29. Airplane (1980)
David and Jerry Zucker invented the idea of full-out movie spoofs, and no film of theirs was more hilarious than “Airplane”. Thirty years later, it’s still as funny and zany as ever, including some of the most quotable punch lines in all of movie history. (“Have you ever seen a grown man naked before Jimmy?”) This film is comedy gold, and will probably always remain one of the funniest movies ever made. Simply put, “Airplane” is awesome.
28. The Graduate (1967)
This is the movie that put both Dustin Hoffman and Mike Nichols on the map, and rightfully so. It’s funny and charming and it’s incorporation of a pop music soundtrack from Simon and Garfunkel was decades ahead of its time. Its story of a college student still not really knowing what he wants to do with his life is something that I think more of us than not can relate to, and no one else can really play the everyman like Dustin Hoffman. For a movie made in the late 60’s you’d be amazed to discover just how current it really is.
27. This Is Spinal Tap (1984)
Hands down, “Spinal Tap” is the best movie made about music ever. It’s a hilarious mockumentary about the implosion of a heavy metal band, and all the people they bring down with them. It’s too bad Rob Reiner had to grow up and start making more “serious” films, because he’s never been as good since his early days here, and with “The Princess Bride”. Pop this film in immediately, and whatever volume your T.V. will go up to, crank it up to that… plus 1.
26. Dr. Strangelove: Or How I Learned to Stop Worrying and Love the Bomb (1964)
Up to this point I don’t think that I’ve included any films by Stanley Kubrick, and there’s a good reason for that… his films all deserve to be at the top of everybody’s list. Despite not being the most prolific film director of all time, Kubrick never made a bad picture, he just made varying degrees of awesome ones. “Dr. Strangelove” not only has the best title of any other film in the history of cinema, it is the textbook definition of what a satirical and dark comedy should be. It’s beautifully shot in black and white, and even while it has you rolling on the floor laughing, it still finds a way to make you think at the same time.
25. Monty Python and the Holy Grail (1975)
Two great things always seem to come out of England, musicians and comedians. Monty Python might never have been as big as The Beatles, but they damn well should have been. Whatever The Beatles did for popular music, Monty Python did the same for comedy. They were a group that was always willing to push the boundaries of the socially acceptable and never let their self-respect get in the way of a good joke. Throughout their career they made one awesome T.V. series and a number of hilarious films. “Monty Python and the Holy Grail” is easily their crowning achievement. In Grade 11, my religion teacher had the balls to show us this film and somehow he and I were the only ones laughing, but we laughed our asses off. I know that doesn’t sound like the most impressive of endorsements, two people out of a roomful of twenty laughing, but you’ll just have to trust me. After all, most Catholic’s aren’t known for their spot on sense of humour.