Ranking the Decade's Best Supporting Actor Oscar Winners

A pretty solid list all told – the top 3 were actually my choices in those years – easily the highest of any category.

 

10. Jared Leto, Dallas Buyers Club (2013) – I’m not much of a Jared Leto fan, and so even if I do think this is his best performance, it’s still not one that I think really deserved the Oscar. I will say that it deserves some credit as really was the last time a Cis actor could get away with playing a trans character, without major pushback (there was some during his awards run, but the chorus has grown). It is a cliché riddled role, that verges on tragedy porn, and Leto is fine in it – but my opinion has been downgraded over the years, and I didn’t think he should have won at the time.

Who Should Have Won (Of the Nominees): For my money, the best performance nominated was Michael Fassbender in 12 Years a Slave, who is able to make his slave owner a complex character, while maintaining that he is a terrible human being at the same time. This was his first Oscar nomination – and appeared like it was going to beginning of him becoming a perennial nominee – which hasn’t quite happened (too many blockbusters since then) – but he should have won here.

 

9. Mahershala Ali, Green Book (2016) – Ali’s second Oscar is one that he led all season for. Ali is the best thing about Green Book – it is a fine performance, in a problematic movie, but he is witty and charming, and has his big Oscar moments, and is essentially a lead in the supporting category. The Academy clearly loved the film – it won Best Picture of course – but this kind of felt like the Academy pushing back on the criticisms of the film by saying – look, we’re not racist, we gave the black guy an Oscar. I didn’t envy Ali going through the season – and he I wish he hadn’t won this one.

Who Should Have Won (of the Nominees): I thought that Adam Driver in BlackKklansman made what could have been a one dimensional cop character into a complex character, discovering his own identity, through his interactions with the Klan. One of Driver’s best performances.

 

8. Christopher Plummer, Beginners (2011) – You’d have to be a monster to not love the well-over 80 Plummer winning for his charming performance in Beginners – playing a man who finally comes out as gay when his wife dies. The film is perhaps a little too quirky for my liking – by Plummer, a great actor, delivers a great performance – the best thing about the movie, but it’s in a movie that isn’t among my favorites.

Who Should Have Won (of the Nominees): Seriously, maybe Plummer? It wasn’t exactly a banner year for this category in terms of their nominations – they had so many great performances they could have nominated (Brooks in Drive, Pitt in The Tree of Life and many more) and they ignored them all.

 

 

7. Christian Bale, The Fighter (2010) – This performance hits pretty much all the Oscar winning clichés – a major movie star, stripping down for a raw performance, losing weight, playing an addict, and yet still in an inspirational sports movie. And yet, even with all of those clichés, Bale nails the role – he really is terrific in the film, and makes those clichés work so much better than they probably should.

Who Should Have Won (of the Nominees): Bale was a fine choice out of the nominees (again, I kind of think they overlooked a few great performances) – but part of me now wishes that John Hawkes won for Winter’s Bone – a great character actor, and the kind that doesn’t win as much anymore.

 

6. Christoph Waltz, Django Unchained (2012) – I really do love Christoph Waltz in Django Unchained – a funny, charming performance – and yet I think you can argue that he’s using some of the same tricks he used in Inglorious Basterds, which won him his first Oscar, and that both DiCaprio and Jackson are better in this very same movie. Still, a performance I love – but context matters.

What Should Have Won (Of the Nominees): This was one of those strange years where all five nominees had won an Oscar before – so no one was overdue. Still, I think one of the very best performances of the decade was Phillip Seymour Hoffman in The Master – which would end up being their last chance to give a second Oscar to one of the best actors of his generation.

 

5. Sam Rockwell, Three Billboards outside Ebbing, Missouri (2017) – Sam Rockwell has been a talented actor for a long time, and yet he didn’t always get the roles that would lead to Oscars. Here, he plays the racist, violent cop, but with a sensitive side, which is what drove critics of the movie insane, but is what made the performance complex – a horrible person, that Rockwell still makes you like. Personally, I still like Harrelson in the same film more – but I get this one, and Rockwell is terrific.

What Should Have Won (Of the Nominees): I already mentioned Harrelson – and it’s a shame he hasn’t won an Oscar yet – but in particular, I would say Willem Dafoe in The Florida Project – who gives perhaps his most sensitive performance of his great career, and yet again, why has he won an Oscar already?

 

4. Mark Rylance, Bridge of Spies (2015) – I think a lot of people dismissed Spielberg’s Bridge of Spies as an old fashioned film, without realizing that what Spielberg does in this film, old fashioned or not, is something very few directors could do. And Rylance, as a Soviet spy being held by the Americans, is fantastic in the film – funny and wry, somewhat tragic, and emotional – he shows why he is considered a great actor, to movie audiences who may not be familiar with him.

Who Should Have Won (Of the Nominees): Rylance was my choice over the emotional favorite, Sylvester Stallone in Creed, who is great, but come on, he’s been playing that role for 40 years. Rylance was the right one.

 

3. Mahershala Ali, Moonlight (2016) – Ali’s first supporting actor Oscar win for the decade, and by far the more deserving, was in Barry Jenkins’ masterful Moonlight. Ali is only in the first of three segments – a drug dealer, but also a mentor to the main character, whose absence in the later chapters is felt by that character – he leaves a deep impression on the film, and the audience. A great performance, by a great actor, which propelled him to larger stardom.

Who Should Have Won (Of the Nominees): Ali dominated the category for the entire season, and there was a reason – it was a great performance, and nothing else really came close this year.

 

2. J.K. Simmons, Whiplash (2014) – J.K. Simmons performance in Whiplash has already become legendary and iconic – and with good reason. Simmons has always been a great character actor – in all sorts of projects (HBO’s Oz was probably my favorite pre-Whiplash role). This is a great performance as a teacher, who pushes his student to greatness, no matter what the cost- going all the way into abuse, and well beyond. Simmons commands the screen from beginning to end – and dominates. I love the film itself, and Simmons is even better than the film.

Who Should Have Won (of the Nominees): Simmons was head and shoulders above the rest of the nominees – even though it was a very strong field (both Ethan Hawke in Boyhood and Mark Ruffalo in Foxcatcher are excellent) – but Simmons was clearly the right choice.

 

1. Brad Pitt, Once Upon a Time in Hollywood (2019) – Pitt has been a movie star for over two decades now, and one of the most versatile ones out there – fully capable of delivering the type of movie star performances that few can, and also a character actor in other roles. His performance in Once Upon a Time in Hollywood is a combination of those two aspects of his talent. He carries half the film (he probably should have – and could have – been considered a lead). It is a truly great performance, by one of the best actors around.

Who Should Have Won (of the Nominees): This was one of the hardest decisions I ever made – because as great as Pitt is, Joe Pesci in The Irishman is just as good – either winner would have been my favorite of the decade.