Three Kings
1999
Co-top favorite. War-as-heist-as-moral-awakening. Style doing argumentative work. Russell never made anything close to it again.
Top Tier
Tinker Tailor Soldier Spy
2011
Co-top favorite. Oldman's best work. Gets bigger the more you know. TTSS standard for institutional betrayal done right.
Top Tier
Confessions of a Dangerous Mind
2002
Clooney's best directorial work. Formally inventive, Rockwell extraordinary. Fun + style + genuine strangeness simultaneously.
Favorite
The Hudsucker Proxy
1994
Coens doing stylized screwball. Form serving feeling not form as performance.
Favorite
Good Will Hunting
1997
Late-20s resonance. Intelligence display that hides rather than shows off.
Favorite
Primer
2004
The other end of intelligence display from GWH. Both work. Smart people solving a mystery at its most ruthless.
Favorite
Almost Famous
2000
Late-20s resonance. Emotional honesty without sentiment. Did its job when it needed to.
Favorite
Sneakers
1992
Smart people in a room figuring things out as pure pleasure. One of the most reliable single predictors of your taste.
Favorite
Quiz Show
1994
Institutional betrayal, moral ambiguity, great dialogue. Redford underrated as a director.
Favorite
O Brother Where Art Thou?
2000
Coens doing myth as comedy. Style in service of something. Great fun without sacrificing intelligence.
Favorite
Hunt for Red October
1990
Smart people in rooms — the submarine as institutional microcosm. Connery at peak watchability.
Favorite
Beautiful Girls
1996
Late-20s resonance. Male arrested development without condescension. Still loved, different reasons now.
Favorite
High Fidelity
2000
Same cluster as Beautiful Girls and Almost Famous. Did its job at the right time.
Favorite
Kicking and Screaming
1995
The thesis statement of the late-20s arrested development cluster. Baumbach's best.
Favorite
JFK
1991
Three hours of men assembling information. Style as argument. Stone using the mystery dopamine loop to make a point.
Favorite
Platoon / Apocalypse Now
1986 / 1979
The Nam entries. Both essential. Apocalypse the more formally ambitious; Platoon the more visceral.
Favorite
Spotlight
2015
All the President's Men's direct descendant. Smart people doing important work without ego. Makes you want to be a journalist.
Favorite
Indiana Jones (Raiders / Last Crusade)
1981 / 1989
Childhood relics. Raiders the better film; Last Crusade the sentimental choice. Pure fun at peak craft efficiency.
Favorite
La La Land
2016
Chazelle's La La Land. Formally inventive, the ending is the Tinker Tailor move applied to a musical. Earns it.
Favorite
Whiplash
2014
Chazelle's thesis: the thing that makes you great is the thing that destroys you. Fletcher unresolved — correct.
Favorite
Babylon
2022
Loved it despite its flaws. Some individually transcendent scenes. Ending a choice — good intention, doesn't land.
Favorite
In Bruges
2008
Genuinely hilarious then genuinely devastating. Farrell's best work. McDonagh's script extraordinary.
Favorite
Banshees of Inisherin
2022
Martin McDonagh again. Grief and stubbornness as tragedy. Farrell and Gleeson both extraordinary.
Favorite
The Nice Guys
2016
The most fun film of the last decade that's also actually good. Shane Black's best. Crowe and Gosling perfect together.
Favorite
Charade
1963
Introduced by your dad young. Teaches that sophistication and fun aren't mutually exclusive. Cary Grant, Audrey Hepburn, Paris.
Favorite
Kiss Kiss Bang Bang
2005
Black workshopping everything that made Nice Guys work. Kilmer extraordinary. The prototype.
Favorite
The Long Goodbye
1973
Altman, Elliott Gould as the most wrong-era Marlowe imaginable. Funny and then quietly devastating. Seen recently.
Favorite
Broadcast News
1987
The Devil speech predicted 21st century culture. Holly Hunter. Smart, funny, genuinely sad. Brooks underrated.
Favorite
Fletch
1985
Chevy Chase at his absolute peak. Genuinely funny mystery. Holds up.
Favorite
Michael Clayton
2007
Belongs on your permanent list. Closest thing to depicting what it's actually like to be a big firm lawyer — the people and vibe, not just the work.
Favorite
Margin Call
2011
Known by heart. Smart people realizing something terrible over one night. The hierarchy, the moral gymnastics — gets the texture right.
Favorite
Inherent Vice
2014
Good but a mess. Talented people who could've been better spent. Long Goodbye DNA. Seen twice.
Favorite