5. Step Brothers - I wasn't sure exactly what to expect from this movie, but from the moment Will Ferrell put his nuts on John C. Reilly's drum-set, I realized that this movie was one of the greatest comedies ever made. The way these two act like kids at forty is quixotic (ok, I just wanted to use that word, and I don't think it works in this context, but deal with it!) The only thing funnier than the Catalina Wine Mixer is how the characters talk so reverently about the Catalina wine mixer. Lastly, Will Ferrell, in a dream sequence, busting in on his therapist dressed like the Brawny Paper Towel Lumberjack is one of the funniest things I've ever seen.
4. Happy Gilmore - Adam Sandler killers me in this movie. I'm sure there are old school purists that are mad because I ranked Happy Gilmore above Caddyshack- well, unfortunately I really don't care. In fact, Just stay out of my way... or you'll pay! LISTEN to what I say! Seriously though, the price is wrong, bitch.
3. 40 Year Old Virgin - Steve Carrell is funny in this, but there's no chance this movie makes it this high without the cast of characters around him. Romany Malco (had to look up his name), Seth Rogen and Paul Rudd make this movie way better than it would've been otherwise. Hell, even the Pakistani guy who worked in the electronics store is hilarious. The advice "Be David Carruso in the movie 'Jade,' helped me get my fiance! (Could be true or not, who knows!)
2. Dumb and Dumber - Lloyd and Harry on the adventure of a lifetime. I remember seeing this in theatres and dying laughing. I recently bought the special edition DVD with some extra scenes and even those are great. It really sucks they didn't get on the bus with the bikini models at the end (sorry for the spoiler but seriously go see the movie already) but there's really no way those guys would get on the bus. They served the characters correctly by not allowing it. Even funnier, a guy from my high school said he has only cried at the end of two movies- Braveheart and Dumb and Dumber.
1. Anchorman: The Legend of Ron Burgundy - Was there any doubt? The first time I watched this movie, I thought, "It was pretty good." Now that I've seen it 80 times, I have to admit I still find new, subtle stuff to look laugh at. Try this one: When they announce Ms. Corningstone as the co-anchor everyone gets upset and most people focus in on Ron yelling about it. Look at the upper left corner of the screen and watch Paul Rudd do a cartoonish fake fainting. He puts his hand to his forehead and goes straight down. It's pretty damn awesome. There are tons of quotable lines and great characters to latch on to. Not many things are better than the street fight during the middle of the movie.
So that's my list. My apologies to Old School, Dirty Work, Talledega Nights, Airplane!, Naked Gun (1 and 2.5- I'm fairly certain G$ is going to kill me on that omission), and the countless others that I didn't squeeze in. Let me know what else I missed or just leave some funny quotes in the comment section.