10 Funniest Comedies of All Time

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When talking about the funniest comedies, I do like something different and challenging. Please do not get me wrong, I like to laugh as much as the next guy, but I like to laugh and be challenged, I like them to work for my laughs. Comedy is a genre but there are several sub genres under the comedy banner. We have my personal favorite black comedy, satire, screwball, farce, romantic, musical, slapstick, vaudeville-burlesque, political, and parody, a fairly new genre courtesy of Mel Brooks. And of course there are elements of comedy in almost every film ever made, if you look for them, but the truest comedies are made to make you more than just laugh. Chaplin believed the greatest comedies to be the ones that also make you think and perhaps cry. I do agree with that, because there is nothing more heartbreaking, or funny for that matter than a sad clown overcome by life. Far too often I am accused of preferring dramatic film to drama, and though I do enjoy dark tales, I also like to laugh, and laugh often. So here is the list of funniest comedies ever.

1. TOOTSIE (1982)


Not only is it the best comedy ever made, the finest farce ever put on film it is the greatest film made about the art and craft of acting ever made. Dustin Hoffman is astounding as Michael Dorsey, who when he cannot get work as an actor, as he argues with everyone he masquerades as a woman and finds work and great success as a woman, Dorothy Michaels. That he becomes a better man as a woman than he ever was as a man is something very special. Hoffman goes further than just acting…he becomes Dorothy in a way no other actor portraying the opposite sex has. Beautifully directed, written and acted by all. Hoffman’s performance is simply one of the greatest in the history of the cinema.

2. SIDEWAYS (2004)


Paul Giamatti should have won the Academy Award for his superb portrayal of Miles, a writer, school teacher and wine lover who is a sad sack disconnecting from life. Using wine as a metaphor for their lives, a group of four spend a week together before one of them will marry. The week will allow each to discover something about one another and Miles finds love again with Maya (Virginia Madsen). Thomas Haden Church is hilarious as his horn dog best buddy Jack. A superb film, with a quartet of excellent performances, fine directing and writing.

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