I could kick myself for not giving This is Spinal Tap at least an honorable mention here, because it belongs on the list. The irreverance, musical lampoonery, and comedy make it at least one of the top 5 comedies of all time. But there are some darn good choices on this list, regardless.
Annie Hall: This is a phenomenal movie, besting Star Wars in 1977 for Best Picture. Arguably one of the best ever, and certainly Woody Allen's best. Some of the most memorable quotes, at least for me, stick out here, such as Allen's character quipping, "My grandma never gave me gifts, she was too busy getting raped by Cosacks", and Hey, dont knock *********ion! Its sex with someone I love!", are quips that still make me laugh. I feel this film will be forgotten and overlooked due to it being a 70's film, but it's near the top for me.
Monty Python and the Holy Grail: Another 70's film that Im sure most people here HAVE seen. Using the the comedic style of talking in circles that most comedies dare not attempt, Monty Python uses insanely ridiculous situations and characters that Ive yet to see duplicated. The use of comedy in the background such as people slamming cats against the wall for no reason and people feeling up baskets of mud in fields are quite strange and hilarious at the same time. What makes this movie hard to vote against is that the same actor plays several different characters in the same movie, some quite different from the other, yet equally funny, something that likely will never be duplicated. Likely my pick.
Airplane: "Looks like I picked the wrong week to quit smoking. Looks like I picked the wrong week to quit drinking. Looks like I picked the wrong week to stop sniffing glue. Looks like I picked the wrong week to quit amphetamines." The legendary Lloyd Bridges quotes in this movie never fail to make me laugh, and he wasn't even a central figure in the 1980 movie. Without a doubt responsible for creating the genre of spoof movies with its irreverent satire of the multitute of disaster movies from the 70's, Airplane has no real discernable plot, and it doesn't need to. It's just funny from start to finish. This one could give Monty Python a run for its money, and possibly tops it. I literally laughed from start to finish.
Ghostbusters: Like "Holy Grail" its charm is in referencing a mature world of slightly twisted forces, keeping some constant. Its a familiar place, naturally found. Its that natural access that makes it so endearing. Nothing is forced; no one is trying very hard. They go there easily and we do as well. Very rarely can you pull off a successful blend of two separate movie genres,but Ghostbusters did it extremely well Its a very good comedy, not great though.
Ferris Beuller's Day Off: More than twenty five years after its release, this movie is something of a cult classic about one young man's struggle to take it easy. It's funny, dont get me wrong, but it's not a classic by any means. The accident is decent, and Matthew Broderick does a decent job as Ferris, and Alan Ruck as his neurotic friend. His girl is eye candy, nothing more. I liked this movie, but its a step below Ghostbuster's, and well below Monty Python, Annie Hall, and Airplane. It has its iconic quotes and all, but the movie overall didnt have me laughing throughout.
Dr. Strangelove: Well before my time, and Ive never watched the movie for whatever reason.
The Big Lebowski: As with many other films by the Coen brothers, The Big Lebowski is an odd array of out of the ordinary characters slapped right in the middle of an improbable situation. The Dude is an unlikely hero living in the city of Los Angeles who becomes embroiled in a botched kidnapping. This is not the average kidnapper comedy that has been seen a thousand times before. The Coen brothers take a fresh look at an old tired subject. The story they have created is intriguing and entertaining, but the true entertainment comes from the unique characters. As well as these characters are written, they would not be as effective had they been played by other actors. The roles seem to have been written for Goodman, Buscemi, and Bridges. Seeing Bridges step out of his usual serious persona is incredibly entertaining. The Big Lebowski is not for all tastes, but, if you get it, is one of the most engaging and side-splitting films around, and one which is eminently quotable, but it's not as funny as some of the others.
Monty Python's Life with Brian: If the "Holy Grail" is their funniest movie, "Life of Brian" is the most well-made. And here it is easier to sort through the sketches and jokes scattered around the film, because it does tend to get boring at times. Its utter irreverance and controversy, along with it still seeming reverant after 25 years makes it a good comedy, but it's not great. The jokes are more accessible and less tongue in cheek, but it truly bored me at times.
The Producers: I didnt make it through either version of the movie, as Im just not a fan of musicals.
There's Something About Mary: Im not a fan of Ben Stiller whatsoever, but I did find this movie to be funny. The gross out jokes are typical Farrelly brothers humor. but it does have a certain char to it, and Cameron Diaz is a big part of that. But the plot is nothing we haven't seen before, although it's overshadowed by some decent laughs. But it doesn't belong on the list of all-time greats, as funny as it is.
American Pie: Probably the best teen sex comedy flick. There are moments in the movie where the guys and gals have revelations of true sincerity, but then are quickly overshadowed by raunchy comedy. This film will undoubtably be remembered for several scenes of debauchery, such as the pie scene and the Jim/Nadia scene, but it relies too much on cheap laughs at times, but the laughs started and ended with sex and debauchery. That leaves it without the well-rounded humor that some of the best comedies of all time have.
The Hangover: I laughed, harder then I thought I would. The irresponsible man in peril has been played out, especially by Judd Apatow and his clan. But what made it funny is that the viewer doesn't have to follow the antics of grown up men getting in all kinds of mischief, rather, we see the effects of the night in question, many of which are quite hilarious. The movie is moronic at times, but isnt without its charm. But it's not a movie that Ive ven bothered to see more then once, because it wasn't that funny.
Dumb & Dumber: I can't stand Jim Carrey, but I did find this film to be 2 hours of escapism humor. There are good laughs watching the dumb idiot friends bumble their way from one idiotic situation to another. It's definitely not the most intellectual humour but it easily gets you laughing, poor taste or not. I don't see this as being near a classic comedy though.
Groundhog Day: Ive always seen this as more of a light comedy, moreso a charming drama/romance with some marginal laughs, but Ive never seen this as an out and out comedy. You would think a movie of reliving the same day over and over would get repetitive, but Groundhog Day is full of ingenious ideas. It successfully throws up new developments and delightful twists at every opportunity. The film is laced with memorable dialogue, and Murray gets to play one of the defining roles of his career as a facetious, sharp-tongued misanthrope who ultimately learns the error of his ways. But I never looked at this as a true comedy, in all honesty.
Caddyshack: This film is a classic, for sure. This comedy is extremely dirty and raunchy even by today's standards. The raunchiness has worn off with time and some of the take-offs are not so obvious to future generations but some of these lines have become well known jokes among some. Part of the reason this movie works so well is the jokes are rapid fire. They just hit you with one line after another. Another thing about the characters in the movie is that they seem so real. Today a lot of characters in comedy films are cardboard characters, ones we've seen before in one way or another. All of the characters here are written so nicely and believably and this is something very rare in modern comedy. And there are so many classic scenes in this movie. Among my favorites is the boating scene, the swimming pool scene, and when we see Rodney Dangerfield's golf bag phone. It doesn't best Airplane or Monty Python, but it's among the best of all time.
I'm likely going to go with Airplane here. While Monty Python will likely be the consensus winner, Airplane's dialouge, satire, and humor from start to finish will likely sway me, unless I can be convinced otherwise.