6 Best Oscar Best Actor Winners of the 2000s

By Vlad Zakh · June 19, 2026

The Academy Award for Best Actor in the 2000s crowned a decade of raw, commanding, and deeply human leading performances. In Training Day (2001): A rookie cop’s first day with a corrupt veteran detective spirals into a dangerous test of loyalty and morality. Just as strong is Mystic River (2003): Three childhood friends reunite as adults when a shocking murder reopens the trauma of their shared past.

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

A gay rights activist becomes one of the first openly gay elected officials in the United States, only to be assassinated.

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 writing 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 blind musical prodigy overcomes poverty and addiction to become a beloved American icon.

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 when a shocking murder reopens the trauma of their shared past.

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 veteran detective spirals into a dangerous test of loyalty and morality.

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, built to fix a specific annoyance: most recommendation sites are just algorithm-driven noise. Our lists are researched and organized by who's in a film, where it's from, and the mood you're actually 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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