The studio wanted Matt Damon or Sean Penn for the narrator while Fincher wanted Norton; Norton was also up for The Talented Mr. Ripley, Man on the Moon and Runaway Jury in a casting merry-go-round. — Bill Simmons
An alternate universe where Damon does Fight Club and Norton does The Talented Mr. Ripley is fun to imagine, though Damon's Ripley is one of his best roles. — Bill Simmons
Norton and Damon competed for The Rainmaker, Coppola steered Norton to American History X, and Damon has said he was devastated to miss Primal Fear; Scent of a Woman went to Chris O'Donnell. — Chris Ryan
Damon brings relatability and Norton a cerebral quality; Damon could have played either part, Pitt only Tyler, and Norton not Tyler. — Chris Ryan
Leo was a little young post-Titanic but this would have been his dream part a few years later; Pitt's casting works because he is who guys daydreamed of being. — Chris Ryan
Crowe was about to go on his Gladiator-Insider-Beautiful Mind run and would have crushed the part with an Aussie hooligan authenticity, though Pitt is still preferred. — Bill Simmons
Fincher's first choice for Marla was Janine Garofalo; she reportedly accepted, then was dropped as not right for the role at Norton's urging, framed as the birth of the behind-the-scenes Norton monster. — Bill Simmons
Per Variety, Sarah Michelle Geller was sought but was doing Buffy; the studio wanted Reese Witherspoon, whom Fincher thought too young, and then Courtney Love, who was dating Norton, before landing on Bonham Carter. — Bill Simmons
Marla is said to have Courtney Love meets Joan Crawford energy, leading to a tangent about loving the band's 90s songs. — Bill Simmons
Fincher wanted Radiohead to score the film; it would have been eerier and more somber than the Dust Brothers' electronic score, not necessarily better, though the movie needs the Dust Brothers' energy. — Chris Ryan
The pick is narrowed from the opening cocktail party to Josh Hamilton and Olivia Diaba on the balcony, where she says she is going to Prague and he claims he has been to Prague; it introduces their relationship. — Bill Simmons
Prague was a mythical post-Berlin-Wall destination heard about on campuses, requiring a Fodor's book, a visa and travelers checks, so "going to Prague" became a thing in itself. — Andy Greenwald
A college roommate came back from a Prague junior year abroad judging everyone; skipping a semester abroad is a regret; the movie was seen on Thayer Street in Providence before the first Starbucks there. — Bill Simmons
The graduation party is up there with the wedding in The Godfather for getting to know every character, Skippy, Max and Otis. — Chris Ryan
The "You never even been to Prague" exchange riffs on the stop-shaving-your-armpits, read-The-Unbearable-Lightness-of-Being version of Prague.
The book club scene, added because Eric Stoltz had to be shoehorned in with ad-libbed scenes, has about seven laugh-out-loud lines about All the Pretty Horses.
Hollywood roller coaster: Stoltz was removed from Back to the Future, and ten years later this movie could not get money without him. — Andy Greenwald
Further nominations: Grover confronting Max about sleeping with Miami, with Chet sneaking back in; Skippy confronting Max; and Grover and Chet at the bar, where Chet saw it as a postponement of his life until realizing it was his life. — Bill Simmons
The final airport scene is spectacular: Grover's roughly three-minute monologue on a whim to go to Prague, with the camera on him.
Hamilton's airport performance echoes Dustin Hoffman banging on the church at the end of The Graduate. — Andy Greenwald
If asked at the end of 1995 which five young actors to bet on, Chris O'Donnell, Damon and Omar Epps would have been on the list along with Hamilton; the part could easily have been a Matt Damon part, but Hamilton is perfect in it. — Bill Simmons
Hamilton suffers on Google from the Texas Rangers ballplayer of the same name and is part of the 90s New York theater crew with Billy Crudeup, Ethan Hawke and Robert Sean Leonard. — Andy Greenwald
Jessica Hacked, who was on Friends as the lesbian lover of Ross's ex-wife, is great as the stewardess in the airport scene. — Bill Simmons
The flashbacks work, perhaps as the story Grover is writing, and the ending goes straight into the Fridi Johnson song Bad Reputation, a needle drop that hits like a bomb.
The last line, "let's pretend we're an old couple," happens before everything chronologically, and they do not actually kiss. — Andy Greenwald
The airport scene is one pick, with a special shout-out to the entire graduation party as a meet-everyone-at-a-gathering opening.
Every scene is equally rewatchable because the tone is so consistent, but the shout-out goes to the scene where he would rather be bow hunting.
Dunn has been in a lot of stuff: Mississippi Burning, Hot Shots, 1492, Chaplin, Beethoven's 2nd, Little Big League, Nixon, Chain Reaction, Picture Perfect, Godzilla, Stir of Echoes, Snake Eyes, I Heart Huckabees, a bunch of Transformers movies, Warrior, and five years being really funny on Veep; he is hall-of-fame that guy, the award could be called the Kevin Dunn award, and there were no other candidates.
Kate Winslet had to do a screen test, watchable online, opposite Jeremy Sisto, Elton from Clueless, who auditioned but probably was not in contention; the major name in contention for Jack Dawson was Matthew McConaughey.
Stephen Dorff is the verified one: a New York Daily News piece headlined 'actor is thankful he didn't get Titanic role' has the Blade co-star saying he wanted a career like Johnny Depp, Sean Penn and Jack Nicholson and an Oscar, which Titanic would have made impossible, and that Leo will always be the guy on the boat.
One host disagrees that Leo is the guy on the boat, since he has been in so many hits and everyone has a favorite Leo, whereas Matt Damon and Ben Affleck are more locked into their 90s work; Sofia Coppola is said to have made Somewhere with Dorff because he never blew up, and Titanic will be in the first line of DiCaprio's obituary, and of Billy Zane's.
Billy Zane has not done much anyone has heard of since, though he has been in three times as many films as Kate Winslet.
Chris O'Donnell, named on Wikipedia for Jack, would have been a great and adorable Jack given his Batman movies and a season-two television arc, but could not have taken the film past a billion dollars; Leo is singular and the chemistry is enduring, though he seems strikingly innocent and little in it.
Rob Lowe was in the mix for Cal and is a great asshole, as in St. Elmo's Fire; pre-West Wing he might not have pulled viewers out of the film, though one host says he would have a little, and the leads mostly had blank or clean reputations at the time, which the hosts think mattered.
