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The Italian Job
The Gambler
National Lampoon’s Vacation
Blood Diamond
Blood Diamond
Blood Diamond
Blood Diamond
Blood Diamond
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
Displaying all 8 episodes
Mentioned in discussions
Recasting Couch
Replace Philadelphia; consider Leonardo DiCaprio for Charlie.
In the discussion (3)
Approx. transcript time · 01:23:52Read transcript
- Philadelphia is targeted for replacement, with Boston and Chicago proposed. — Bill Simmons
- Matt Damon and Ben Affleck are briefly considered for Charlie. — Bill Simmons
- Leonardo DiCaprio is the sustained recasting proposal. — Bill Simmons
Casting What-Ifs
DiCaprio and Scorsese initially; Todd Phillips briefly
In the discussion (2)
Approx. transcript time · 00:07:48Read transcript
- Leonardo DiCaprio was reportedly initially attached. — Bill Simmons
- The project initially involved Scorsese, DiCaprio and Monahan; Scorsese departed, Todd Phillips briefly followed, and Wyatt and Wahlberg eventually took over. — Bill Simmons
The Stephen A. Smith Hottest Take Award
Hall as greatest teen actor, disputed; salesman was right; Clark’s infidelity defended, disputed
In the discussion (9)
Approx. transcript time · 00:20:02Read transcript
- Anthony Michael Hall is proposed as the greatest teenage actor based on Vacation, Sixteen Candles, The Breakfast Club, and Weird Science within three years. — Bill Simmons
- River Phoenix and Leonardo DiCaprio are preferred by an opposing view; Robert Downey Jr., Jon Cryer, and Molly Ringwald are also raised, with Ringwald criticized as less varied. — Bill Simmons
- DiCaprio’s This Boy’s Life, What’s Eating Gilbert Grape, Romeo + Juliet, Growing Pains, and The Basketball Diaries are compared, with uncertainty about whether some fall within his teenage years.
- Phoenix’s case includes Stand by Me, The Mosquito Coast, Running on Empty, The Last Crusade, My Own Private Idaho, and Little Nikita.
- The Hall claim is softened toward most successful or beloved rather than best; his consistently welcome presence remains the defense. — Bill Simmons
- Hall’s teenage SNL membership underscores his stature, while later Vacation-series child casting is criticized as inferior. — Bill Simmons
- The salesman was right about the family truckster because it completes the trip and survives an enormous crash.
- Clark’s attempted infidelity is provocatively defended as a response to repeated rejection; the claim of a sexless marriage is disputed and the pool-waitress excuse remains indefensible. — Van Lathan
- Hall’s characters in Vacation, Sixteen Candles, The Breakfast Club and Weird Science are defended as distinct, and he can serve as Chase’s straight man. — Bill Simmons
In the discussion (8)
Approx. transcript time · 01:15:35Read transcript
- Lab-grown diamonds are added as the clearest thing that aged well. — Craig Horlbeck
- The producer had not seen the film and responds positively to its mix of action and difficult subject matter. — Craig Horlbeck
- Modern difficult-topic awards movies are contrasted as smaller and sadder rather than large star vehicles. — Craig Horlbeck
- Kanye West’s Diamonds from Sierra Leone was the producer’s first exposure to conflict diamonds. — Craig Horlbeck
- A modern Zwick might make a documentary because a hundred-million-dollar studio feature is hard to greenlight. — Chris Ryan
- DiCaprio is praised for still using stardom to mount expensive issue-oriented films. — Chris Ryan
- The Siege is used to show how quickly current-affairs films can be overtaken by history. — Chris Ryan
- Global studios’ need for broadly marketable antagonists is cited as another constraint. — Chris Ryan
Podcast choices
- Speaker not identified
- Leonardo DiCaprio
- Speaker not identified
- Leonardo DiCaprio
Probably Unanswerable Questions
Which 2006 Leonardo DiCaprio death scene is best?
In the discussion (3)
Approx. transcript time · 01:13:11Read transcript
- The question compares DiCaprio’s deaths in Blood Diamond and The Departed. — Bill Simmons
- Titanic is added as the iconic death, while The Revenant is briefly and uncertainly queried. — Bill Simmons
- Blood Diamond’s romantic call and final act of protection are weighed against The Departed’s suddenness. — Bill Simmons
In the discussion (3)
Approx. transcript time · 01:10:29Read transcript
- DiCaprio is the immediate choice, though his stronger case across both 2006 movies is emphasized. — Bill Simmons
- Zwick is proposed for directing the unusually ambitious production. — Chris Ryan
- The panel argues for an award that can recognize the totality of an actor’s year across multiple films. — Bill Simmons
In the discussion (6)
Approx. transcript time · 01:02:59Read transcript
- Titanic remains Leonardo DiCaprio’s first apex, while 2006 is treated as a second career summit. — Bill Simmons
- The Revenant is proposed as a third DiCaprio apex. — Bill Simmons
- Blond DiCaprio receives a joking separate apex. — Bill Simmons
- Top Gun: Maverick is favored for Jennifer Connelly because it restored first-call star status. — Bill Simmons
- Blood Diamond is favored over Amistad and Gladiator for the observed Jamon Honsu because it gives him a real arc. — Bill Simmons
- Marathon Man wins the diamond-movie comparison over Diamonds Are Forever and The Hot Rock. — Bill Simmons
Half-Assed Internet Research
DiCaprio family cameos, Dia’s name, Jennifer Connelly’s injury, DiCaprio’s training, and the diamond industry’s objection
In the discussion (6)
Approx. transcript time · 01:01:09Read transcript
- Two women at the airport are reported as Leonardo DiCaprio’s mother and grandmother. — Bill Simmons
- Dia is reported to mean expensive in an adapted Sierra Leone language. — Bill Simmons
- Jennifer Connelly reportedly suffered a serious neck injury during a car chase. — Bill Simmons
- The injury may explain her absence from shots inside the fleeing car, though this remains an inference. — Chris Ryan
- DiCaprio reportedly gained muscle and trained with former Rhodesian soldiers. — Bill Simmons
- The De Beers company is reported as unhappy with the movie. — Bill Simmons
Casting What-Ifs
Russell Crowe was the other reported possibility for Danny Archer; the film chose Leonardo DiCaprio.
In the discussion (2)
Approx. transcript time · 00:58:28Read transcript
- Russell Crowe is the only alternate casting possibility the panel found. — Bill Simmons
- The choice is framed against Crowe’s earlier work with Jennifer Connelly in A Beautiful Mind. — Bill Simmons
What’s Aged the Best?
The explanatory title cards, David Harewood’s villain, child-soldier depiction, diamond smuggling, Leonardo DiCaprio’s 2006 leap, local language, road-movie structure, goat-skin concealment, and lab-grown diamonds
In the discussion (11)
Approx. transcript time · 00:44:37Read transcript
- The opening Sierra Leone title cards efficiently establish civil war and control of diamond fields. — Chris Ryan
- The observed David Harwood villain is immediately hateful yet gains dimension while radicalizing Dia.
- The child-soldier passages show indoctrination through several short scenes without reducing the process to one speech. — Chris Ryan
- The refugee-camp and Western-culpability material make the story more detailed than a short romance-driven version would be. — Chris Ryan
- A diamond hidden in a tooth works as portable currency that immediately funds the next step. — Bill Simmons
- The old light-blue VW bugs provide memorable period texture. — Bill Simmons
- DiCaprio’s 2006 work completes the transition from promising child actor to adult leading man. — Bill Simmons
- The film’s local language and repeated journey through the landscape strengthen the road-movie feeling. — Chris Ryan
- The road structure makes Danny, Maddie, and Solomon’s relationships change through shared travel. — Chris Ryan
- Diamonds concealed inside goat skin are praised as another effective smuggling detail. — Bill Simmons
- Lab-grown diamonds are added as the clearest missed Aged Best answer. — Craig Horlbeck
The Stephen A. Smith Hottest Take Award
Danny’s mountain death and phone call are called the best scene of Leonardo DiCaprio’s career.
In the discussion (2)
Approx. transcript time · 00:40:58Read transcript
- The final mountain scene is chosen over prominent work in The Departed and Shutter Island. — Bill Simmons
- The emotional force comes from Danny returning the diamond, protecting Solomon, and accepting where he will die. — Bill Simmons
Displaying discussions 1 - 12 of 76 in total
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