Comedy gold: 20 funny films that won an Oscar

Given that the Academy seems reluctant to give comedies their time in the sun, it’s not surprising that those comedies that have been acclaimed and received nominations and wins have tended to be those with strong dramatic elements. An excellent case in point is Birdman, directed by Alejandro G. Iñárritu and starring Michael Keaton. It is a testament to superb acting, a reminder of how important good writing is to the cinema, and a paean to technical craft and mastery. It was nominated for numerous Oscars and took home four, including Best Picture and Best Director. 

Even though the Academy hasn’t tended to be very friendly toward comedies, it has been slightly more welcoming to musicals. Thus, it’s unsurprising that a film like Gigi, which blended those genres, did so well. It helps that it was directed by noted auteur Vincente Minnelli, who was famous for directing a number of beloved musicals throughout his career. It received numerous Academy Awards nominations, going on to achieve that rare feat of winning every one for which it was nominated, including Best Motion Picture and Best Director.  

The madcap comedy It’s a Mad, Mad, Mad, Mad World is an embarrassment of riches when it comes to on-screen talent. The film stars Spencer Tracy, Ethel Merman, Milton Berle, Sid Caesar, and Mickey Rooney, among others. Its story about a whole gaggle of people trying to recover a suitcase of stolen money is the stuff of which sublime comedy is made, and the cast is uniformly excellent. It would secure several Oscar nominations, though these were mostly in the technical categories. It would win only one of these, for Best Sound Effects. 

Morgan Freeman and Jessica Tandy deliver beautiful, heartfelt performances in Driving Miss Daisy. Based on the play of the same name, the film focuses on the extraordinary bond between an elderly Southern Jewish woman and Hoke Coleburn, the Black man who becomes her chauffeur. Though it hasn’t aged particularly well in its depiction of race, it was widely beloved at the time, and there’s no doubt that Tandy and Freeman give remarkable performances. Small wonder that Tandy won Best Actress and that Freeman was nominated for Best Actor, and the film secured several other nominations and wins, as well. 

If one genre reached its apogee in the 1990s, it would be the romantic comedy. The decade was notable for producing some of the best-loved and well-remembered examples of the genre, including As Good As It Gets.  The film is filled with some remarkable performances, but arguably the most notable are those from its leads, Jack Nicholson and Helen Hunt, who portray writer Melvin Udall and single mother Carol Connelly. Both were nominated and won in their respective categories (Best Actor and Best Actress), and the film was nominated for a host of other awards. 

Arthur remains one of the most enchanting romantic comedies of the 1980s, thanks to the charming performances from leads Liza Minnelli and the late Dudley Moore, who play a working-class American girl and the wealthy British playboy who falls in love with her. Though their romance is at the center of the story, revered stage actor John Gielgud portrays Arthur’s long-suffering valet Hobson.  Arthur got several nominations at the Academy Awards for 1981 and won two of them — one for Gielgud for his masterful performance and one for Best Original Song.

A Fish Called Wanda is a madcap heist comedy that stars some truly great comedic talent, including Kevin Kline, Jamie Lee Curtis, John Cleese, and Michael Palin. It’s fun and eccentric in a way that only British films can be, and it immediately enchants the audience with its story about several diamond thieves and their efforts to procure some valuable jewels, no matter who they have to deceive. It managed to notch several Oscars nominations — for Best Director, Best Original Screenplay, and Best Supporting Actor — though it would only win one, with Kline taking home the statue for Best Supporting Actor. 

During his decades in Hollywood, Billy Wilder showed himself to be a true virtuoso, able to direct and write in genres as different as comedy and film noir. Like so many of his other productions, The Fortune Cookie was directed and co-written by Wilder, and he was able to draw out some remarkable performances in this black comedy, particularly from both Jack Lemmon and Walter Matthau, who plays the duplicitous lawyer William H. "Whiplash Willie" Gingrich. Matthau would win the Academy Award for Best Supporting Actor, his only win (though he would be nominated twice more).

Part black comedy and part costume drama, Yorgos Lanthimos’ The Favourite  is exquisitely crafted and a fascinating look at the fraught relationship between Great Britain’s Queen Anne (Olivia Colman), Abigail Masham (Emma Stone), and Sarah Churchill (Rachel Weisz). These three actresses strike sparks off of each other from the moment they appear on the screen, and Lanthimos’ unique visual style adds an extra layer of bite to the film’s acidic sense of humor. It received a number of Oscar nominations, but it managed to win only one, for Olivia Colman, who received the Academy Award for Best Actress. 

Cher is one of those formidable talents who has repeatedly proven that she should never be underestimated or slotted into one particular category. She has delivered many remarkable film performances throughout her storied career, including in the romantic comedy Moonstruck,  in which she played the heroine Loretta Castorini opposite Nicolas Cage. It’s the kind of romantic comedy that manages to stay true to the conventions of the genre and exceed them, so it makes sense that critics would have so beloved it. It was nominated for several Academy Awards, though Cher was the only one to win, taking home the statue for Best Actress. 

The Coen Brothers have always excelled at crafting bleak and cynical comedies, and in Fargo, they managed to make arguably one of their very best films. Starring Frances McDormand as Marge Gunderson, it follows her as she investigates a murder and soon uncovers far more than she expected, revealing the darkness lurking in the American heartland. It’s one of McDormand’s best performances, as she perfectly captures Marge’s good nature and relentless detective work (to say nothing of her stern moral compass). It’s thus no surprise that she would take home the Academy Award for Best Actress. 

Peter Bogdanovich is at his directorial best in Paper Moon, which focuses on the strange relationship between con man Moses Pray and little girl Addie Loggins. Like many of the director’s other films, it features the perfect combination of comedy and drama, and real-life father and daughter Ryan and Tatum O’Neal make for a winning combination. The young Tatum gives a particularly inspired performance, so much so that she was nominated for and won the Academy Award for Best Supporting Actress. Paper Moon is the type of film that serves as a reminder that old-fashioned genres can still have an appeal even in later decades.

For many fans of classic Hollywood, Billy Wilder is the old-time director par excellence. Known for such daring films as Double Indemnity and Sunset Boulevard, he also proved remarkably adept at comedy, and no film illustrates this better than The Apartment. Featuring a love triangle among Calvin Clifford (C.C.), "Bud" Baxter (Jack Lemmon), Fran Kubelik (Shirley MacLaine),  and Jeff D. Sheldrake (Fred MacMurray), it has all of the quippy dialogue one expects of a Wilder. While it might not be quite as world-weary and cynical as some of the director’s other works, it is nevertheless a very adult sort of comedy dealing with extramarital affairs. Small wonder it went on to win several awards, including Best Picture and Best Director.

City Slickers is the perfect blend of Western and comedy, focusing on a group of middle-aged men from the city who go on a cattle drive hoping to find a new sense of meaning in their lives. Though all of the performances in the film deserve praise, special mention must be made of Jack Palance, the old hand. Of course, Palance was himself the star of several Westerns, which lent his performance an extra layer of complexity. It’s thus not surprising that he would go on to win Best Supporting Actor; in fact, his nomination was the only one the film received.

Little Miss Sunshine is a paradigmatic example of the indie comedy that was very much in its heyday in the late ‘90s and early ‘00s. Its plot is deceptively simple, focusing on a family’s attempt to get their daughter (a young and already brilliant Abigail Breslin) to a beauty contest. The film has a warmth and tenderness, even as it also doesn’t shy away from sadness. The cast is uniformly excellent, but the real standout is Alan Arkin as the grandfather. He would go on to win the Academy Award for Best Actor in a Supporting Role, one of the film's two Oscars (the other being Best Original Screenplay).

Roman Holiday is one of those gems from classic Hollywood that is the perfect mixture of cast, screenplay, and director. Audrey Hepburn stars as Princess Ann, a royal who has a brief fling with Gregory Peck’s American newspaperman. William Wyler shows his usual firm directorial hand, and the film is enchanting and light. Hepburn is also superbly cast as the royal, with her European glamor and undeniable star power. She would go on to capture an Academy Award for her performance, and the film also garnered two other Oscars for both the story and costuming. 

The Philadelphia Story is one of those films that is a true meeting of greatness, with renowned director George Cukor at the helm and screen luminaries Katharine Hepburn, Cary Grant, and James Stewart as three people entangled in a rather complicated love triangle. Everyone is at the top of their game. The film went on to earn several Oscar nominations for its year, including the big ones of Best Picture and Best Director. However, it only scored one win, which went to James Stewart for Best Actor (one of the two he would earn throughout his distinguished career).

If there was one director who seemed uniquely capable of capturing the heart of Americana, it was Frank Capra. He also had a remarkable talent for screwball comedy, as he showed in a number of his films, including You Can’t Take It With You. As with many other notable examples of the genre, this film shines due to the chemistry between leads James Stewart and Jean Arthur and the quippy dialogue. Both are perfectly cast, with Stewart playing Tony Kirby, the scion of a wealthy family, and Arthur playing Alice Sycamore, whose entire family is very loving but, to put it mildly, very odd. This lovely comedy even managed to take home the trophy for Best Picture. 

The 1930s was one of the golden ages for screwball comedy, and one of the most notable and celebrated examples of the genre is It Happened One Night. Directed by Frank Capra — one of classic Hollywood’s great directors — it focuses on the romance between Claudette Colbert’s socialite Ellie Andrews and Clark Gable’s reporter Peter Warne. There’s no denying the electric chemistry between Gable and Colbert, and Capra is at his very best in capturing their dynamic and the light spirit of the screenplay. It’s thus no wonder that the film did so well at the Oscars, winning Best Picture, Best Director, Best Actor, Best Actress, and Best Adapted Screenplay.

Everything Everywhere All at Once was the surprise critical darling of 2023. Focusing on Michelle Yeoh’s Evelyn Wang, the film is another instance of multiverse storytelling, as Evelyn finds that she is the one person who can keep the entire thing from collapsing under the assault of the being known as Jobu Tupaki. It expertly blends a number of genres, but a certain dark comedic streak runs through the entire film. Thus, it’s surprising how many Oscars it captured, including Best Actress for Yeoh and Best Picture, the most coveted award of them all.