, although a case was made for a career apex. — Bill Simmons
- The Dropkick Murphys are a yes: Papelbon used "Shipping Up to Boston" as entrance music and it became the Red Sox song; the Bosstones missed with "The Impression That I Get". — Bill Simmons
- Jack Nicholson, no; Mark Wahlberg, no. — Bill Simmons
- "Comfortably Numb" as a song had bigger moments on its original release, but this Van Morrison live-album version is a yes.
- After not knowing "Comfortably Numb", quizzed to name a Pink Floyd song and answers The Wall. — Craig Horlbeck
- Combat Zone porn theaters are raised, but the area had been cleaned up years before 2006, making them an anachronism; memories of the Combat Zone and a porn theater near the Boston Garden. — Bill Simmons
- Alec Baldwin, no (30 Rock); Southie and extended Boston, no, done better; Vera, no (Conjuring, Up in the Air). — Bill Simmons
- Kevin Corrigan is the apex mountain of being a cop-magnet cousin; the back porch view recalls Charlestown.
- The "Thief's Theme" drive is called a rare great Scorsese hip-hop moment that should have been put in Apex.
Films in the archive
Blood Diamond
2006
Catch Me If You Can
2002
Django Unchained
2012
Once Upon a Time in Hollywood
2019
The Departed
2006
The Wolf of Wall Street
2013
This Boy's Life
1993
Titanic
1997


