Ladies and gentlemen, we’re back! Yes, it’s what I think is actually the most popular series on the site! 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 kicking it off 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 currently rank Daniel Kaluuya for his Academy Award winning turn in Judas and the Black Messiah four years ago? How about Troy Kotsur for CODA three years ago? What of Ke Huy Quan for Everything Everywhere All At Once two years ago? And of course, where does last year’s winner in Robert Downey Jr. place for Oppenheimer fall? Does Kieran Culkin break in at a high position this year for A Real Pain? 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. Daniel Kaluuya – Judas and the Black Messiah
22. Jack Lemmon – Mister Roberts
21. Robert Downey Jr. – Oppenheimer
20. Jack Nicholson – Terms of Endearment
19. Benicio del Toro – Traffic
18. Troy Kotsur– CODA
17. Martin Landau – Ed Wood
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, George Kennedy – Cool Hand Luke, Karl Malden – A Street Car Named Desire, Christopher Plummer – Beginners, Missouri, Mark Rylance – Bridge of Spies, and Christoph Waltz – Django Unchained
Stay tuned for another category early next week!
Fun time ! It’s always fun to revist all the categories
25.Ben Johnson -The Last Picture Show
24.Christopher Plummer -Beginners
23.Haing S.Ngor -The Killing Fields
22.Melvyn Douglas -Hud
21 .Daniel Kaluuya -Judas and The Black Messiah
20.Kieran Culken -A Real PAIN
19.Frank Sinatra -From Here To Eternity
18.Tim Robbins -Mystic River
17.Mahershla Ali -Moonlight
16.Christoph Waltz-Inglorious Basterds
15.Kevin Kline -A Fish Called Wanda
14.Walter Huston -Treasure of The Sierra Madre
13.Javier Bardem -No Country For Old Men
12.Troy Kotsur -CODA
11.Jack Lemmon -Mr .Roberts
10.Heath Ledger -The Dark Knight
9.Robert DeNiro -The Godfather Part Il
8.Edmund Gwenn -Miracle on 34th Street
7.Timothy Hutton -Ordinary People
6.Brad Pitt -Once Upon A Time In Hollywood
5.Alan Arkin -Little Miss Sunshine
4.Burl Ives -The Big Country
3.Joel Grey Cabaret
2.Ke Huy Quan -Everything Everywhere All At Once
1.Christoph Waltz -Django Unchained
HM
Christopher Walken -The Deer Hunter
JK Simmons -Whiplash
Gig Young -They Shoot Horses Don’t They
Robin Williams -Good Will Hunting
Sean Connery -The Untouchables
Benicio Del Toro -Traffic
Peter Ustinov -Spartacus
Excellent job as always!
I would replace Heath Ledger with Burl Ives from The Big Country
Duly noted.
Kevin Spacey for The usual suspects??????
Sam Rockwell for three billboards??? These list are head scratchers Kieran Culkin really ? Dude just played the same character as he did on succession.
Check last year’s list, Rockwell was an honorable mention who fell off in favor of older performances. And I can only go by the film performance, never watched the television show. That being said, he did also win essentially the same prizes for Succession, so he’s clearly doing it well.
The Kieran Culkin win is going to age like milk he didn’t do anything transformative at all he essentially played himself. The person who should have won was Jeremy Strong for The Apprentice he became Roy Cohn in that film. Also the Downey Jr win for Oppenheimer is another one that’s not a amazing win that’s a career win. I love the Oscars but they tend to get it wrong more than they do right. A good example of that is DiCaprio he should have won for Wolf of Wall Street but they give it to him for Revenenet. He was great in it but it was a make-up Oscar the academy these days seems to rarely award the write performance and it’s frustrating.
Noted.
I understand what many are saying aboout Culkin and I don’t really disagree although I haven’t fully watched enough of the show I get it. I would have gone with one of the other nomineesnin the category but his performance has stuck with me in a way most of the acting winners didn’t this year. I took that into account.
Fair enough.
Not a fan of the film or think too much of the performance, so it never was on my list, even years ago.