23 Brilliant Comedic Performances That Even Won an Oscar

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.”

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 discovers 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.”

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.

Baby boomers might remember Martin Landau for his clever masquerades on the television series “Mission: Impossible.” Landau won his lone Academy Award for 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.

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.

In the early 1950s, Jack Palance earned two Best Supporting Actor nominations 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.

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 out-scheme each other. The film’s star power included Jamie Lee Curtis and Monty Python comics Michael Palin and John Cleese.

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.

“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.

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.

Known for making British crime and adventure movies in the 1960s and 1970s, Michael Caine 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.”

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.

After earning positive reviews for her role in the time-travel adventure “Time After Time,” Mary Steenburgen gained fame for winning 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).

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.

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.”

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.

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.

The youngest person to win a competitive Academy Award was Tatum O’Neal for her role 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.

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.

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.

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.

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.

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.