Up in Smoke used to be hilarious. Of course, I was a pothead then, so not sure how well it would work on me now lol. 40Yr Old Virgin I would definitely put on a list for movies that have made me laugh the most/hardest. Clerks 1, while I enjoyed, I never found too hilarious. Clerks 2 on the other hand, absolutely hilarious. Zack and Miri? Ehh, wasn't all that for me. Not Another Teen Movie? I hate all those movies with the exception of like the first Scary Movie. Revenge of the Nerds I never cared for. American Pie was funny. Office Space was definitely funny. Jackass movies are pretty funny too (though some skits can be a bit of a miss).

A few I'd add: Grandma's Boy (hilarious), National Lampoons Christmas Vacation or just the regular Vacation. Grumpy Old Men is hilarious. I liked Ace Ventura. The Cable Guy. Old School. Dumb and Dumber. The Jerk. Elf. Bad Santa. Groundhog Day. South Park: Bigger, Longer and Uncut. The Goofy Movie. Meet the Parents. There's Something About Mary. Talladega Nights. Step Brothers. Billy Madison. Happy Gilmore. City Slickers. Tommy Boy. My Cousin Vinny. What About Bob. Uncle Buck.

Of course some of these were from when I was a kid and as we all know, stupid things can make us laugh as a kid. Oh, and I never got the appeal of Monty Python either.

I agree, Cat. Comedy is just so hard to rank like this because it's not timeless. Over the decades humor just changes. And once you've heard a joke so many times, it isn't funny anymore. Whereas, you look at something like a thriller and suspense is suspense. A well told murder-mystery is just flat out well told no matter what era you put it in. It's the reason classics like 12 Angry Men, Rear Window, Dial M for Murder, The Verdict, etc all remain relevant and still good to this day. They're timeless.

Even movies like Ben Hur and Lawrence of Arabia, epic like that hold fairly well today. Because an adventure is an adventure. An action is action. Though that genre and sci-fi, etc tend to have a bit of a weak side, being that genres like that are somewhat dependent upon special effects, etc. And with the advances in film technology it can be a bit of a strain watching an alien movie from today, then watching an old one to see how the UFO is clearly a carboard cutout hanging from string/rope. lol

What's funny today, though, won't be funny tomorrow. It's the same thing as how once you hear a joke about 100 times it just ceases to be funny. You can narrow it down to just physical comedy and see how it's changed. At first it was funny trying to see the skinny man lift a big barbell. Then that got old and it was funny seeing a man step on a rake. Then it was slipping on a banana peel, then it was slapping each other around or poking each other in the eyes. But we've seen that all now and that physical comedy isn't as funny. So then we get the World's Funniest Nut Shots. Then when that gets old we move on to some seriously out there physical comedy like the Jackass crew.

There's a reason you won't see many comedies topping the all-time greatest movies lists. And the ones you do are either there because they influenced the genre in a big way or were the best movie from a comedic legend (Groucho and Marx, Chaplin, Buster Keaton, etc) or, most likely, they're a romantic comedy (where the love story really carries the movie). And, aside from some of the romantic comedies, none are really timeless.

Like Cat said, comedy isn't timeless. And, as I pointed out, it's because you can't keep laughing at the same joke over and over again. I mean, I'm sure everybody has heard the "Who's on first?" skit a million times by now. Back in the day, that was hilarious. Go back and watch it now (especially now that you have heard the skit a million times) and honestly, can you even bring yourself to muster a grin anymore?

Sorry, that reply got real long, real fast lol.