Personally I find the Fable games some of the most hilarious. Also Brutal Legend is very funny. Deadly Premonition is too full of entertaining moments.
This. Off the top of my head, I think Persona 4 is pretty funny too.
Speaking of Persona, what I played of Persona 3 Portable also struck me as pretty funny and weird in a really, really good sort of way. Not always laugh out loud funny, but more of a "this is nuts but I love it" kind of grin.
Saints Row: The Third is genuinely funny in its ridiculousness. Fable games are brilliantly funny in their dialogue ("Get your miscellaneous items here!") Grand Theft Auto IV even had its moments even though it was often serious. All of the Max Payne games were funny in their macabre dark humor. Portal 1&2 are also notoriously funny and clever.
The original is also hilarious. I should also add Conker's Bad Fur Day. Those might be the only three games that sought to make me laugh, and succeeded.
Saints Row the Third is genuinely hilarious with how utterly absurd and self-aware it is. Portal and Portal 2 also obviously deserve mention, as does Conker's BFD.
In terms of over the top absurdity, I'd say Alpha Protocol and Saints Row 3 are pretty damn funny. For just zany whackiness, Deadly Premonition (of course), God Hand, and I'd say Shadows of the Damned too, despite how genuinely disturbing it is.
The Portal games, Anachronox had some pretty funny bits, Monkey Island 1 and 2, the Uncharted games had some good lines, the Mario RPGs have good lines too, the You Don't Know Jack games, and the Telltale games usually have good lines in them.
EDIT:
Oh shit, Saints Row the Third had a ton of good lines.
Maybe not what it was going for, and all humour is subjective anyway, but man, I laughed hysterically throughout too many parts of that game.
Apart from that, most of 'em have been mentioned, Portal and Psychonauts and etc. And yes, Comic Jumper is genuinely funny, even if the gameplay is kinds junk.
I have been playing quite a few adventure games recently and I legitimately found myself laughing quite a lot at numerous points during Deponia and (to a lesser extent), Harvey's New Eyes. Both good games; Deponia has goofy, sarcastic humour whereas Harvey is dark black humour (lots of contrasts between sweet innocent girl and horror themes).
Psychonauts, Sam & Max (especially season 3). The Bard's Tale from inXile is also quite hilarious in my opinion - too bad that game's fucked by its voice acting.
While I wouldnt call these games comedys i've had a laugh playing them.
Fallout series
Metal Gear Solid series
Dead Rising series
Yakuza series
Comic Jumper had some funny moments but the game is a chore to play through. I also enjoyed Shadows of the Damned although I know Suda's humour can be alittle too dumb and tasteless for a lot of people. Also Catherine but i'm guessing you already know that.
Psychonauts for sure. Not only is it genuinely funny, but it is also dark and depressing as hell at times. So both sides of the spectrum is presented quite well. Damn, Milla's repressed memories... The way they managed to make such a fun game on the surface, with so much pain and misery hidden beneath, shows how awesome Double Fine really is.
I guess I can't really bring much new to the conversation. Portal 1 and 2, Persona 3 and 4 and most every BioWare game all have some pretty hilarious parts, although Portal 2 probably takes the cake, no pun intended.
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