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Comedic Performances That Were So Good They Even Won an Oscar

Comedic Performances That Were So Good They Even Won an Oscar

It took awhile for the motion picture industry to take comedy seriously enough to give it the Oscar respect that it deserved. It wasn’t until James Stewart won the Best Actor Oscar for “The Philadelphia Story” in 1941 that Hollywood finally gave some official love to a comedic performance. Not coincidentally, the film is considered one of the best romantic comedies of all time.

To determine the comedic performances that won Oscars, 24/7 Tempo reviewed data on Oscars history from the Academy Awards Database of the Academy of Motion Picture Arts and Sciences, considering movies tagged as “comedy” on IMDb, an online movie and TV database owned by Amazon.

Even after Stewart’s Oscar, the entertainment industry was slow to award the golden statue for comedic star turns. That began to change in the late 1960s. Walter Matthau, who appeared in four motion pictures on the list, won as Best Supporting Actor for “The Fortune Cookie” (1966), in which he co-starred with Jack Lemmon. (The film was the first of 10 comedic film pairings of Matthau and Lemmon.)

Actors and actresses won Academy Awards for three movies written by playwright and screenwriter Neil Simon in the 1970s – “California Suite,” “The Goodbye Girl,” and “The Sunshine Boys.” (These are the biggest all-time Academy Award winners.)

Performers won five Oscars for motion pictures directed by Woody Allen that appear on the list, starting in the late 1970s. Two of those awards went to Dianne Wiest, who won for “Bullets Over Broadway” and “Hannah and Her Sisters.” Speaking of that film, it also won an Oscar for Michael Caine’s performance.

Source: Courtesy of Fox Searchlight Pictures

23. Alan Arkin as Grandpa
> Film: Little Miss Sunshine (2006)
> Award: Best Actor In a Supporting Role

Alan Arkin earned his first Academy Award nomination in 1967 as a Russian navy officer trying to free his submarine, which had run aground in New England, in the Cold War farce “The Russians Are Coming, The Russians Are Coming.” He would earn four Oscar nominations in all, and won for his supporting role as the eccentric grandfather in the beauty pageant send-up “Little Miss Sunshine.”

Source: Courtesy of Miramax

22. Mira Sorvino as Linda
> Film: Mighty Aphrodite (1995)
> Award: Best Actress In A Supporting Role

Mira Sorvino won a Best Supporting Actress Oscar as an adult film actress and a working girl who is the birth mother of a baby adopted by a New York sportswriter (Woody Allen) and his wife. When the couple discover the boy is a genius, they set out to find the birth mother. Sorvino, daughter of actor Paul Sorvino, had earned her acting chops in previous roles in the indie film “Barcelona” and the Robert Redford-directed “Quiz Show.”

Source: Courtesy of Miramax

21. Dianne Wiest as Helen Sinclair
> Film: Bullets Over Broadway (1994)
> Award: Best Actress In A Supporting Role

Dianne Wiest’s second Oscar triumph came as the character Helen Sinclair in the Woody Allen-helmed “Bullets Over Broadway” (the first was for another Allen film, “Hannah and Her Sisters”). The plot involves a playwright (John Cusack) who makes a deal to cast a gangster’s talent-challenged girlfriend in a show so it can be produced. Wiest has been nominated for three Academy Awards.

Source: Courtesy of Buena Vista Pictures

20. Martin Landau as Bela Lugosi
> Film: Ed Wood (1994)
> Award: Best Actor In a Supporting Role

Baby boomers might remember Martin Landau for his clever masquerades on the television series “Mission: Impossible.” Landau won his lone Academy Award playing the aging and ailing horror actor Bela Lugosi in “Ed Wood,” the biopic about one of Hollywood’s worst directors, portrayed by Johnny Depp. Landau had been nominated for an Oscar twice before.

Source: Courtesy of 20th Century Fox

19. Marisa Tomei as Mona Lisa Vito
> Film: My Cousin Vinny (1992)
> Award: Best Actress In A Supporting Role

Marisa Tomei has been nominated for three Academy Awards and won her only Oscar to date with her first nomination, for her role as Mona Lisa Vito in “My Cousin Vinny.” She played the fiancée of a New York attorney (Joe Pesci) who defends his cousin and a friend wrongfully accused of murder in rural Alabama.

Source: Courtesy of Columbia Pictures

18. Jack Palance as Curly
> Film: City Slickers (1991)
> Award: Best Actor In a Supporting Role

Jack Palance earned two Best Supporting Actor nominations in the early 1950s for playing sadistic villains, roles enhanced by his intimidating size and menacing look. Palance won his lone Oscar for a comic role, though, playing a feisty, weathered cowboy who helps turn three urban denizens into cattlemen. When Palance won his Oscar, he did one-armed push-ups – at the age of 70 – on the stage.

Source: Courtesy of Metro-Goldwyn-Mayer

17. Kevin Kline as Otto
> Film: A Fish Called Wanda (1988)
> Award: Best Actor In a Supporting Role

Versatile actor Kevin Kline (“Sophie’s Choice,” “The Big Chill,” “Silverado”) won an Oscar for Best Supporting Actor in the zany comedy about diamond thieves looking to outscheme each other. The film’s star power included Jamie Lee Curtis and Monty Python comics Michael Palin and John Cleese.

Source: Courtesy of Metro-Goldwyn-Mayer

16. Cher as Loretta Castorini
> Film: Moonstruck (1987)
> Award: Best Actress In A Leading Role

In “Moonstruck,” Cher won the Best Actress Oscar playing a bookkeeper from Brooklyn who is conflicted when she falls in love with the brother (Nicolas Cage) of the man she’s supposed to marry (Danny Aiello). Cher previously was nominated for a Best Supporting Actress Academy Award for “Silkwood” in 1984.

Source: Courtesy of Metro-Goldwyn-Mayer

15. Olympia Dukakis as Rose Castorini
> Film: Moonstruck (1987)
> Award: Best Actress In A Supporting Role

“Moonstruck” holds the distinction of winning Best Actress and Best Supporting Actress Academy Awards for its stars Cher and Olympia Dukakis, respectively. Dukakis played Cher’s sardonic mother in the rom-com about an Italian family in New York. It was the only Oscar nomination for Dukakis.

Source: Courtesy of Orion Pictures

14. Dianne Wiest as Holly
> Film: Hannah and Her Sisters (1986)
> Award: Best Actress In A Supporting Role

Dianne Wiest has won two Best Supporting Actress Oscars for comedic roles in two Woody Allen movies. The first was for “Hannah and Her Sisters,” joining co-star Michael Caine, who won the Best Supporting Actor golden statue for the same film. Wiest has been nominated for three Academy Awards.

Source: Courtesy of Orion Pictures

13. Michael Caine as Elliot
> Film: Hannah and Her Sisters (1986)
> Award: Best Actor In a Supporting Role

Michael Caine, known for making British crime and adventure movies in the 1960s and 1970s, tried his hand at comedy, and won the first of his two Best Supporting Actor Oscars in Woody Allen’s “Hannah and Her Sisters,” a comedy about romantic complications involving three sisters. Caine has been nominated for six Academy Awards, the first in 1967 for “Alfie.”

Source: Courtesy of Orion Pictures

12. John Gielgud as Hobson
> Film: Arthur (1981)
> Award: Best Actor In a Supporting Role

John Gielgud was considered one of the three greatest British actors of the 20th century, along with Laurence Olivier and Ralph Richardson. Besides his storied tenure on the stage, Gielgud had a long motion-picture career that began in 1924 and ended only with his death in 2000. After receiving his first Oscar nomination in 1964 for “Becket,” Gielgud lampooned British propriety as the sarcastic butler in the comedy “Arthur,” starring Dudley Moore in the title role.

Source: Courtesy of Universal Pictures

11. Mary Steenburgen as Lynda Dummar
> Film: Melvin & Howard (1980)
> Award: Best Actress In A Supporting Role

After earning positive notices for her role in the time-travel adventure “Time After Time,” Mary Steenburgen gained fame for winning for Best Supporting Actress in the movie “Melvin & Howard.” She played the wife of down-on-his-luck Melvin E. Dummar (Paul Le Mat), who claims to have received a will naming him an heir to the fortune of Howard Hughes (Jason Robards).

Source: Courtesy of Columbia Pictures

10. Maggie Smith as Diana Barrie
> Film: California Suite (1978)
> Award: Best Actress In A Supporting Role

Long before she entertained audiences as the sardonic dowager in “Downton Abbey,” Maggie Smith won a Best Actress Oscar in 1979 for the Neil Simon-penned comedy “California Suite,” about the zany adventures of four couples in a hotel. Simon also won the Oscar for Best Writing.

Source: Courtesy of Warner Bros.

9. Richard Dreyfuss as Elliot Garfield
> Film: The Goodbye Girl (1977)
> Award: Best Actor In A Leading Role

The 1970s were a golden decade for Richard Dreyfuss, during which he appeared in such hits as “Close Encounters of the Third Kind” (1977), “Jaws” (1975), and “American Graffiti” (1973). He mined Oscar gold with “The Goodbye Girl” (1977), a rom-com written by Neil Simon. Dreyfuss has been nominated for one other Best Actor Oscar, for the 1995 drama “Mr. Holland’s Opus.”

Source: Courtesy of United Artists

8. Diane Keaton as Annie Hall
> Film: Annie Hall (1977)
> Award: Best Actress In A Leading Role

Diane Keaton not only won an Academy Award in her first nomination (she’s been nominated four times thus far), she became a fashion icon through her eccentric character’s menswear-inspired apparel. Keaton starred in the titular role as the girlfriend of Woody Allen’s character Alvy Singer.

Source: Courtesy of Metro-Goldwyn-Mayer

7. George Burns as Al Lewis
> Film: The Sunshine Boys (1975)
> Award: Best Actor In a Supporting Role

From vaudeville to radio to television to motion pictures, there wasn’t one entertainment medium where George Burns wasn’t successful. The venerable comedian and singer won an Academy Award as one half of a vaudeville act trying to reunite for a television special even though they dislike each other. Walter Matthau played Burns’ erstwhile partner and Neil Simon wrote the screenplay.

Source: Courtesy of Paramount Pictures

6. Tatum O’Neal as Addie Loggins
> Film: Paper Moon (1973)
> Award: Best Actress In A Supporting Role

Tatum O’Neal was the youngest person to win a competitive Academy Award as Addie Loggins, a pre-teen swindler trying to survive during the Great Depression in the film “Paper Moon.” She appeared in the movie with her father, Ryan O’Neal. To date, it is the only Oscar nomination and win for Tatum O’Neal.

Source: Courtesy of Columbia Pictures

5. Goldie Hawn as Toni Simmons
> Film: Cactus Flower (1969)
> Award: Best Actress In A Supporting Role

Goldie Hawn burst onto the entertainment scene as a member of the television ensemble comedy “Rowan & Martin’s Laugh-In” in the late 1960s. She turned to the big screen and won her lone Oscar thus far for Best Actress in the comedy “Cactus Flower,” which also starred Walter Matthau and Ingrid Bergman. Hawn, who would be nominated for a second Academy Award in 1981 for her role in “Private Benjamin,” has proven to be a bankable actor throughout her career.

Source: Courtesy of United Artists

4. Walter Matthau as Willie Gingrich
> Film: The Fortune Cookie (1966)
> Award: Best Actor In a Supporting Role

Walter Matthau crafted a memorable career as a grouchy middle-aged man put upon by the aggravation of modern urban life. He was nominated for three Academy Awards and won his lone Oscar for “The Fortune Cookie” in which he played an unscrupulous lawyer urging his brother-in -law (Jack Lemmon) to fake an injury. Directed by the great Billy Wilder, “The Fortune Cookie” was the first of 10 film pairings of Matthau and Lemmon.

Source: Courtesy of Warner Bros.

3. Jack Lemmon as Ensign Pulver
> Film: Mister Roberts (1955)
> Award: Best Actor In a Supporting Role

Eight-time Oscar nominee Jack Lemmon won the first of his two Academy Awards as Ensign Pulver in the star-studded naval farce “Mister Roberts.” Directed by John Ford and Mervyn LeRoy, the comedy starred James Cagney, Henry Fonda, and William Powell.

Source: Courtesy of Columbia Pictures

2. Judy Holliday as Billie Dawn
> Film: Born Yesterday (1950)
> Award: Best Actress

Judy Holliday was the first woman to win an Academy Award in a comedic role. Holliday played Billie Dawn, the unsophisticated girlfriend of an ambitious Washington-bound tycoon (Broderick Crawford) who hires a tutor (William Holden) to teach her proper manners. Garson Kanin wrote the screenplay for the film directed by the accomplished George Cukor.

Source: Courtesy of Metro-Goldwyn-Mayer

1. James Stewart as Mike Connor
> Film: The Philadelphia Story (1940)
> Award: Best Actor

Some movie fans think Stewart’s Best Actor Oscar for “The Philadelphia Story” was payback for him not winning the prior year for “Mr. Smith Goes to Washington.” George Cukor directed the screwball comedy, which also starred Katharine Hepburn and Cary Grant. Stewart would be nominated for five competitive Academy Awards (he won an honorary Oscar in 1985), but his triumph for “The Philadelphia Story” would be his only golden statue.

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