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15 Actors Who Won An Oscar for The Wrong Film

15 Actors Who Won An Oscar for The Wrong Film

Winning an Oscar is almost as hard as it is to get nominated for one. Given the unpredictability when it comes for Academy voters to decide on the winners, not even the performances that critics predict will win are guaranteed the victory. 

The Academy has gotten it right and wrong when it comes to voting for the best performances across all four acting categories each year. In the times where the Academy was wrong, it happened either due to an upset victory and/or wanting to give a well-established actor a “Makeup” or “Career” Oscar. As a result, there have been several actors who have won the prestigious prize, but for the wrong films though. 

With that being said, listed below are 15 Actors Who Won An Oscar for The Wrong Film:

1. Leonardo DiCaprio:

There are tons of articles written everywhere regarding which films Leonardo DiCaprio should have won an Oscar for and which ones he was robbed of a nomination for. When he finally earned his Oscar for Best Actor for the 2015 film The Revenant, the Internet literally exploded.

While he gives the performance of his career as Hugo Glass, his win was more in recognition of the body of work he has done throughout his successful career. DiCaprio’s win came from his fifth Oscar Nomination for Acting (he has a sixth nomination for Best Picture as a producer). From his four other nominations for acting, DiCaprio should have won for his first one: Best Supporting Actor in the 1993 film, What’s Eating Gilbert Grape

In his breakout role, DiCaprio plays Arnie, the mentally disabled brother of the titular character (Johnny Depp). DiCaprio’s tragic-yet heartfelt portrayal of the character earned him rave review from critics and his well-deserved Oscar Nomination for Best Supporting Actor makes him one of the category’s youngest nominees ever (He was 19 years old). However, some can argue the Best Supporting Actor Category for films released in 1993 was one of the most competitive lineups ever as two of DiCaprio’s fellow Oscar Nominees included the eventual winner Tommy Lee Jones for The Fugitive and Ralph Fiennes for Schindler’s List

15 Actors Who Won An Oscar for The Wrong Film

2. Kate Winslet:

Just like her close friend and Titanic and Revolutionary Road co-star Leonardo Di Caprio (See #1 Above), Kate Winslet’s first and only Oscar win was well-deserved, but also long overdue. When she won Best Actress for the 2008 film The Reader, it was her first win from her sixth (eventually seven) nomination overall. 

In The Reader, her portrayal of a former guard at a Nazi Concentration Camp  earned rave reviews from critics. However, Winslet was more deserving of a Best Actress Oscar for her role as the neurotic and impetuous Clementine in the 2004 film Eternal Sunshine in Spotless Mind. Winslet, who’s known mostly her roles in historical dramas, was cast against type in the science fiction romance film. Unfortunately, her electrifying performance came in the same year that Hilary Swank won every Best Actress Accolade for Million Dollar Baby

15 Actors Who Won An Oscar for The Wrong Film


3. Marlon Brando:

From eight Oscar Nominations, the late Marlon Brando has won an Oscar twice, both for Best Actor: for the 1954 film On the Waterfront and the 1972 film The Godfather.

Although he gives a great performance in the former, Brando’s Oscar win (which was his first from a historic four consecutive nominations), felt more of like a compensatory Oscar after he had been overlooked for his first three nominations. His first win is considered an upset as Bing Cosby was expected to win that year for The Country Girl

While he 100 percent deserved his win for The Godfather, the performance Brando should get his first Oscar for should have been the one that gave him his first nomination: the 1951 film A Streetcar Named Desire. Based on the iconic play of the same name, Brando plays Stanley Kowalski (a role he played on Broadway), the brutish brother-in-law of the main character Blanche DuBois (Vivian Leigh) and husband of Blanche’s sister Stella (Kim Hunter). 

The 1951 film earned rave reviews, especially for the performances of Leigh, Brando, Hunter, and Karl Madden, the latter of whom played Mitch, a friend of Stanley’s who briefly dates Blanche. A Streetcar Named Desire catapulted Brando’s career and made him one of Hollywood’s male sex symbols. Brando’s performance is credited with promoting the idea that method acting as an acceptable style of acting and is considered as one of the greatest performances in modern film acting. 

At the 24th Academy Awards Ceremony, the film won 4 of its 12 Nominations and three of those wins were for acting: Best Actress for Leigh, Best Supporting Actress for Hunter, and Best Supporting Actor for Madden. However, the film was prevented of a clean sweep in the Acting Categories (something that has never been done) when Brando (the favorite to win) lost to Humphrey Bogart for his work in The African Queen. 

In a way, Brando’s win for the 1954 film On The Waterfront is also considered a “Makeup” Oscar as not only did he beat Cosby, but he also got a little bit of revenge as Bogart coincidentally happened to be nominated in that category for The Caine Mutiny

15 Actors Who Won An Oscar for The Wrong Film

4. Anne Hathaway:

Anne Hathaway has been nominated twice for an Academy Award: once for Best Actress for the 2008 film Rachel Getting Married and once for Best Supporting Actress for the 2012 musical Les Misérables. For the latter film, not only did she win sweep almost every single Best Supporting Actress Award for 2012 films, she won the Oscar as well.

Hathaway’s portrayal of Fantine, a prostitute dying of tuberculosis, in Les Misérables earned soaring reviews from critics, who all stated that her rendition of “I Dreamed A Dream” was one of the film’s best musical numbers. However, she should have won her Oscar for Rachel Getting Married, where she played Kym Buchman, a woman who is released from drug rehabilitation for a weekend so she can attend her sister Rachel’s (Rosemarie DeWitt) wedding. Hathaway’s raw and riveting portrayal earned her widespread recognition from critics.

As stated earlier, Kate Winslet (see #2 above) won that year as many felt that she had been long overdue of an Oscar as it was her first win from six nominations. Winslet’s performance is still worthy of an Oscar, but Hathaway’s in Rachel Getting Married by a slight edge, was much stronger. 

15 Actors Who Won An Oscar for The Wrong Film


5. Al Pacino:

Al Pacino is another actor who won an Oscar for the wrong movie as his win was considered a “Career Oscar” after being overlooked by The Academy for many years for his brilliant performances in the past. His only win from eight nominations was for Best Actor for his performance in the 1992 film Scent of A Woman. The 65th Academy Awards (where he also received a Best Supporting Actor Nomination for Glengarry Glen Ross, which he lost to Gene Hackman for Unforgiven), was also the most recent year Pacino was nominated.

In Scent of A Woman, Pacino plays Frank Slade, a retired army lieutenant who is blind and an alcoholic. While his performance is great, Pacino should have really won for either The Godfather or The Godfather Part II. His portrayal of Michael Corleone, whose transformation from reluctant family mobster to the ruthless don of the Corleone Crime Family is compellingly powerful.

His failure to win for the first two Godfather films is one of the biggest snubs in Oscars history. Pacino’s victory two decades later for Scent of A Woman is more like The Academy recognizing him for the brilliant performances he has given throughout his legendary career. 

15 Actors Who Won An Oscar for The Wrong Film

6. Sandra Bullock:

Bullock won an Oscar on her first try when she was nominated for Best Actress for the 2009 film The Blind Side. Her force-of-nature portrayal of the real-life Leigh Anne Tuohy, a white woman who adopts Michael Oher, a homeless African American high school football player who would later go on to be a Super Bowl Champion with the Baltimore Ravens, was impressive. However, it shouldn’t have been the film Bullock won for.

Instead, Bullock should have won for her more powerful performance in the 2013 Thriller Gravity. Given that her character is a space traveler stranded in space, Bullock was isolated and onscreen alone for most of the duration of the film. Despite this, Bullock carries the film with her ambitious performance. 

15 Actors Who Won An Oscar for The Wrong Film


7. Denzel Washington:

From eight Oscar Nominations for Acting (his ninth nomination was for Best Picture as a producer), Denzel Washington has won two times: Best Supporting Actor for the 1989 film Glory and Best Actor for the 2001 film Training Day. His first Oscar win was well-deserved but his second one was for the wrong film.

In Training Day, Washington plays Detective Alonzo Harris, a corrupt narcotics officer. Washington’s over-the-top performance and delivery are excellent, but his portrayal of Malcolm X in the 1992 film Malcolm X, deserved more recognition and a Best Actor Oscar Statuette. The performance which was robbed and should have won the Best Actor Oscar for films released in 2001 instead of Washington’s in Training Day was Russell Crowe’s (who won the previous year for Gladiator) in A Beautiful Mind

15 Actors Who Won An Oscar for The Wrong Film

8. Marisa Tomei:

Tomei’s Best Supporting Actress Oscar win for the 1992 film My Cousin Vinny is one of the biggest upsets in Oscars History. While her portrayal of Mona Lisa Vito, the fiancée of Vinny Gambini (Joe Pesci), is screen-stealing, Tomei should have won for a different film instead.

Since her surprising Oscar win, Tomei has received two more Best Supporting Oscar Nominations: for the 2001 film In The Bedroom and the 2008 film The Wrestler. The latter film is the one she should have received her Best Supporting Actress Oscar for. In The Wrestler, Tomei plays Pam/Cassidy, an aging stripper who Randy “The Ram” Robinson (Mickey Rourke), an aging wrestler, takes a romantic interest in. Tomei’s compassionate and open-hearted portrayal of her character and her ability to hold her own against Rourke definitely deserved more recognition. 

15 Actors Who Won An Oscar for The Wrong Film


9. Morgan Freeman:

At the 77th Academy Awards, the 2004 Sports Drama Million Dollar Baby won four of its seven nominations, including Best Picture, Best Director, Best Actress, and Best Supporting Actor for Morgan Freeman. This was Freeman’s first win from his then-fourth Oscar Nominations (He would later receive his fifth nomination for the 2009 film Invictus).

The latter’s portrayal of Eddie “Scrap-Iron” Dupris, the film’s narrator and boxing coach of Maggie Fitzgerald (Hilary Swank), is great but nowhere near as memorable as his performance in the 1994 film Shawshank Redemption. His delivery as Red, a prison contraband smuggler who befriends Andy Dufresne (Tim Robbins), the main character, stands out more to fans compared to his role in Million Dollar Baby. Freeman’s portrayal of Red is the beating heart of the movie and deserved to win the Oscar for Best Actor.

Had Shawshank Redemption been released any other year, Freeman would have hands down won. Unfortunately, it was released the same year Forrest Gump and Pulp Fiction was as Tom Hanks took home the prize for his role as the titular character in the former film.

15 Actors Who Won An Oscar for The Wrong Film

10. Whoopi Goldberg:

In the history of The Oscars, only a small number of actors have received an Oscar Nomination for his/her first major film role. One such performance that deserved to win but didn’t belongs to Whoopi Goldberg for her powerful portrayal of Celie Harris Johnson in the 1985 film The Color Purple

At the 58th Oscars Ceremony, the film was nominated for 11 Oscars, including Best Actress for Goldberg and Best Picture, infamously failed to win a single one. Today, The Color Purple, along with the 1977 film The Turning Point, still hold the record for the film(s) with the most Oscar Nominations without a single win. Although she won the Golden Globe for Best Actress – Motion Picture Drama, Goldberg should have taken home the Oscar that year as well.

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Goldberg’s win five years later for Best Supporting Actress for the 1990 film Ghost feels more of like a “Makeup” Oscar for the Academy’s failure to recognize her for The Color Purple. Her performance in Ghost as Oda Mae Brown is excellent, but nowhere near compared to her work in The Color Purple. 

15 Actors Who Won An Oscar for The Wrong Film

11. Meryl Streep:

Meryl Streep holds the record for the most Oscar Nominations for any actor/actress with 21 (4 for Best Supporting Actress and 17 for Best Actress). She has only one three times though. While her first two wins (Best Supporting Actress for the 1979 film Kramer vs. Kramer and Best Actress for the 1982 film Sophie’s Choice) were worthy of Oscars, her third win (Best Actress for the 2011 film The Iron Lady) should have been for a different film.

Don’t get me wrong, her portrayal of Margaret Thatcher is still worthy of an Oscar win, but she has several roles she could have received her third Oscar for that were much stronger than hers in The Iron Lady. Her win for that film was more for the fact it had been 29 years (at the time) since she last won one. 2011 was a stacked year for the Best Actress category, and the Oscar should have gone to either Streep’s fellow Oscar Nominee Michelle Williams for My Week Marilyn or Tilda Swinton for We Need To Talk About Kevin. Despite being nominated alongside Streep and Williams for a Golden Globe, SAG, and BAFTA Awards, Swinton was infamously snubbed of an Oscar Nomination that year. 

From the 18 roles she didn’t win for, the one Streep should have earned her third Oscar for was for the 2006 film The Devil Wears Prada. Her portrayal of Miranda Priestly, the ruthless editor of Runway Fashion Magazine is one of Streep’s most iconic roles and had the film been released any other year, she would have 100 percent won. Unfortunately, Streep would have to wait five more years to get her third Oscar as Helen Mirren swept the Best Actress Awards that year for her portrayal of Queen Elizabeth II in The Queen.

15 Actors Who Won An Oscar for The Wrong Film


12. Humphrey Bogart:

Bogart’s win is another classic example of an actor receiving a “Career” Oscar for the outstanding performances he/she has given in their long, successful careers in Hollywood. He still does an amazing job in The African Queen, but he should have gotten his Oscar for Best Actor in the 1943 classic Casablanca.

His victory for The African Queen is also considered one of the biggest upsets in Oscars History as up and coming star Marlon Brando (See #3 Above) was supposed to win the award for his stunning portrayal of Stanley Kowalski in A Streetcar Named Desire. Humphrey’s unexpected win also robbed A Streetcar Named Desire from becoming the first and only film to win all four Oscars for Acting (Brando’s co-stars, Vivian Leigh, Kim Hunter, and Karl Madden won the Best Actress, Best Supporting Actress, and Best Supporting Actor Categories respectively. 

15 Actors Who Won An Oscar for The Wrong Film

13. Julianne Moore:

The legendary actress finally won her first Oscar on her sixth nomination, which was Best Actress for the 2014 film Still Alice. While her portrayal of an Alzheimer’s patient was excellent, but when you compared that role to the other five she was nominated for, Moore could have won an Oscar much earlier.

From those five roles, she definitely should have gotten the Oscar for her role as Cathy Whitaker in the 2002 film Far From Heaven. Her portrayal of a 1950s housewife from a wealthy suburb in Connecticut whose “perfect” life begins to fall apart is one of the finest of her career. The role earned her a Best Actress Nomination at the 75th Academy Awards Ceremony.

Like how Al Pacino got two nominations for two different films at the 65th Ceremony (see #5 above), Moore was also nominated for Best Supporting Actress for her role in The Hours at the 75th Oscars Ceremony. Unlike Pacino, Moore failed to win either one she was up for. While she didn’t stand a chance against Catherine Zeta-Jones for Chicago in the Best Supporting Actress Category, she surprisingly lost the Best Actress Oscar to Nicole Kidman, her co-star from The Hours. While Kidman (See #15) was great in The Hours, many felt she was given a “Makeup” Oscar after losing the previous year for Moulin Rouge!.

15 Actors Who Won An Oscar for The Wrong Film


14. Henry Fonda:

The father of two-time Oscar Winner Jane Fonda, Henry Fonda is a Hollywood legend in his own right. He received his first Oscar Nomination (for Best Actor) for the 1940 film The Grapes of Wrath but didn’t get another acting nomination until 40 years later when he won for On Golden Pond (which daughter Jane also starred in and got a Best Supporting Actress Nomination for). 

The elder Fonda’s performance in The Grapes of Wrath is iconic and one of the best to not win an Oscar ever. James Stewart, the eventual winner for The Philadelphia Story, was shocked he had won as he voted for Fonda’s performance. Stewart even said he always felt like he only won because it was a compensation for not winning the previous year for Mr. Smith Goes to Washington

15 Actors Who Won An Oscar for The Wrong Film

15. Nicole Kidman:

Nicole Kidman won Best Actress for her portrayal of the mentally ill and depressed author Virginia Woolf in the 2002 film The Hours. It was her second (of eventually four) nomination overall. One person she beat was her co-star Julianne Moore (see above at #13), who was nominated (but lost both) for two Oscars that year: Best Supporting Actress for The Hours and Best Actress for Far From Heaven

However, Kidman should have won the previous year (her first nomination) for her role as Satine in the 2001 Musical film Moulin Rouge! Her Best Actress win for The Hours was more of The Academy giving her a “Makeup” Oscar after she failed to win for Moulin Rouge! Kidman lost to Halle Berry, who became the first African American to win Best Actress for the 2001 film Monster’s Ball

15 Actors Who Won An Oscar for The Wrong Film


Which films do you think that the Oscar Winners listed above should have for instead? Let us know your thoughts down below in the comments!

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