As the Cannes Film Festival launches the beginning of conversations for next awards season, the inevitable discussions of which actors could potentially win their first or second Oscar will begin as well. 23 male actors have won more than one competitive acting Academy Award. Most recently, Anthony Hopkins collected his second Best Actor win in 2020.
The current record for most wins by a male actor is held by Daniel Day-Lewis and Jack Nicholson, with three wins each. But who among those who have won their first Academy Award deserves to win a second? The following actors have delivered excellent, awards-worthy performances both before and after their wins.
Benicio Del Toro
After breakout roles in The Usual Suspects and Fear and Loathing in Las Vegas, Benicio Del Toro swept awards season for his performance as a police officer in one of several interwoven stories about the drug trade in Steven Soderbergh's Traffic.
Del Toro would go on deliver celebrated performances in Alejandro G. Iñáritu's 21 Grams, Soderbergh's Che, and Ben Stiller's Showtime limited series Escape at Dannemora. His performances in the Sicario films have also received critical acclaim and commercial success. Del Toro is long overdue for his next Academy Award nomination, which could come from his upcoming crime film Reptile, a project he is also executive producing.
Gary Oldman
Gary Oldman is known for being a chameleon on screen. The actor rose to prominence in roles such as Count Dracula in the Francis Ford Coppola adaptation of Bram Stoker's Dracula as well as Lee Harvey Oswald in Oliver Stone's JFK. He finally won his first Academy Award for his portrayal of Winston Churchill in the 2017 film Darkest Hour.
Oldman has shown no signs of slowing down since his Oscar win. He went on to portray Herman J. Mankiewicz in David Fincher's film Mank, a behind-the-scenes look at the making of Citizen Kane. Most recently, he starred in the Apple TV+ series Slow Horses and will be reuniting with director Christopher Nolan this year for the highly anticipated Oppenheimer.
Javier Bardem
Javier Bardem became widely popular in American cinema for his villainous turns in Joel Coen and Ethan Coen's No Country for Old Men and in the Sam Mendes-directed James Bond flick Skyfall (he won the 2007 Best Supporting Actor Oscar for the former). By 2007, Bardem also received acclaim for a number of Spanish films including The Sea Inside.
Since No Country for Old Men, Bardem has worked with a number of top film directors, including his Oscar-nominated collaboration with Alejandro G. Iñáritu, Biutiful. He received his fourth Academy Award nomination this past year for his portrayal of Desi Arnaz in Aaron Sorkin's Being the Ricardos, while his wife Penélope Cruz (also overdue for her second Oscar) was nominated in the Best Actress race at the same ceremony.
Brad Pitt
Before Brad Pitt won his first acting Oscar for Quentin Tarantino's Once Upon a Time in Hollywood, he won Best Picture as a producer for Steve McQueen's 12 Years a Slave. Pitt has also been nominated for performances in 12 Monkeys, The Curious Case of Benjamin Button, and Moneyball.
Pitt has been one of Hollywood's biggest movie stars since his brief but memorable role in Thelma & Louise. He has managed to move effortlessly from big budget projects like Mr. and Mrs. Smith to cult classics like Fight Club to prestige dramas like The Tree of Life. He is as prolific a producer as he is an actor. Despite having finally won his acting Oscar only a few years ago, Pitt could enter the race once again with Damien Chazelle's upcoming film Babylon, also starring Margot Robbie.
Leonardo DiCaprio
Like his Titanic co-star Kate Winslet, Leonardo DiCaprio became famous for having never won an Oscar until his 2015 performance as Hugh Glass in Alejandro G. Iñáritu's The Revenant. DiCaprio had collected four acting nominations prior to that win for performances in What's Eating Gilbert Grape, The Aviator, Blood Diamond, and The Wolf of Wall Street.
DiCaprio has worked with some of the greatest living directors, from Martin Scorsese to Quentin Tarantino. For his work with the latter in the 2019 film Once Upon a Time in Hollywood, DiCaprio received an additional acting nomination. Most recently, he led the ensemble cast of Adam McKay's Best Picture-nominated Don't Look Up, but he missed out in the Best Actor race. He will be reuniting with Scorsese on his next film, Killers of the Flower Moon, which is expected to be released this fall.
Joaquin Phoenix
Often considered one of the best actors of his generation, Joaquin Phoenix only won his first Academy Award a couple years ago for the memorable origin story of the iconic Gotham villain in Joker. He had previously been nominated for the epic Gladiator, the biopic Walk the Line, and the cerebral drama The Master.
Those roles alone display the immense range Joaquin Phoenix has as an actor. Although there is an undeniable intensity to his work, Phoenix always finds a way to pivot from what he has already given audiences on screen. Take last year, for instance, when he delivered a beautifully sensitive performance in the critical darling C'mon C'mon. If Phoenix continues to make striking transitions from one performance to the next as he is known to do, winning a second Oscar will not be a surprising occurrence.
Christian Bale
Christian Bale began his career in Steven Spielberg's Empire of the Sun and grew up into an acclaimed and committed actor. Before his notable collaborations with David O. Russell, The Fighter and American Hustle (he won his Oscar for the former), Bale was widely known for his performances as psychopath Patrick Batemen in American Psycho and as Bruce Wayne in Christopher Nolan's iconic Dark Knight trilogy.
The evolution of Bale's filmography is full of surprising transformations. The actor is often known for the extreme lengths he will go to transform himself physically for certain characters, as he did in The Machinist or as Dick Cheney in Vice. In 2022, he will appear in Taika Waititi's Thor: Love and Thunder and will reunite with David O. Russell among an impressive cast in the awards contender Amsterdam.
Morgan Freeman
It's hard to believe that Morgan Freeman did not win Academy Awards for his performances in The Shawshank Redemption and Driving Miss Daisy. In fairness, he was competing with the likes of Tom Hanks and Daniel Day-Lewis. Freeman would not win Best Supporting Actor until a decade after Shawshank, when he reunited with director/actor Clint Eastwood for Million Dollar Baby.
Freeman's performances are varied, yet consistent, and he has delivered a significant amount of under-recognized work in films like Glory, Amistad, and Se7en. He has also managed to maintain a stellar dramatic resume while dabbling in big budget mainstream films like Bruce Almighty and The Dark Knight trilogy. For all that Freeman has given to cinema across various genres, he is certainly overdue for a lead acting Oscar.
Al Pacino
Robert De Niro has two acting Oscars. So does Dustin Hoffman. But Al Pacino, who hails from the same generation and who helped redefine an era of film acting, only has his Best Actor Oscar for Scent of a Woman. That was his eighth nomination in a notorious losing streak that included losses for The Godfather, Serpico, and Dog Day Afternoon.
Pacino has worked steadily since that first Oscar. He won two Emmy awards for his portrayals of Roy Cohn and Jack Kevorkian in the HBO dramas Angels in America and You Don't Know Jack, and he played Shylock in The Merchant of Venice on the Broadway stage. Most recently, Pacino reminded moviegoing audiences just how special an actor he is when he stepped into Jimmy Hoffa's shoes in Martin Scorsese's sprawling epic, The Irishman.
Samuel L. Jackson
Samuel L. Jackson's Academy Award win comes with an asterisk. He was awarded the Governors Award for lifetime achievement at the most recent 2022 ceremony. He has never won a competitive Oscar, not even for his pitch-perfect performance in Quentin Tarantino's Pulp Fiction, although he was nominated.
Jackson has brought gravitas to every role he has played, large or small, prestige or commercial. His resume is extensive and impressive; he is, after all, the highest grossing actor of all time. From the Marvel Cinematic Universe to the Star Wars galaxy, from his iconic line deliveries in films like Snakes on a Plane to his unforgettable collaborations with Spike Lee, Samuel L. Jackson has made an indelible impression on American cinema and deserves to be properly acknowledged for his decades of hard work.