From Iconic to Unforgettable: Ranking the Last 20 Years of Best Actor Oscar Winners

With the Oscars taking place this Sunday, the nominees for Best Actor are stacked—from Michael B. Jordan’s critically acclaimed performance in “Sinners” to Timothee Chalamet’s A24 hit “Marty Supreme”. Historically, the Best Actor award has gone to actors who have given us iconic performances. These wins give you perspective to reflect on what moments were career-defining for actors, moments that have aged well over time and the preparation given to create an impact. Here’s a ranking of the last 20 years of Best Actor winners ahead of Hollywood’s biggest night. 

20. Matthew McConaughey (2014)

Matthew McConaughey won Best Actor for his role in the 2013 film “Dallas Buyers Club”. The character arc Matthew McConaughey delivers was transformational. He even lost about 40 pounds to really depict the look of someone living with HIV.

19. Brendan Fraser (2023)

Brendan Fraser won Best Actor for his film “The Whale” in 2023. Brendan took an over-10-year break from the industry. He delivered an unforgettable performance that oozed realism with the physical and emotional nuances throughout the film.

18. Adrien Brody (2025)

Adrien Brody won Best Actor for his role in the 2024 film “The Brutalist.” This makes him a two-time Best Actor winner. He previously won for his role in the film “The Pianist”, which was over 20 years ago. But Adrien Brody has a way of showing his range with complex, long narrative films.

17. Philip Seymour Hoffman (2006)

Philip Seymour Hoffman won Best Actor for the film “Capote”. When you’re ambitious, sometimes you’ll let nothing get in your way. He embodies a curious, charming character, yet is not emotionally regulated.

16. Forrest Whitaker (2007)

Forrest Whitaker won Best Actor for his performance in the 2006 film “The Last King of Scotland”. One of five Black actors who have won an Oscar. Forrest Whitaker really showed the duality of being both charismatic and a menace. 

15. Leonardo DiCaprio (2016)

Leonardo DiCaprio won Best Actor for his role in the 2016 film “The Revenant”. Surprisingly, this was DiCaprio’s first Oscar win. He truly embodied the character emotionally, physically and mentally. 

14. Jeff Bridges (2010)

Jeff Bridges won Best Actor for his role in the film “Crazy Heart”. It’s hard to channel loneliness when that’s such an isolating feeling. But he really embodied the character of a person who has struggled and is trying to reclaim his life. 

13. Daniel Day-Lewis (2008)

Daniel Day-Lewis solidified his second Best Actor win with the film “There Will Be Blood”. There’s depth in the films that Daniel Day-Lewis plays. This role completely transformed him into his character.

12. Anthony Hopkins (2020)

Anthony Hopkins is one of the few to win in this category more than once. He won Best Actor for “The Silence of the Lambs” in 1992. And now for his role in the film “The Father”. Anthony Hopkins has the talent not just to play a character but to make you feel and experience it in a unique way.

11. Sean Penn (2009)

Sean Penn took a role that not every actor has the courage to play. He won Best Actor for his role in the 2008 film “Milk”. It was a portrayal of the first openly gay elected official of California. He was able to show in an honest way what that community deals with. And his performance allowed audiences to understand the cause and effects with true emotion.  

10. Casey Affleck (2017)

Sometimes the saddest films are the best performances. Casey Affleck won Best Actor for the 2017 film “Manchester by the Sea”. Playing a character dealing with grief can be a lot, because not much is said. Casey Affleck did a great job of conveying the emotions.

9. Gary Oldman (2018)

Gary Oldman won Best Actor for his film “Darkest Hour”. He played the historical figure, Winston Churchill. He made the movie feel less like an ordinary tale about an important figure. Gary Oldman allowed us to see the man behind the heavy title. 

8. Eddie Redmayne (2015)

Eddie Redmayne won Best Actor for the depiction of Stephen Hawking’s life in the 2014 film, “The Theory of Everything”. To play such a complex role that required both physicality and emotional range was remarkable.

7. Jean Dujardin (2012)

We don’t often see many classic cinema movies nowadays. Jean Dujardin won Best Actor for the film “The Artist”. He did a wonderful job evoking emotion in audiences through humor, love and charm.

6. Cillian Murphy (2024)

Cillian Murphy won Best Actor for the 2023 film, “Oppenheimer”. His performance from the silences to his expression showed control. He didn’t overplay his role in this film to make the character stick.

5. Colin Firth (2010)

Colin Firth won Best Actor for his role in the 2010 film, “The King’s Speech”. His character had a speech impediment. Colin Firth not only played that role accurately. But his performance brought courage, strength and emotional dignity to people who might experience that.

4. Joaquin Phoenix (2019)

Joaquin Phoenix won Best Actor for his role in “Joker”, which came out in 2019. His performance moves beyond just a great portrayal. He really showed what it means to embody a character. 

3. Daniel Day-Lewis (2013)

Actor Daniel Day-Lewis won Best Actor for his film “Lincoln” in 2013. He holds the record for winning three Best Actor awards. 

2. Will Smith (2022)

After many nominations, Will Smith finally won Best Actor in 2022 for his portrayal in the film “King Richard”, about tennis players Venus and Serena Williams and their father. It also goes down as a night in Hollywood history because Will Smith walked onstage and slapped Chris Rock.

1. Rami Malek (2019)

We start this list off with Rami Malek earning the Best Actor Award for the film “Bohemian Rhapsody” in 2019. To play the iconic Freddie Mercury is one thing—but to look almost identical to him is another.

Featured image credit: AP Photo / Mark J. Terrill