10 Comedy Movies That Prove Laughs Can Win Oscars

The Apartment (1960)

Billy Wilder’s bittersweet office comedy follows a lonely office worker who rents out his apartment to executives for their liaisons. Everything changes when he falls for the elevator operator who is involved with his boss. Witty, cynical, and surprisingly sensitive, this film combines romance and satire with perfection, winning five Academy Awards, including Best Picture, and becoming one of the greatest comedies of all time.

Annie Hall (1977)

This witty and neurotic romantic comedy reinvented the genre. It chronicles the complicated relationship between comedian Alvy Singer and free-spirited Annie Hall. It features stand-up comedy, audience addresses, and clever storytelling. It was iconic because of its charm and honesty. It also edged out 'Star Wars' to claim the Best Picture Oscar in 1978.

Birdman (The Unexpected Virtue of Ignorance) (2014)

Alejandro G. Iñárritu’s cutting Hollywood satire tells the story of a superhero actor trying to regain his artistic integrity by mounting a Broadway show. Filmed in a single, uninterrupted take, the movie combines its offbeat humor with the nervous energy of the showbiz world. Its sharp comedic wit about ego, fame, and artistic insecurity propelled it to the Best Picture win at the Oscars in 2015.

It Happened One Night (1934)'

This film, one of the original romantic comedies, is one of the screwball classics that brings together a runaway heiress and a cynical reporter on a crazy road trip that leads to romance through comedic misadventures. It made film history by winning all the “Big Five” Oscars, which are Best Picture, Best Director, Best Actor, Best Actress, and Best Screenplay, a rare occurrence indeed at the Academy Awards.

Everything Everywhere All at Once (2022)

This wildly inventive multiverse comedy combines absurd humor—hot dog fingers, raccoon chefs, and kung-fu mayhem—with emotionally resonant storytelling about family and identity. Michelle Yeoh stars as a laundromat owner who finds herself charged with saving the world. The Daniels’ genre-defying comedy was a cultural touchstone and swept the 2023 Oscars, taking home seven awards, including Best Picture.

The Sting (1973)

Paul Newman and Robert Redford star as suave con artists in this elaborate revenge scam in 1930s Chicago. With plenty of clever twists, humor, and ragtime music, this film offers one of the most enjoyable capers in film history. Its stylish and comedic approach to the genre helped the film garner seven Oscars, including Best Picture.

You Can't Take It with You (1938)

In Frank Capra’s delightful screwball comedy, a wealthy banking family clashes with a wildly eccentric family that values happiness over money. The culture clash leads to some very funny situations and some very poignant moral lessons about the importance of living freely. The movie won the Best Picture and Best Director awards at the Academy Awards.

Tom Jones (1963)

This raunchy, irreverent take on Henry Fielding’s novel traces the antics of a charming but irresponsible young man as he stumbles through love, scandal, and social mayhem. Famous for its snappy wit, violations of the fourth wall, and kinetic energy, this movie was remarkably up-to-date in its day, and it won four Academy Awards, including Best Picture, on the strength of its playful sensibility.

Shakespeare in Love (1998)

A romantic comedy that explores the way William Shakespeare got the inspiration for Romeo and Juliet. The movie combines historical fiction, comedy, and literary elements as Shakespeare falls in love with a woman who is disguised as an actor. The movie’s witty dialogue and charming performances surprised everyone as it won the Best Picture award at the 1999 Oscars.

The Artist (2011)

This lighthearted silent-style comedy is a tribute to old Hollywood, as told in the story of a silent screen star whose career is ruined by the advent of sound. Physical comedy and romance abound in this cleverly constructed picture that recreates the magic of old films. Its lighthearted tribute to filmmaking won five Oscars, including Best Picture.