my personal funnystuff list:

Plays: The Actor's Nightmare, Sister Mary Ignatius Explains it All. Christopher Durang. Travesties, Tom Stoppard (if you can understand what's going on; requires prior knowledge of Stalin, James Joyce, Ulysses, The Importantce of Being Ernest, cuckoo clocks ..) funny at times, heartwrenching at others: Arcadia, Rosencrantz and Guildenstern are Dead, Tom Stoppard.
Books: Good Omens, Terry Pratchett and Neil Gaiman Betcha Can't Read Just One, Alan Dean Foster The Decameron, Boccaccio parts of The Master and Margarita, Bulgakov, if taken at face value, are hilarious most Thurber any Ogden Nash any Edward Gorey HHGttG (which can also go under plays and movies)
Movies: Marx Brothers Dr. Strangelove (If you don't get the President on the phone, you'll have to answer to the Coca-Cola company!) Plan 9 from Outer Space Spinal Tap Rocky Horror Picture Show with the following conditions:first viewing as highschool student with friends, all in silly costumes, Harvard Square, midnight, one time only. Them!, It Came from Beneath The Sea, Dr. Cyclops, Mothra, The Beast from 20,000 Fathoms, any other 50's-ish scifi movie that involves giant radioactivity-induced monsters
music: Tom Lehrer songbook: Joe's Got a Head Like a Ping-Pong Ball, collection of parodies (title tune: William Tell Overture)
computer-related: /usr/bin/fortune the Jargon files (http://jargon.org?) the BOFH
comics: www.userfriendly.org www.nitrozac.com www.sluggy.com Doonesbury

Chocolate Pi (giggling at what an odd assortment of things makes her laugh)