1) Happy Gilmore - Here it is, the funniest movie ever made! Caddyscak is NOT the funniest golf movie, no matter what the old-timers say. Non-stop laughes the entire way through, from the nursing home orderly to Chubbs' hand to Bob Barker beating up Adam Sandler. The pinnacle of Happy Gilmore's career, and a movie that will never be duplicated.
Nursing home orderly (Ben Stiller) - Okay, listen up everybody! Turn up your volumes, announcement. I got good news. We're extending arts and crafts time by four hours today!
Old lady - My fingers hurt.
Orderly - (softly) What's that?
Lady - My fingers hurt.
Orderly - Oh, well, now your back's gonna hurt, cuz you just pulled landscapin' duty. Hmm, anybody else's fingers hurt? I didn't think so.
Grandma - Sir, um, could I trouble you for a glass of warm milk? It helps put me to sleep.
Orderly - You could trouble me for a glass of warm milk. Now you will go to sleep, or I will put you to sleep. Check out the nametag. You're in my world now Grandma.
Grandma - Oh dear.
2) Office Space - By far the most low-budget film on the list, and the most subtle. You have to watch it at least thirty times to catch all the pauses and facial expressions that make this movie so ingenious.
"PC lobe letter? What the f*ck does that mean?"
"Yeah, hiii. It's Bill Lumberg again. Uhh, I just wanted to make sure you knew that we did start at the, uhh, usual time this morning. Yeah, it isn't a half day, or anything like that."
3) Austin Powers 2: The Spy Who Shagged Me - Even better than the first. Mike Myers proves his comic genius, playing three of the funniest characters ever created.
- Do you remember me Austin Powers?
- I don't recall your name, but your...fez...is...familiar.
"Number Two, you look so young, vital. Frau, you look so...riiight..."
4) Meet The Parents - The second movie in a row for Owen Wilson and Ben Stiller, who is in three of the top five. Mob boss Robert DeNiro also shows his funny side. The volleyball scene is possibly the funniest in history.
“You gave me life, you gave me milk, you gave me courage. You name was Angela, an angel from Heaven. But you were also an angel of God, and he needed you too. Selfishly, I tried to keep you here, while the cancel ate away your organs, like an unstoppable rebel force. But I couldn’t see you, and I shall see your face, never more…never more…never more…until we meet again in Heaven.”
Greg Fokker - So what got you in to, uh, carpentering?
Kevin - Carpentry? (smug laugh) I guess I’d have to say Jesus. He was a carpenter and I just figured if you’re gonna follow in someone’s footsteps, who better than Christ?
Jack – Greg’s Jewish.
Kevin – Are you?
Fokker – Yeah.
Kevin – Well so was J.C. You’re in good company.
5) Zoolander - If the whole movie were as funny as the first half hour, it would be number one on the list, hands down.
"You can derelict my balls, capi-tan."
"Hansel, so hot right now...Hansel."
6) The Original Kings Of Comedy - The funniest standup comedy piece ever, with the possible exception of Chris Rock's HBO specials.
"Sh!t, I wish a muthaf*cka would be in my muthaf*ckin' seat"
"A black President? Now come on y'all, we got Clinton, that's close. He got ***** tendencies."
7) Money Talks - The second Chris Tucker movie in a row, and the most underappreciated movie on the list. Far better than the black-and-white buddy flicks that have come out recently.
- I was there when they shot Baby Bro in MacArthur Park.
- Where’d they shoot him?
- In MacArthur Park you big dumb mutha-
- Nah, where’d they shoot him?
- In the @ss! Everybody knows Baby Bro got shot in the @ss!
"Well, you know, I had a lot of friends. Frank Sinatra, Jr., Sammy Davis, Jr., Jr., used to call me all the time."
8) Friday - Chris Tucker's first big movie, when he was at his best, before he started doing PG-rated blockbusters at $20 million a pop.
"Every time I come in the kitchen, you in the kitchen. In the godd@mn refrigerator. Eatin' up all the food. All the chicken. All the pig feet. All the collard greens. All the hog maw. I wanna eat some of them chitlins! I like pig feet!"
- My neck! My back! My neck and my back! Oww, I want a hundred and fifty thousand! But we can settle out of court right now for twenty bucks.
- Man, get yo' punk @ss up! It ain't even wet over here. D@mn!"
- Hey, well look here man. Just gimme ten dollars and I won't say nothin'.
- Get out.
- Two-fifty and a jawbreaker?
- Get out!
- A dollar and some envelopes?
9) Monty Python And The Holy Grail - Fine, one movie made before 1990.
King - Please! Please good people! I am in haste. Who lives in that castle?
Peasant 1 - No one lives there.
K - Then who is your lord?
P1 - We don't have a lord.
K - What?
Peasant 2 - I told you, we're an anarco-syndicalist commune. We take it in turns to act as a sort of execut