Imagine a Marvel-style multiverse not filled with alternate versions of various superheroes but instead populated by iconic films whose casting ended up different. Think Tom Selleck’s Indiana Jones making it to the big screen instead of Harrison Ford. Or a world where Anthony Hopkins didn’t play Hannibal Lecter.
Film history is littered with various inflection points where legendary actors almost turned down or walked away from roles that would go on to change their careers forever.
Perhaps most surprisingly, there are multiple instance of actors nearly turning down roles that would go on to win them Oscars (or at least nominations). Hindsight, as they say, is 20/20 and these near misses almost always serve to underscore just how miraculous it is that so many great movies end up making it to the big screen at all.
Read on as we explore how some of the most iconic Oscar winning performances never happened.
1. Gwyneth Paltrow in Shakespeare in Love
A controversial Oscar-winner for a myriad of reasons, it seems strange to imagine that Shakespeare in Love was almost without eventual Best Supporting Actress-winner Gwyneth Paltrow. In an interview with Variety celebrating the films 30th anniversary, Paltrow noted that Julia Roberts was supposed to star in the role of Viola De Lesseps after Paltrow turned the role down citing issues in her personal life.
“I was in the middle of a terrible breakup and the idea of going to England and being far from home just seemed … I didn’t even read it,” she said. “I was just like, ‘I can’t read anything right now. I’m having a really hard time.'”
Thankfully, the version of the film that would have starred Julia Robert’s fell apart and Paltrow reconsidered taking the role. The 1993 period drama, which tells the story of William Shakespeare’s love affair with Paltrow’s character, would ultimately go on to win numerous Oscars including Best Picture, which it controversially won over Saving Private Ryan.
“It just changed my life,” Paltrow said about the impact the role had on her life. “I don’t think it ever went back to normal.” The win prompted a rethink of her career which, as Paltrow notes, “ started a whole series of thinking about what I wanted to do with the rest of my life.”
Following her Oscar-winning turn, Paltrow would go on to star in Wes Anderson’s acclaimed comedy-drama The Royal Tenenbaums, and bag the role of Pepper Potts in the Marvel Cinematic Universe.
2. Emma Stone in La La Land
One of the great films of this century so far, La La Land is an unabashed love letter to the golden age of the Hollywood musical. Bright colours, catchy songs and an undeniable charm are all key ingredients in its box-office and Oscar success.
However, it’s arguably Emma Stone’s remarkably vulnerable and charismatic lead performance as Mia that elevates the film to the same level as those that inspired it. It was a performance we almost never got to see thanks to, of all things, the musical Cabaret.
“The idea of doing another musical was like, ‘You’ve got to be out of your mind’,” Stone noted in an interview with The Hollywood Reporter. “After Cabaret, I wasn’t sure I would ever sing or dance again.” At one point, La La Land was supposed to feature Emma Watson in the Mia role alongside Miles Teller.
But director Damien Chazelle knew who he wanted and eventually convinced Stone to take on the role. Since her Oscar-winning turn in La La Land, Stone has been incredibly selective about the roles she takes, working with directors like Yorgos Lanthimos and Ari Aster and eventually winning her second Oscar for Poor Things in 2023.
3. Jack Nicholson in One Flew Over the Cuckoo’s Nest
It’s hard to imagine a world where Jack Nicholson didn’t play the role of McMurphy in the 1975 film One Flew Over the Cuckoo’s Nest, but Nicholson wasn’t immediately sold on the role. Based on the novel of the same name by Ken Kesey, the film tells the story of McMurphy and his time incarcerated at a mental institution after faking a mental illness to get out a long prison sentence. What follows is a dark and tragic journey into that is equal parts poignant, heartbreaking and hilarious.
Fearing the subject matter of the novel and his inability to live up to the source material, Nicholson initially turned down the role. However, director Miloš Forman eventually convinced him to change his mind and the pair, alongside an incredible ensemble that included Louise Fletcher as the villainous Nurse Ratched, would go on to make a true masterpiece.
The role would ultimately win Nicholson the first of three Academy Awards and given the films striking tone its hard to see how anyone else could have done justice to McMurphy’s anarchic presence. It ultimately cemented Nicholson as one of the great actors of his generation and led to a career that would include nine Oscar nominations outside of those three wins.
4. Gary Oldman in Darkest Hour
We can imagine even an actor of Gary Oldman’s calibre would have to think twice about portraying a man as famous as Winston Churchill, so it’s no surprise to find out that he initially turned down the role.
Concerns over the weight of the role and his own likeness to the famous prime minister led to Oldman saying no to the role. It wasn’t until director Joe Wright and producer Douglas Sabansky sold the actor on their take on the famous politician’s life that Oldman was won over.
By telling the story of a few weeks in Churchill’s tenure as prime minister instead of trying to cover the breadth of his life, Oldman was able to find a unique way into the character. Combine that with some incredible (and Oscar-winning) make-up effects and you’ve got a recipe for a magical performance.
Oldman embodies the man right up to his most famous speech to parliament after the Dunkirk retreat. The role would go on to earn Oldman acclaim and land him an Oscar, putting the beloved British actor known largely for supporting roles front and centre.
5. Sandra Bullock in The Blind Side
The controversial sports drama may have seen the comedic genius that is Sandra Bullock earn critical acclaim and a best actress Oscar, but she very nearly turned it down. Playing Leigh Anne Tuohy wasn’t an easy yes for Bullock, who was concerned about the characters devout faith. Eventually, Bullock met with the real Tuohy and was convinced to take on the role.
It ended up being an interesting year for Bullock who won both an Oscar and a Razzie in the same year, a feat few have achieved. After The Blind Side, Bullock would take on more dramatic roles, including the lead in the acclaimed thriller Gravity and the sci-fi film Bird Box. Don’t worry, she’s still got plenty of comedy on her resume too.
6. Kieran Culkin in A Real Pain
Jesse Eisenberg’s 2024 comedy-drama was anything but a pain thanks, in part, to the films co-lead in Kieran Culkin. Coming off the back of the intense and just plain tense world of Succession, Culkin originally tried to back out of the role in the film.
Eisenberg also had serious reservations about casting a non-Jewish actor in the role due to the films subject matter. In the end, Eisenberg picked Culkin, who reluctantly signed on to the film.
Culkin would go on to win the best supporting actor Oscar after an awards seasons sweep, thanks to his emotionally rich and charismatic performance in the film. That added an Oscar to the actors mantle alongside the Emmy he won for his role in Succession.
Since his win, Culkin has been relatively quiet, however he is set to return to the big screen in a the role of Caesar Flickerman in The Hunger Games: Sunrise on the Reaping later this year.
7. Julie Andrews in The Sound of Music
Julie Andrews might have only been nominated for her starring role as Maria in The Sound of Music, losing out to Julie Christie, but, given the fact that she almost turned down the iconic role, we had to include it. That’s right – Julie Andrews almost turned down the opportunity to take to the hills of Austria and bring them to life with her fabulous voice.
As she notes in her biography, after winning the Oscar for Mary Poppins just a few years prior, Andrew’s worried that she’d be type cast in nanny roles should she chose to take on the role of Maria.
Eventually, Andrews reconsidered, after being convinced in part by the film’s director Robert Wise, breathing life into what would become one of her most iconic roles.
She wasn’t typecast in the nanny role after all, instead becoming known for her effervescent screen presence and hit-making voice. She may not have won the Oscar – but she probably should have (sorry Julie Christie).
8. Audrey Hepburn in Breakfast at Tiffany’s
While Hepburn didn’t ultimately win the Oscar for her role in Breakfast at Tiffany’s, it is one of the actress’s most famous roles and, given the fact she nearly turned it down, we think it counts.
Hepburn took a while to accept the role of Holly in the film after being concerned she wasn’t right for the part. Concerns shared by author Truman Capote, upon whose book the film is based. Initially, filmmakers wanted Marilyn Monroe for the role, but the iconic actress turned them down.
Thanks to the film’s director Blake Edwards, Hepburn eventually stepped in and said yes to the role and the rest is history. It has since gone on to become a role synonymous with Hepburn and her particular charm as an actress and landed her the fourth of her five Academy Award nominations.
While she, like Julie Andrews, didn’t win for the role, it’s hard to argue that Breakfast at Tiffany’s didn’t have a monumental impact on Hepburn’s career going forward.
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