The roaring 2020s have brought a plethora of challenges to the film industry. A pandemic, multiple strikes, and more have all shaken Hollywood to the core. However, not all of the changes that have come with this decade are negative. For example, the Oscars awards body has steadily diversified its voting membership each year. It has come to the point where it’s starting to feel like any contender from anywhere in the world has a serious shot at receiving that coveted little gold statue. These shifting tides are visible in all major categories since the 2020 Academy Awards, including Best Supporting Actor.

In the best supporting actor category, the winners have been more varied than ever before. A couple of actors have been household names for years, while others achieved their star-making moments at their respective ceremonies. All that being said, here is my ranking of the five Best Supporting Actor winners of the 2020s so far: 

5. Brad Pitt in Once Upon A Time… In Hollywood (2019)

Image via Entertainment Weekly; Credit to Rachel Luna/Getty Images

This may be a controversial take, but Brad Pitt is pretty spellbinding in Quentin Tarantino’s latest feature. Since the film’s Cannes premiere and subsequent theatrical release, his role as the enigmatic stunt man Cliff Booth has been a key takeaway with the film as a whole; which is saying something in a Tarantino movie that also features Leonardo DiCaprio and Margot Robbie. This is the ultimate movie star role, taken by one of our preeminent movie stars in a way that is exciting to watch but not surprising to see. While his character has mystery and personality, it can tend to be a bit of a one-note performance at times, carried by an amazing (as always) script by the writer-director extraordinaire. 

4. Troy Kotsur in CODA (2021)

Image Credit to Gilbert Flores/Variety

Although this win is on the lower end of the list, Troy Kotsur’s performance in CODA is not bad by any means. His earnest turn as Frank Rossi drives the film’s sometimes humorous and sometimes emotional core. Without him, the film would not have gone on to have the Oscar success that it did. In particular, his scene with Emilia Jones in the back of the family’s pickup truck where she sings to him is one of the most emotionally effective scenes from any movie that year. There is depth to Frank that makes him a beacon of light in an otherwise uninspired experience. None of the other supporting characters have the same complexity and humanity that Troy imbues throughout the film. 

Quality of the film aside, it cannot be understated how important this Oscar victory is. He became the first deaf man to win an acting award. Troy’s Academy Award signifies the continued diversification of talent and recognition that the Oscars so desperately needs.

3. Robert Downey Jr in Oppenheimer (2023)

Image Credit to Esquire and Jeff Kravitz

It was clear early in the 2024 Academy Awards season that Robert Downey Jr was on a one-way trip to Oscars Gold. Although the performance itself is divisive, there’s no denying that the role of Lewis Strauss was a stark departure from what audiences learned to expect. Strauss provided RDJ with an incredible opportunity to showcase his range as an actor and solidify his star power in the anoles of film history. 

Given the immense size of the cast and the scale of the story, RDJ makes the most of his limited screen time. He successfully hides the charms that have made him a household name and becomes (nearly) unrecognizable. For better or worse, this win feels like recognition of a long-standing, stellar career. 

2. Ke Huy Quan in Everything Everywhere All At Once (2022)

Image Credit to Mike Coppola / Staff/Getty Images

Few celebrities have comeback stories as extraordinary as Ke Huy Quan. The role of Waymond could never be played by anyone else, and his performance adds so much heart and dimension to the Best Picture-winning film. Not only are his emotional moments top-notch, but he also dishes out incredible fight choreography and physical comedy. It had been thirty years since his last major film role, so it was staggering to see him effectively convey all of these abilities in this role. 

He excels as a loveable oaf of a husband/father at the beginning of the film with impeccable chemistry with Michelle Yeoh and Stephanie Hsu. In equal measure, he succeeds as the more mature sophisticated version that appears in the famous “In the Mood for Love” sequence, explaining how “…in another life, I would have really liked just doing laundry and taxes with you.”  With those two versions and all others in between, Ke Huy Quan shows that time did not diminish his award-worthy talent. 

1. Daniel Kaluuya in Judas and the Black Messiah (2021)

Image Credit to Chris Pizzello-Pool/Getty Images

A new superstar was immortalized when Daniel Kaluuya won for his role as Fred Hampton. There is no film without Kaluuya’s titanic performance. He lights the screen on fire with his electricity. It’s daunting to portray a famous figure, treading the lines between impersonation and interpretation. This rendition of Fred Hampton is the perfect combination of both sensibilities. Although a global pandemic plagued the 2021 Oscar ceremony, Daniel Kaluuya would have still been a force to be reckoned with in a normal awards season. For anyone who may have missed this film when it came out, I highly recommend checking out any one of the speech scenes. There’s no better explanation for why Kaluuya is number one than that. 

List Courtesy of Gabe Lillianthal

Feature Image from ‘Judas and the Black Messiah;’ Credit to Warner Bros via The New York Times