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Looking for books that make you laugh out loud? Here's my list, grouped into fantasy, scifi, and just plain funny ("Real world"). Also check out my "Fun" list, because it's a really fuzzy line between these two - basically it comes down to these ones being really funny, while the "fun" books are just pretty funny (a distinction that may sometimes have more to do with my mood than anything).
Fantasy:
Terry Pratchett's Diskworld books
Bored of the Rings
Robert Rankin
To be honest, I'm not entirely sure how to classify Rankin. I wouldn't, myself, be inclined to classify him as fantasy, but bookstores and libraries tend to, so ... Rankin's world is recognizably the real world, although not as we know it. There's lots of them (and the titles alone are pretty funny, like The Hollow Chocolate Bunnies of the Apocalypse), but for some reason my favorites (and those of my teenage son) are those about that famous private investigator, Lazlo Woodbine (and of course his faithful Guardian Sprout, Barry):
Waiting for Godalming
The Dance of the Voodoo Handbag
William Goldman
The Princess Bride
Craig Shaw Gardner
The Ballad of Wuntvor
A Difficulty with Dwarves
An Excess of Enchantments
A Disagreement with Death
Science fiction:
The Hitch-hikers Guide to the Galaxy
John M. Ford
How Much for Just the Planet?
This is a Star Trek book, and I doubt it would be funny to non-Star Trek fans. But for those who are (well, not if you take Star Trek deadly seriously!), this is hilarious. Don't worry, it's not a spoof, and it's not funny because it's so badly written or anything. No, this is a class act. It's just ... a very funny situation, and very humorously written. I love it.
Spider Robinson
has written lots of very good science fiction books, not necessarily amusing. In this series, however, he goes to town on puns. Basically each book is a series of short stories, the unifying factor being that they all take place at Callahan's bar.
Callahan's Crosstime Saloon
Time Travellers Strictly Cash
Callahan's Secret
Real-world:
Three Men in a Boat
Dave Barry
Oh, where can I begin? I just adore this guy, and so does my teenage son. He's a humor columnist for the Miami Herald (although his work is widely syndicated so you might read it anywhere). Most of his books are collections of his humor columns, which are great, but my absolute favorites tend to be ones that aren't:
The Only Travel Guide You'll Ever Need
Dave Barry Slept Here: A Sort of History of the United States
Dave Barry Hits Below the Beltway
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