Top 5 in no particular order

It's a Mad Mad Mad Mad World (always near the top for me. No better cast ever assembled IMO. Buddy Hackett was one of the funniest men I have ever heard and Johnathan Winters played his part as well as I have seen any actor play a part)

Monty Python and the Holy Grail (I have a wooden Badger)

Papillon (who cares if he made it up)

The Great Escape (I like Steve McQueen)

Tommy Boy (Could get bumped out of the top 5 but I still haven't seen a funnier movie since)

The Sting (could get bumped out of the top 5 but I love the plot twists)

Others that might crack the top 5 depending on my mood.

Shawshank Redemption (has anyone made more movies than Morgan Freeman? Good thing he is such a great actor)

Mel Brooks History of the World Part One (Still waiting for part two)

Young Frankenstein (Gene Wilder is one of the best comic actors I've ever seen)

Blazing Saddles (More Mel Brooks anyone)

Braveheart (the Other Mel I am a fan of, this is his best)

Gladiator (Don't really like Russell Crowe but I really liked this one)

See no Evil Hear no Evil (Richard Pryor & Gene Wilder. See above comment on Wilder, and Richard Pryor paved the way for every black comedian to come after him. Plus he was just plain funny )

Oh, and I almost forgot

Schindler's List (and not for the reason you might think. The red coat was a thing of genius.)

There are more but these are all I could think of for now. I usually make it a point to watch each of these at least once a year.