6 Best Oscar Best Actor Winners of the 2000s

By Vlad Zakh · June 19, 2026

The 2000s Best Actor winners were raw, commanding and deeply human. Jeff Bridges won for Crazy Heart, Sean Penn for Milk, Philip Seymour Hoffman for Capote and Jamie Foxx for Ray. Sean Penn again in Mystic River and Denzel Washington in Training Day round out the six.

Crazy Heart (2009)

TMDB ★ 7.1

A washed-up, alcoholic country singer finds unexpected hope through a young journalist and her son.

Directed by Scott Cooper · 1h 52m · Rated R

Where to watch

Rent or buy: Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Milk (2008)

IMDb ★ 7.5 RT 93% Metacritic 83

Harvey Milk's rise as America's first openly gay elected official, and the assassination that ended it.

Directed by Gus Van Sant · 2h 08m · Rated R

Won 2 Oscars66 wins & 146 nominations

Where to watch

Stream: History Vault · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Capote (2005)

TMDB ★ 7.3

A celebrated author's obsessive research into a small-town murder consumes him while he writes his masterpiece.

Directed by Bennett Miller · 1h 54m · Rated R

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Ray (2004)

TMDB ★ 7.6

A note-perfect Ray Charles biopic anchored entirely by Jamie Foxx's performance.

Directed by Taylor Hackford · 2h 32m · Rated PG-13

Where to watch

Stream: Starz Apple TV channel · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Mystic River (2003)

IMDb ★ 7.9 RT 89% Metacritic 84

Three childhood friends reunite as adults after one of their daughters is murdered.

Directed by Clint Eastwood · 2h 18m · Rated R

Won 2 Oscars57 wins & 144 nominations

Where to watch

Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Training Day (2001)

IMDb ★ 7.8 RT 74% Metacritic 71

A rookie cop's first day with a corrupt narcotics detective becomes a single, brutal test of loyalty.

Directed by Antoine Fuqua · 2h 02m · Rated R

Won 1 Oscar18 wins & 23 nominations

Where to watch

Stream: fuboTV, MGM+ Amazon Channel, Philo, MGM Plus Roku Premium Channel, MGM Plus, TNT · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Streaming availability data from JustWatch, via TMDB. Availability changes often, so check the service before you plan a movie night.

Vlad Zakh

Founder, Movieix

Founder of Movieix. He started the site because most recommendation pages felt like noise. Here, lists are sorted by who's in the film, where it's from and what mood you're in tonight.

6 Best Oscar Best Actor Winners of the 2000s

Crazy Heart (2009)

Milk (2008)

Capote (2005)

Ray (2004)

Mystic River (2003)

Training Day (2001)

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