Leonardo DiCaprio has pushed his name into Oscar conversations with an insidious portrayal of Ernest Burkhart in Killers of the Flower Moon. However, unlike his fans, the 49-year-old would know better than to get carried away based on early reactions, especially in the year when the likes of Cillian Murphy and Robert Downey Jr. have left critics in awe with their own equally engrossing performances.
DiCaprio is considered one of the greatest actors of his generation and yet shares a very tremulous relationship with the most prestigious award in the entertainment industry. He has heard his name from the Oscar stage six times in his career and yet only been called to the center of the stage once – in 2016 for The Revenant. The rest of the five nights have been the subject of plenty of debates, not least because of the merit of the actors who beat DiCaprio to the chase. Accordingly, we have ranked every actor – from worst to best – to pip him for the award.
Forest Whitaker for The Last King of Scotland – 2007
Forest Whitaker taking home the Oscar trophy didn’t just infuriate Leonardo DiCaprio fans, who thought he was brilliant as anti-hero Danny Archer in Blood Diamond, but also Ryan Gosling supporters. The latter delivered the best performance of his career in Half Nelson.
But the same could be said for Whitaker, who gave his all in The Last King of Scotland as Ugandan dictator Idi Amin. The way Whitaker transformed into the real-life dictator to bring different layers of his personality (and a brilliant accent) onto the big screen was certainly admirable. However, underwhelmingly the Black Panther actor didn’t manage to replicate the same level of acting prowess post that movie.
Matthew McConaughey for Dallas Buyers Club – 2014
While DiCaprio made headlines as the womanizing, drug-loving, shady stockbroker in The Wolf of Wall Street and earned an Oscar nomination for Best Actor in a Leading Role, Matthew McConaughey not only gave him a run for his money in the same movie as senior stockbroker Mark Hanna with that iconic chest beating scene but also beat him for the all-important award through his performance as Ron Woodroof in Dallas Buyers Club.
McConaughey showed his dedication to his craft by going to extreme lengths to play a character diagnosed with AIDS and underlined that his acting arsenal includes a lot more things than just his famous Southern charm which many once saw only fit for romantic comedies.
Jamie Foxx for Ray – 2005
Jamie Foxx doesn’t find his name regularly among the greatest actors of his generation but still boasts of having delivered multiple performances that shouldn’t be described as anything else than simply great. In that regard, Ray comes first to everyone’s mind.
To present the extraordinary life of iconic musician Ray Charles, Foxx adopted method acting approach, which included wearing prosthetics to simulate his blindness. His hard work paid off in style and there was little debate concerning his merit when he was named the Oscar winner ahead of DiCaprio (Aviator). In the same year, Foxx also earned an Oscar nomination for Best Performance by an Actor in Supporting Role for Collateral.
Tommy Lee Jones for The Fugitive – 1994
Beating 19-year-old DiCaprio (What’s Eating Gilbert Grape) for Best Actor in a Supporting Role might not seem a very impressive feat on paper, but Tommy Lee Jones’s portrayal of the lead marshal Samuel Gerard in the thriller action opposite Harrison Ford was a big reason behind the success of the movie, as not even the main stars of The Fugitive held a high opinion of the story.
After coming close to the glorious trophy in 1992 for JFK, Jones finally got his flowers for going toe to toe with on-the-run protagonist Richard Kimbel and carrying The Fugitive on his back. The veteran actor didn’t lose his class as he aged and added two more nominations to his name in 2008 and 2013 for In the Valley of Elah and Lincoln respectively.
Joaquin Phoenix for Joker – 2020
If there’s one actor in this list who has played as many different types of characters as DiCaprio and could also claim to be hard done by the Oscar jury on several occasions like the Titanic star, it’s Joaquin Phoenix.
Incidentally, after three Oscar nominations that led to no trophy, the Gladiator actor ended the drought by beating DiCaprio (Once Upon a Time… in Hollywood) by delivering one of the most talked-about individual performances of all time in Joker.
What’s even more impressive about Phoenix is that the gritty and compelling portrayal of Arthur Fleck that held its ground against the legendary Robert De Niro might not even be his best performance to date, as his fans often point toward his captivating work as an unsettled WW II veteran in The Master or an introverted writer yearning for companionship in Her to highlight his true acting potential.
