The hardest I ever laughed was ...

For me it was probably the time in third grade when Billy DiNardo told Helen Keller jokes during lunch.

 

I watched the first showing of the Dangerfield's showcase which was the first time Dice was on HBO. I was 14 or so, so I was the clear target audience. My jaw was on the floor.

It's too bad he stole most of them from Otto and George.

 

Seeing "Monty Python and the Holy Grail" in the theatre at 14 with no idea what we were walking into.

Seeing "Animal House" in the theatre (all 30 or so times)

"A Fish Called Wanda", especially Cleese stripping while spouting Russian and the family comes home.

Rosanne Barr's first Tonight Show appearance

"An Evening with Robin Williams"

 

I fell out of my chair at the theater when he hands the bag of shit to the lady at the dinner.

From the South Park movie: When Cartman pulls out the megaphone and said, "How would you like to suck my balls?" I had tears rolling down my face and was convulsing.

 

Various episodes of "Seinfeld," in particular "The Puffy Shirt" in season 5.
When I was in college, I loved Conan O'Brien's caricatures of Bill Clinton, Bob Dole, Mike Tyson and Don King.
Various parts of "Office Space," "Dumb and Dumber," "National Lampoon's Christmas Vacation" and the part in "Weekend at Bernie's" when Bernie falls out of the boat and is banging off the buoys.

 

Surprised "Caddyshack" hasn't been mentioned yet. Baby Ruth scene.

 

Underrated movies that kill me each time.

Top Secret!
UHF

I actually think Top Secret is funnier than Airplane and I love Airplane.

 

The Real World spoof on Chappelle Show.

 

Also, When Keeping It Real Goes Wrong.

I'll give some love to Friends, especially the episode where Phoebe and Chandler try to seduce each other.

"I'm really glad we're gonna have all the sex."

 

And the Rick James skit; when he was grinding his boots into the couch.

And YouTube's Drunk Baby.

And Tourette's Guy.

 

The scene in A Fish Called Wanda when Otto (Kevin Kline) is torturing Ken (Michael Palin).

 

Any Simpson's with Sideshow Bob or Rainier Wolfcastle.