By Ryan O’Toole
Ariana Debose has won the Golden Globe, Critics Choice, BAFTA, and SAG awards for Best Supporting Actress for her role as Anita in Steven Spielberg’s 2021 adaptation of “West Side Story.” She is now the odds-on favorite to win the Oscar, and if she were to win, she would be the second person to win for playing the character of Anita after Rita Moreno won the Oscar for Best Supporting Actress for playing the same role sixty years ago in the 1961 Best Picture-winning “West Side Story.”
Anita would join the hallowed halls of movie characters who have won multiple Oscars. Obviously, actors get nominated and win multiple Oscars all the time, but the characters they play sometimes get that same honor and receive multiple nominations. It is a feat that has happened sporadically across the ninety-four years of the Academy. Here is a comprehensive history of all the times a character has been nominated multiple times at the Oscars.
Two Actors, Different Movies
The first category I want to highlight is when two actors play the same character across two different movies. This is the category that Anita falls under.
Most of these cases are when a movie is remade, or the same source material is readapted, as is the case with “West Side Story.” The direct remake/reimagining causes for the same characters to reappear, and if that material was Oscar-worthy material before, it often is once that material is remade.
There are two cases where multiple actors won the Oscar for playing the same character – Ariana Debose hopes to make that three. The first is Vito Corleone, which Marlon Brando won for portraying in “The Godfather,” and Robert De Niro won for portraying the younger version of Vito in “The Godfather Part II.” The second character who won multiple Oscars is the Joker, which Heath Ledger won Supporting Actor for portraying in “The Dark Knight” and Joaquin Phoenix won Best Actor for playing him in “Joker.”
The earliest case of a character getting their second nomination is in a little-known movie and its remake; both titled “The Letter.” The first iteration of “The Letter,” an early sound picture, came out in 1929 and starred Jeanne Eagles as Leslie Crosbie. Eagles had died suddenly of a drug overdose months after the film had been released and was nominated posthumously for the role, and remains the only actress to be nominated posthumously in the category. Only 11 years later, “The Letter” was remade and earned Bette Davis a nomination for portraying Leslie Crosbie.
This year, Peter Dinklage was in the conversation for his performance in “Cyrano.” If he had been nominated, he would have been the third Cyrano de Bergerac to be nominated. The first was Jose Ferrer, who won for the role in the 1950’s “Cyrano de Bergerac,” and Gérard Depardieu was nominated for the 1990 French adaptation of the classic play.
Another classic that garnered multiple nominations is “Pygmalion,” which Leslie Howard was nominated for the 1938 version and when it was adapted into a musical called “My Fair Lady” in 1964, Rex Harrison won Best Actor for his portrayal of Henry Higgins (When compiling this list, I was shocked to find out Eliza Dolittle was not eligible because although Wendy Hiller was nominated for “Pygmalion,” Audrey Hepburn was not nominated for “My Fair Lady,” which is crazy to me). In a similar vein to “Pygmalion,” the non-musical original adaptation of “Goodbye Mr. Chips” earned George Donat an Oscar for his portrayal of Arthur Chipping, and when it was adapted into a musical, Peter O’Toole was again nominated for playing Mr. Chipping. Across the many adaptations of “Little Women,” Winona Ryder and Saoirse Ronan have both been nominated for playing Jo March. The novel “True Grit” by Charles Portis has been adapted to the screen two times. Both times, the actor playing Rooster Cogburn has been nominated. John Wayne earned his single Oscar win for playing Rooster, and in the 2010 adaptation, Jeff Bridges was also nominated.
While “Pygmalion/My Fair Lady” came close to getting two characters nominated for multiple awards (still reeling at the Hepburn non-nomination), there have been cases where movies have been able to accomplish this. The first case is Harry Segall’s play “Heaven Can Wait,” about Joe Pendleton, a boxer whose death is a clerical error in the afterlife, and must take over another body to continue his boxing career with his manager Max Corkle. The first adaptation of the play retitled “Here Comes Mr. Jordan” earned Robert Montgomery a nomination for playing Joe and James Gleason for playing Max. Warren Beatty adapted the play again in 1978, keeping the original title of “Heaven Can Wait” and changing the boxing to football. Beatty was nominated for playing Joe, and Jack Warden was nominated for playing Max in this version.
And perhaps the most successful remake in Oscar history, “A Star is Born,” has been made four times, each time earning Oscar nominations. The 1937 version earned nominations for Janet Gaynor and Frederic March for the leads. When it was remade in 1954, Judy Garland and James Mason again earned nominations. And although neither Barbra Streisand nor Kris Kristofferson is nominated for the 1976 version, Streisand still earned an Oscar in the form of Best Original Song. And finally, when Bradley Cooper remakes “A Star is Born,” both himself and Lady Gaga are nominated for the leads once again. Across the four movies, three movies earned its leading pair Oscar nominations (Also, while not an official remake, “The Artist” shares a lot of its DNA with “A Star is Born,” chronicling the rise of one star, the death of another, and the romance between them, as well as the old Hollywood pastiche at the center of all “A Star, is Born” movies. So, unofficially I’ll say that Jean Dujardin and Berenice Bejo have also both been nominated for very similar roles as the rest of the leading pairs of the “A Star is Born” movies).
And finally, some of the weirdest cases of characters receiving multiple nominations stem from the most adapted writer of all time, William Shakespeare. The most straightforward example is Laurence Olivier and Kenneth Branagh, both being nominated for their versions of “Henry V,” Olivier in 1946 and Branagh in 1989. In the next case, Basil Rathbone was nominated in 1936 for playing Tybalt in “Romeo and Juliet.” “West Side Story” is inspired by “Romeo and Juliet.” Many characters resemble their counterparts in Shakespeare’s original play, with Tony and Maria serving as “West Side Story’s” Romeo and Juliet. In 1961, George Chakiris won for playing Bernardo, the Tybalt character in the movie. And finally, in one of the edge cases of this phenomenon, Laurence Olivier is nominated for playing Othello in the 1965 adaptation. Earlier, in 1947’s “A Double Life,” Ronald Colman plays actor Tony John, who is offered the role of Othello in a new play with his ex-wife set to play Desdemona. Throughout his tenure of Othello, Tony takes on more and more of Othello’s personality, growing more and more jealous of his new girlfriend. He takes on more and more of Othello’s jealousy and rage until the film’s final moments, sharing its final climax with Shakespeare’s play, Tony kills himself. So while Colman is technically playing Tony, he is ostensibly playing Othello, earning Othello a place on this list.
Actors Playing Real People
The second instance where two actors could earn Oscar nominations for playing the same character is when they play a real person, and that person shows up in more than one unrelated movie. A lot of these skew newer, perhaps reflecting the Academy’s growing love for impersonation and playing real people.
The most recent example of this is Andra Day being nominated in 2020 for playing Billie Holiday in “The United States vs. Billie Holiday.” Diana Ross had already been nominated for her portrayal in 1972 for “Lady Sings the Blues.” Kirk Douglas and Willem Dafoe have both been nominated for playing Vincent Van Gogh for 1956’s “Lust for Life” and 2018’s “At Eternity’s Gate,” respectively. Leonardo DiCaprio plays Howard Hughes in 2004’s “The Aviator,” which earned him a nomination for Best Actor. Twenty-four years prior, Jason Robards plays Howard Hughes in a scene-stealing performance in 1980’s “Melvin and Howard” to earn him a nomination for Best Supporting Actor.
Two US presidents have earned multiple nominations. Anthony Hopkins plays Richard Nixon in Oliver Stone’s 1995 biopic “Nixon,” and Frank Langella plays the president in 2008’s “Frost/Nixon.” Daniel Day-Lewis earned his third Oscar for Best Actor for playing Abraham Lincoln in Steven Spielberg’s “Lincoln” in 2012, while Raymond Massey had already received a nomination 72 years prior for 1940’s Abe “Lincoln in Illinois.”
And finally, two real people have earned three nominations. Three actors have been nominated for playing King Henry VIII: Charles Laughton in 1933’s “The Private Life of Henry VII,” Robert Shaw, the one supporting performance of the three, in 1966’s “A Man for All Seasons,” and Richard Burton in 1969’s “Anne of the Thousand Days.” And Queen Elizabeth I has also nabbed three Oscar nominations. Two of which were played by Cate Blanchett in 1998’s “Elizabeth” and its 2007 sequel, “Elizabeth: The Golden Age.” And in 1998, the same year Blanchett was nominated for her first portrayal of Queen Elizabeth I, Dame Judi Dench won Best Supporting Actress for her performance as Queen Elizabeth I in “Shakespeare in Love.”
One Actor, Different Movies
So far, we’ve only looked at different actors receiving nominations for the same role, but throughout Oscar history, several actors have received multiple nominations for playing the same character.
A lot of these instances are when an actor returns to play the same character in sequels. The first time an actor was nominated for the sequel to a performance they had already been nominated for was in 1945. Bing Crosby won Best Actor in the highest-grossing movie of its year and Best Picture-winning “Going My Way” playing Father Chuck O’Malley, an informal young priest who clashes with the established, older Father Fitzgibbon. The following year, Bing Crosby returned as Father O’Malley in “The Bells of St. Mary’s,” the highest-grossing movie of its year (Bing Crosby really just dominated the box office and the Oscars in the 40s).
While Marlon Brando and Robert De Niro were busy winning Oscars as Vito Corleone in “The Godfather” and “The Godfather Part II,” Al Pacino racked up two nominations for playing Michael Corleone, winning neither (even despite the egregious category fraud for Part I, placing him in Supporting Actor. Although, I guess he did support both Vito Corleone’s to Oscar victory, so maybe in a way, he is supporting).
In one of the most extended gaps between a movie and its sequel, Paul Newman played Fast Eddie Felson in 1961’s “The Hustler,” but lost. Twenty-six years and five winless nominations later, Newman returns for the sequel, Martin Scorsese’s “The Color of Money,” earning his 7th nomination and his first Oscar win.
The most recent actor to receive a nomination for playing the same nominated character in a sequel, and from what I can tell is the only time an actor has been nominated for the seventh entry in a franchise, Sylvester Stallone has been nominated for playing Rocky Balboa in the highest-grossing movie of 1976 and Best Picture-winning “Rocky” as well as in 2015’s “Creed.” These remain Stallone’s only two acting nominations (receiving a writing nomination for “Rocky”), winning neither.
And it’s not only through sequels that one actor can receive a second nomination for the same character. Peter O’Toole accomplished this feat by playing King Henry II in two different movies. He was nominated for his role in 1962’s “Becket” and then again, six years later, for 1968’s “The Lion in Winter.”
So far, these have been relatively straightforward, but for the last two examples in this category, we enter the world of the edge cases; the technicalities and oddities of Oscar History.
I should say now that the title of this section is a lie. Although it makes sense that one actor would have to be nominated across two different movies to get two nominations, that is not technically the case. It is possible (and has happened once) for an actor to get multiple nominations for the same role in the same movie (and I’m not talking about cases like Nicolas Cage in “Adaptation,” playing multiple roles, because they end up still only getting one nomination).
In 1944, while Bing Crosby would get the first of his two nominations as Father O’Malley in “Going My Way,” Barry Fitzgerald didn’t bother to wait for a sequel to his two nominations; he got two nominations for playing Father Fitzgibbons, one in Lead and one in Supporting, which he would go on to win. He earned enough votes in both categories to earn a nomination. This is the only time this has happened, and the Academy quickly made a rule change to prevent this from happening again.
And finally, the case that is the largest stretch to consider the same role is for Charlie Chaplin. He often plays the same archetypal character in his movies, known as the Tramp. He plays this character in “The Gold Rush,” “City Lights,” and “Modern Times,” none of which earned him a nomination. Considering he’s one of the iconic figures in early Hollywood history, Chaplin has often been overlooked at the Oscars, earning only two acting nominations, one of which was taken away. In the first Academy Awards, Chaplin was nominated in three separate categories for 1928’s “The Circus,” Best Director (Comedy Picture), Best Writing, and Best Actor for playing The Tramp. Later, the Academy took his name off of the competitive categories and instead rewarded him with an honorary Oscar “for acting, writing, directing and producing The Circus.” Chaplin’s second nomination came in 1940 for his work in “The Great Dictator,” his first speaking role, though it was still largely silent. In the film, he plays two different characters, one is Adenoid Hynkel, a satirized version of Adolf Hitler, and the other is “The Barber,” a Jewish barber. While he is not named the Tramp and is not technically the same character, the Barber shares a lot of traits with the Tramp character and his look – the iconic mustache and bowler hat.
Two Actors, Same Movie
And finally, we have the rarest category of characters getting multiple nominations; two actors playing the same character at different ages within the same movie. It has only happened three times throughout the history of the Oscars, although one of the times is this year.
This year, Olivia Colman and Jessie Buckley are both nominated for playing Leda Caruso in “The Lost Daughter.” Olivia Colman plays the older version of the character, and Buckley plays the younger version in flashbacks.
In 1997, Kate Winslet was nominated for Best Actress for playing Rose in “Titanic,” while Gloria Stuart was nominated for Supporting Actress for playing the older version of Rose. And in the only other case of this phenomenon, Kate Winslet is again nominated for playing the younger version of a character, this time in Supporting Actress in 2001’s “Iris” while Dame Judi Dench earns a Best Actress nomination for playing the older version of Iris.
What does all this mean?
Are there any larger conclusions we can draw from looking at these 30 cases, or are they just a novel piece of Oscar trivia? Probably the latter, but there are two possible conclusions to draw from looking at how often this has happened in Oscar history.
The first is how much Hollywood is drawn to remakes, sequels, and adaptations. This is by no means a new observation; people have been writing about this for decades. But seeing some of these cases stretch far back into the past, with “The Letter” being remade in 1940, and “The Bells of St. Mary’s,” an Oscar-nominated sequel in 1945, shows that Hollywood has always been drawn to the same stories and films. For as long as we’ve been making films, we’ve been adapting Shakespeare, and “The Tragedy of Macbeth” this year shows us that we always will.
The second conclusion reflects what the Academy is interested in recognizing. There is no secret that the Academy loves to reward actors playing real, recognizable people. Acting is often misconstrued as impersonation, where it is more obvious to see how an actor has transformed, and the voters have something to compare it to. It often feels like an uphill battle to get nominated and even harder to win for an original character. The cases above showcase how often the Academy rewards performances that they have something they can compare it against. Several real-life people appear on this list, such as Abe Lincoln or King Henry VIII. Still, having multiple people play the same character across different films allows for the same kind of comparisons to be made, even with fictional characters. Joaquin Phoenix’s take on the character the Joker can be talked about in the same way as Rami Malek’s take on Freddie Mercury.
Do you think Ariana DeBose is winning the Oscar this Sunday for her performance in “West Side Story?” Check out the NBP Team’s predictions here and let us know your thoughts in the comments section down below or on our Twitter account.
You can follow Ryan and hear more of his thoughts on the Oscars and Film on Letterboxd at @rtoole
