The Top 25 Best Supporting Actor Winners So Far (Updated for 2026)

Two weeks in a row, so you know we’re really back! Continuing a tradition I’ve been doing for years, I’m ranking the newest crop of Academy Award winners. For nearly all of the Oscar categories, you’ll see me list the top 25 recipients of that prize. Sometimes, our newest winner will appear. Other times, they’ll be relegated to the Honorable Mention category. Who knows, maybe one or two won’t even make the cut? It’s a list series that I’ll do each and every single year, in the weeks after the ceremony concludes. So, while this is a fun way to think about the Oscars in the aftermath of the latest telecast, it’s also a beginning for another column here on the site. Of course, definitely show us your own lists as well, in the comments section below. We’re more than keen to know what you think!

This week, we’re continuing on with a big one, the Best Supporting Actor field. My Top 25 Supporting Actor winners are below, but first, a returning bit of commentary. For my money, this is often the most satisfying category of any Oscar night, winner-wise. It’s a place where industry veterans and character actors, as well as sometimes exciting newcomers, can take home the gold. The Academy almost never goes completely off the rails here, and that counts for something. Heath Ledger in The Dark Knight is tops for me, especially since it’s something that Oscar voters had never done before. Other top tier winners of the Supporting Actor prize? Well, for me, they’re Kevin Kline in A Fish Called Wanda, Joe Pesci in Goodfellas, Brad Pitt in Once Upon a Time…in Hollywood, J.K. Simmons in Whiplash, Christoph Waltz in Inglourious Basterds, and Robin Williams in Good Will Hunting. Where do I now rank Daniel Kaluuya for his Academy Award winning turn in Judas and the Black Messiah five years ago? How about Troy Kotsur for CODA four years ago? What of Ke Huy Quan for Everything Everywhere All At Once three years ago? Two years ago, we had Robert Downey Jr. win for Oppenheimer, so where does he now reside? Last year, we introduced Kieran Culkin to the list for his work in A Real Pain. Does Sean Penn break in at a similarly high position this year for One Battle After Another? Read on to find out…

Here are what I consider to be the 25 best winners of the Best Supporting Actor Oscar, to date:

25. Morgan Freeman – Million Dollar Baby
24. Gene Hackman – Unforgiven
23. Jack Lemmon – Mister Roberts
22. Robert Downey Jr. – Oppenheimer
21. Martin Landau – Ed Wood
20. Sean Penn – One Battle After Another
19. Benicio del Toro – Traffic
18. Troy Kotsur– CODA
17. Jack Nicholson – Terms of Endearment
16. Chris Cooper – Adaptation
15. Kieran Culkin – A Real Pain
14. Christian Bale – The Fighter
13. Ke Huy Quan – Everything Everywhere All At Once
12. Michael Caine – Hannah and her Sisters
11. Mahershala Ali – Moonlight
10. Robert De Niro – The Godfather Part II
9. Cuba Gooding Jr. – Jerry Maguire
8. Javier Bardem – No Country for Old Men
7. Brad Pitt – Once Upon a Time…in Hollywood
6. Joe Pesci – Goodfellas
5. Robin Williams – Good Will Hunting
4. Christoph Waltz – Inglourious Basterds
3. J.K. Simmons – Whiplash
2. Kevin Kline – A Fish Called Wanda
1. Heath Ledger – The Dark Knight

Honorable Mention: Louis Gossett Jr. – An Officer and a Gentleman, Daniel Kaluuya – Judas and the Black Messiah, George Kennedy – Cool Hand Luke, Karl Malden – A Street Car Named Desire, Christopher Plummer – Beginners, and Mark Rylance – Bridge of Spies

Stay tuned for another category early next week!