Best Picture Oscar Comedy Winners

The Academy Awards have not been kind to comedies over the years. Of course the Best Film winning comedies are not necessarily the best comedies ever made. Of these Academy Award winning films, only three appear on the AFI list of 100 funniest movies ever, Annie Hall appears at 4, It Happened One Night at 8, and The Apartment at 28. This would imply both that the funniest movies do not get nominated and win, and that many of these films, though officially comedies, are more Dramedies, combinations of comedy and drama.

Of course it also spotlights that the Oscars are a snapshot in time. The Academy Awards honor the here and now; they award the movie of the moment. Looked at in retrospect many of these films do not compare with the awesome history that has become filmdom.

It Happened One Night (1934)

This is the first of the Oscar winning comedies, and one of the best. This is one of only four films to have swept the major categories winning for Best Picture, Best Director, Best Actor, Best Actress, plus Best Screenplay. This fantastic film stars Claudette Colbert and Clark Gable as a star crossed pair trying to get across the country without any money. This is the original road movie with two mismatched people trying to get from point A to point B with mayhem ensuing along the way. This film was so involved in the public’s psyche that because of one scene showing Clark Gable removing his shirt with no undershirt underneath, undershirt sales dropped almost in half.

You Can’t Take It With You (1938)

Another classic Frank Capra film about the small town man and woman, family, quirky characters, and their head on collision with and triumph over the real world. A film with a superb cast starring Jean Arthur, Lionel Barrymore, James Stewart as a misfit family of writers, dancers, and fireworks makers. They are brought together with a powerful traditional family to learn about each other through a young couple’s love. As with any Capra film friendship is the strongest tie and kindness is stronger and more worthwhile than all of the money and power in the world.

Going My Way (1944)

Bing Crosby as Father O’Malley a role he reprised for another Oscar nomination in The Bells of St. Mary’s. This gem of a film introduce the populace to a new friendly figure as Father O’Malley moves into the neighborhood to meet the local toughs and bring a spark to a parish oversee by a withered old priest. It also earned director Leo McCarey Best Picture, Best Director, and Best Original Story.

All About Eve (1950)

This is probably one of the sharpest and wittiest films ever written. Before this no one had ever heard ‘Fasten your seatbelts, it’s going to be a bumpy night!’ Betty Davis is scathing as the aging actress trying to stay at the top of her game. The rest of the cast is stellar as well as they either try to break her down, build her up, or leech as much as they can get. It even has Marilyn Monroe with a line or two. A magnificent movie depicting Hollywood on Hollywood.

The Apartment (1960)

This film stars Jack Lemmon as an ambitious young man who lends his apartment to executives for afternoon trysts. When he falls in love with Shirley MacLaine and realizes she is the boss’ mistress, he must decide between love and smart business. Shirley MacLaine is of course her zany self and the film is fresh and fun.

Tom Jones (1963)

This movie stars Albert Finney as Tom Jones an orphan who is raised by an English gentleman and goes off to find his place in the world. A well directed and well acted joyous romp through life trying on each shoe until the right one fits.

The Sting (1973)

The Sting is a beautiful, funny period piece. This film is all about the fun of the flim-flam. A genius of planning and execution as a group of scam artists led by Paul Newman and Robert Redford try to take a rich shark for a bundle. The ending makes it all worthwhile. Plus, the film has great music and great costumes.

Annie Hall (1977)

Quintessential neurotic New Yorker Woody Allen at his best exploring the differences between men and women and the way they feel about relationships. Diane Keaton makes a great foil for his neuroses.

Shakespeare In Love (1998)

This one seems somewhat out of place on the list. Not riotously funny, this one barely skated into comedy. Add in a strong Miramax election campaign and you have the Shakespeare in Love win. The film stars Ralph Fiennes and Gwyneth Paltrow as Shakespeare and his muse creating the tragedy Romeo and Juliet.