Paper Mario: The Thousand Year Door.
Conkers Bad Fur Day comes to mind. I can't think of any other titles really that match it. My friends and I have always enjoyend unintentional comedy from various racing games :^)
"Let justice be done though the heavens fall." - Jim Garrison
"Ask not your horse, if ye should ride into battle" - myself
Grim Fandango and Broken Sword were probably the only games that made me laugh every 2 minutes. Superb scripts and top-notch voice-acting!
N-Portugal.com - A Portuguese gaming site. Check the latest N-ews! 
Portal, Conker, Psychonauts, GTAIII (particularly the commercials), Postal, any of the old LucasArts adventure games, all hilarious in their own way.
To pick one specific element that was funniest to me would have to be the GTAIII c ommercials, the GLaDOS battle in Portal, or The Milkman Conspiracy level in Psychonauts. All three had me in tears I was laughing so hard.

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