No. 1
The Talented Mr. Ripley 1999
No. 1 - the outlier in his career, playing insecurity instead of overconfidence under a full transformation opposite Jude Law and Philip Seymour Hoffman.
The Big Picture · Top Five · Interview
Top Five Matt Damon Movies and James Mangold on ‘Ford v Ferrari’ | The Big Picture
November 15, 2019/ 119 min/ Sean Fennessey · Amanda Dobbins · Chris Ryan
Amanda Dobbins and Chris Ryan each count down their five best Matt Damon performances, then Sean sits down with James Mangold to talk 'Ford v Ferrari,' the 24-hour Le Mans race, and why he'd rather build a world than wear a superhero costume.
18 films across 3 segments.
AI-generated This episode was transcribed and analyzed with AI models. The matches aren't perfect — expect the occasional misheard title or a link to the wrong film.
Amanda Dobbins's Top 5revealed No. 5 up to No. 1
No. 2
Good Will Hunting 1997
No. 2 - the performance every later role gets measured against: prick-headedness, then the big cathartic release.
No. 3
The Martian 2015
No. 3 - his broadest, most everyman turn, and, as Amanda puts it, a $100 million vlog about not getting addicted to opiates on Mars.
No. 4
The Bourne Identity 2002
No. 4 - the movie that reset his career after 'All the Pretty Horses' and set up the next 20 years. Also, per Amanda, one of his hottest scenes.
No. 5
The Departed 2006
No. 5 - more charisma than usual, a duplicitous Boston cop mirrored against Leonardo DiCaprio's wide-open undercover mole.
Chris Ryan's Top 5revealed No. 5 up to No. 1
No. 1
Rounders 1998
No. 1 - the Chucky to Edward Norton's Will Hunting, and as close to Jimmy Stewart as Damon ever gets. Chris says there's not a false note in it.
No. 2
Good Will Hunting 1997
No. 2 - same pick as Amanda's, for the same reason: the role everything after it answers to.
No. 3
The Departed 2006
No. 3 - Chris calls it Damon's best pure performance, closed-off and slimy in a way that requires real self-awareness to play.
No. 4
Contagion 2011
No. 4 - one of eight collaborations with Steven Soderbergh; his reaction to Gwyneth Paltrow's death is some of the best acting he's done.
No. 5
Courage Under Fire 1996
No. 5 - a physical-transformation role as a heroin-addicted medic, in a scene where Denzel Washington cedes the moment to him.
In conversation
James Mangold on
Ford v Ferrari 2019
His new film. The red folder scene was his idea, a way to make Carroll Shelby's pitch to Henry Ford II visual. He built the climax around a sustained, nearly 50-minute cut of the 24-hour Le Mans race, telling the crew they were shooting 'Saving Private Ryan in reverse.'
James Mangold on
Logan 2017
His version of an IP movie, without a supervillain or a costume Wolverine would ever actually wear, structured like a 'Kramer vs. Kramer' character piece instead of a comic-book plot.
James Mangold on
Walk the Line 2005
About a man who can only be with the woman he loves for 30 minutes at a time onstage. Joaquin Phoenix's singing voice didn't click into Johnny Cash's register until ten days before they left for Memphis.
James Mangold on
Girl, Interrupted 1999
Cited as an earlier example of the kind of adult drama he keeps returning to.
James Mangold on
Heavy 1995
His directorial debut, made deliberately against the '90s indie-cool grain, inspired by 'The Last Picture Show.'
James Mangold on
Cop Land 1997
Miramax expected something Tarantino-adjacent; he made an earnest, Western-structured drama instead.
James Mangold on
The Wolverine 2013
His closest attempt at a studio IP picture, conceived as a Tokyo noir. He came away unsatisfied and told the studio he wouldn't do another one the same way.
James Mangold on
Ad Astra 2019
James Gray's film, his pick for the last great thing he's seen. It's patient and unhurried, and it doesn't let the audience off easy.
Also mentioned raised along the way
More from the Matt Damon lists DogmaTrue GritMargaretOcean's ElevenOcean's TwelveOcean's ThirteenThe Informant!Behind the CandelabraSyrianaSaving Private RyanSchool TiesDownsizingPromised LandWe Bought a ZooThe Great WallSuburbiconElysiumGreen ZoneAll the Pretty HorsesThe MajesticGerryInterstellarThor: RagnarokDeadpool 2UnsaneEurotripThe Brothers GrimmThe Monuments MenJay and Silent Bob RebootManchester by the SeaInvictus
Mangold's touchstones Sweet Smell of SuccessThe Man in the White SuitThe LadykillersWhisky Galore!Kramer vs. Kramer
Not films filtered out: TV, games, ads
TV Jimmy Kimmel Live!30 RockThe Fresh Prince of Bel-AirThe Defenders
Podcasts The Bill Simmons PodcastThe Moment with Brian Koppelman