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Film credit

Matt Dillon

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Episodes featuring their films
4
Movies in this archive
4

Rewatchables episodes featuring Matt Dillon’s films

Wild Things

1998 film

Bill Simmons · Van Lathan · Mallory Rubin

Aired February 3, 2026

Crash

2004 film

Bill Simmons · Van Lathan · Joanna Robinson

Aired February 25, 2025

Singles

1992 film

Bill Simmons · Chris Ryan · Van Lathan

Aired September 13, 2022

Displaying all 4 episodes

Mentioned in discussions

In the discussion (5)
Approx. transcript time · 01:40:50Read transcript
  • Matt Dillon is selected for being the viewing’s funniest surprise — Chris Ryan
  • Ben Stiller is selected for the long comedy-star run the film launched — Chris Ryan
  • Cameron Diaz is selected because the title, poster, and cultural impact center her
  • The contemporary 1998 winner is framed as Diaz while Dillon is the retrospective winner
  • The Farrelly brothers are credited with the film’s construction and immediate promise — Craig Horlbeck
In the discussion (7)
Approx. transcript time · 01:23:26Read transcript
Bad Boys The Rewatchables
In the discussion (2)
Approx. transcript time · 00:12:34Read transcript
  • Matt Dillon reportedly wanted the part but was judged too famous; his version would be more conventional or popcorn-oriented, and Cruise would also change the movie. — Bill Simmons
  • Rosenthal reportedly rejected Dillon because My Bodyguard had covered similar ground and his movie-star recognition could prevent viewers seeing only Mick. — Bill Simmons
The Godfather Part III

Casting What-Ifs

Alec Baldwin as Vincent; Robert De Niro as Vincent; Frank Sinatra as Don Altobello; Joe Spinell as Willie Cicci

In the discussion (7)
Approx. transcript time · 01:01:20Read transcript
  • Alec Baldwin as Vincent seems true and may have been his before he dropped out, part of a strange late-80s run of decisions. — Bill Simmons
  • Nicolas Cage, a family member, could have been good.
  • From internet lists, Tom Cruise, Matt Dillon and Val Kilmer are not believed; Charlie Sheen maybe; Vincent Spano makes sense; Billy Zane is listed; a Luke Perry audition is doubted; where they landed was right. — Bill Simmons
  • De Niro wanting to play Vincent, with Pacino aged up, seems true; Coppola did think about it. — Bill Simmons
  • Sinatra for Altobello is carried into the what-ifs alongside the names mentioned for Vincent. — Bill Simmons
  • The actor who played Willie Cicci (transcribed "Joe Spinelli") was supposed to work for Zasa but died before the movie, so the character was written out. — Bill Simmons
  • Paramount approached Sly Stallone, Scorsese, Cimino and Warren Beatty over the years; in the early 80s Stallone was to write and direct with John Travolta, and there is an internet rumor that Eisner took a run at the script.
The Holiday The Rewatchables
The Holiday

Recasting Couch

Jason Segel as Miles; Emilia Clarke as Iris; Kate Hudson as Amanda; Colin Firth as Graham, though no one is as hot as Jude Law; earlier, Matt Dillon or Jason Segel for Jack Black's role

In the discussion (4)
Approx. transcript time · 00:58:52Read transcript
  • Jason Segel is nominated for the Miles role and wins over a skeptic on the strength of his Dracula puppet opera; Emilia Clarke, Daenerys Targaryen, would be fantastic as Iris.
  • Kate Hudson could have been Cameron Diaz, contemporaneously accurate with the L.A.-ness and rom-com chops and maybe better at the sappiness, though that would mean McConaughey in Jude Law's job, which needs a British accent; Wedding Planner McConaughey is still loved.
  • Eddie Redmayne is rejected as not hot enough and too direct; Colin Firth could do it with Hugh Grant-style aloofness, having done the messed-up Love Actually plot where he is helpless and says I love you; but nobody is as hot, and the movie does not work without Jude Law, who brings it all together.
  • While still on casting, one host had an idea to recast Jack Black: Matt Dillon, good looking, slightly older and funny in Something About Mary and Beautiful Girls, though always a jerk and not plausibly musical; or Jason Segel, who sings, likes to be dramatic, and whose Knocked Up and Sarah Marshall characters would fit the movie.
In the discussion (12)
Approx. transcript time · 00:33:32Read transcript
  • The soundtrack: generic, predictable songs that are perfectly executed and make sense with the plot, not a Dazed and Confused soundtrack but what guys going to Vegas then would be listening to; the music under the blackjack scene with the numbers is smart, and the T.I. song Live Your Life was huge and still is.
  • A tangent on which songs from this century have joined the wedding mix: Heya (as transcribed) by Outkast, probably the T.I. song, Bruno Mars, Adele, and 1901 by Phoenix heard at 18 weddings, pitched as a Ringer piece.
  • Todd Phillips' taste for hard rock, the Danzig song at the start and the Metallica in Old School; the Dan Band has also aged well, with future generations asking why they never played the Super Bowl halftime show, and the 'just the tip' setup turning inappropriate fast.
  • Rachel Harris as the girlfriend from hell is an incredible character, every stereotype put on steroids to make her the worst character of all time; the 'you fucked a waiter on a cruise' bit and Galifianakis's 'what did she say' after Helms walks away are singled out.
  • The elevator scene with Todd Phillips' cameo; his habit of going down on a woman in his own movies is his version of Hitchcock walking across the frame.
  • Alan reading the letter on the roof with 'that's why they call it Sin City'; the subtle cut where he is finishing a description of the Ted Danson and Magnum PI movie as they head to Heather Graham's hotel; and the 'it's not illegal, it's frowned upon, like masturbating on an airplane' exchange ending in 'thanks a lot, Bin Laden', the hardest one host laughed.
  • 'Alan, you're the man' answered with 'you are too, Phil' shows he has no idea how to be one of the guys; his aping of Phil throughout is well done; the two made-up songs are enjoyed, and Ed Helms' piano song while they wait for the tiger to fall asleep was apparently ad-libbed.
  • Old-school, last-decade Vegas; every Alan line, especially 'this isn't the real Caesar's Palace, is it? Did Caesar live here?', and the pitch-perfect reaction of the woman at the desk.
  • How high Alan ranks in the pantheon of comedy characters: the criterion is someone who was not the star but stole the movie, so Frank the Tank, John Candy in Stripes, Bill Murray and Ted Knight in Caddyshack, Rick Moranis in Ghostbusters, Matt Dillon and Chris Elliott in There's Something About Mary, Michael Keaton in Night Shift, Steve Carell and Paul Rudd in Anchorman, McLovin, the Wedding Crashers character as the backfire case and Melissa McCarthy in Bridesmaids as the perfect example.
  • Galifianakis belongs in that conversation as the breakout; John Candy in Stripes was like that for a host who knew him only as Ox and never watched SCTV; Galifianakis is named the big winner.
  • The movie stood up in total for a host without as much of a rewatchable relationship to it; the actual plot of what happened to them is well done, with Jade, Mr. Chow and the roof payoff; the brevity, about an hour thirty-five with no wasted section, makes it the last comedy before the two-hour-ten Apatow era.
  • The DVD's deleted scenes were anticipated; the end credit sequence has held up as a convention, 'they pretty much invented Marvel right there', though another host had it for what aged worst.
In the discussion (9)
Approx. transcript time · 00:57:35Read transcript
  • Asked whether this is the Apex Mountain of rom-coms, the first answers are a flat no, twice, before the hosts call it essential to the genre, top five for one, the first to twist the rom-com gimmick and the last place the genre could go; whether it is the apex before the genre went downhill draws only a maybe, a case could be made, and a flat not convinced.
  • The twist and the respect for the rom-com form are liked, since it gets the impulse to see people together before twisting it; Notting Hill in 1999 is raised as a further meta-commentary that is really Julia Roberts' life, with her playing a bad person there too.
  • Rupert Everett is a 100 percent yes, an iconic performance and the breakout element the movie needed alongside the comeback star and the second star; he went on to the Madonna movie, which has not aged well, had James Bond talk about whether he could be the first gay Bond, and this remains his most mainstream and most fun performance beside period pieces like Madness of King George and The Importance of Being Earnest.
  • Cameron Diaz is not at her apex here, though she is really good; her apex is There's Something About Mary, a massive movie that arguably deserved an Oscar nomination and made her a gigantic star, after which she dated Matt Dillon and entered the Us Weekly stream.
  • Her dating history is called rough by one host because it never worked out, and impressive by another: Justin Timberlake, the baseball player known as A Rod, a broken nose surfing; the JT age gap is compared to Sandra Bullock and Ryan Gosling.
  • Julia Roberts is a yes: Pretty Woman blew her up, but this movie re-established her as the most bankable, A plus list actress, set up the next five years and led to her Oscar, so it righted the ship; one voice finds that reasonable, and Ocean's Eleven is floated for her astonishing but not lead role.
  • Chicago as an Apex Mountain is rejected as insulting; Dermot Mulroney is a yes for sure, since it never got better, or worse, for him.
  • An early aside calls 1997 and this film arguably the apex of rom-coms, the top of the crescendo, after which the genre went off a cliff a little.
  • Before the categories, one host previews that Cameron Diaz's Apex Mountain is There's Something About Mary, a role nobody else could have played as likable, funny and slapstick.
In the discussion (3)
Approx. transcript time · 01:00:46Read transcript
  • With only two choices, Keanu Reeves or Patrick Swayze, the answer is Bodhi, repeated several times because he put his fingerprints on everybody and Utah lets him go; after clarifying the question is about the actor, the answer stays Swayze. The repeated affirmations cannot be shown to come from different hosts, so only one ballot is counted.
  • Utah let him go at the end despite responsibility for 12 deaths, or 20 deaths and billions in damage.
  • A host adds that Swayze won the movie and was putting up wins year after year, winning Roadhouse, Ghost going away, Dirty Dancing and Young Blood with Rob Lowe; The Outsiders is the one he did not win, Matt Dillon did.
Podcast choices
Speaker not identified
Patrick Swayze
In the discussion (10)
Approx. transcript time · 00:21:08Read transcript
  • JT Walsh gets an 'Apex for me for sure' and a second yes calling it his most infamous role, prompting a joke about how seriously the question was taken.
  • Aaron Sorkin is close but not the apex, a nice view but not the top; the first season of The West Wing and The Social Network are his apex, this film is likened to his 63-point Michael Jordan game with not a bad scene in it, and Moneyball is set aside because he rewrote somebody else's script.
  • Kevin Pollack is a no because of The Usual Suspects, which another agrees with.
  • Kevin Bacon is a no from one panelist, who calls him great and underrated here but notes how many films he has made, with The River Wild mentioned; another says no too, theorizing his bad haircut was deliberate so he would not distract from Cruise, like Kiefer's haircut, and puts his apex at Footloose, also liking him in Mystic River.
  • A third panelist disagrees with both and says this is Bacon's apex: not a meaty part but memorable, likable, with a dash of unintentional comedy, and hard to imagine anyone from that era, such as Matt Dillon, playing it without competing with Cruise.
  • Bacon was taking smaller parts in bigger movies then, as in JFK; though he is on the prosecuting side backing Jessup, he has some morality, saying he does not think the guys deserve jail but does not make that call; after an aside that his leaving the pickup game is unforgivable, a 'yes' for him is restated, possibly by the same panelist.
  • Wolfgang Bodesen (as transcribed) is a yes: 'that's the Apex for Wolfgang. I wish him well.'
  • Jack Nicholson's career overall draws four 'No' answers; then 'Late Jack Nicholson. Yes.' is offered, with one voice naming As Good as It Gets, and challenged over The Departed the late-career yes holds, because the Departed performance with its accent as a Whitey Bulger figure is called out of control and the weak link of that film.
  • Tom Cruise gets two yeses, with this chosen over Cocktail and a 'this or The Firm' aside; no one else in 30 years could bring this mix of unintentional comedy, good acting, sarcasm and bravado, Leo DiCaprio could not, though Matt Damon ten years later might have.
  • A TV version is planned for next year with Alec Baldwin, who is called amazing, but Caffey has not been cast; James Franco was rumored, a terrible idea, since the part needs an airhead who is really smart, a lawyer who plays softball, attractive but not a romantic lead; Demi Moore is left off the list as the nadir of her career.
Displaying all 12 discussions

Films in the archive