While there are a few gems I'd call funny (Monkey Island for example), I'd say the Portal games are probably the only ones that had me laughing out loud.
the wario ware games always made me genuinely laugh.
There was a bit in dragon quest 7 about 20 hours in when some guy on an island drops the F bomb (or maybe it was just '****') but it came right out of leftfield and there had been no swearing prior to it. that really made me chuckle at the time.
There was a PS1 wrestling game where you could headbutt the opposition in the nuts. Every time you did it, it would make a comical "ding ding" sound effect. Over use made it funny for everybody but the recipient.
Also, that rapping fighting game where you could be members of Public Enema. Def Jam? Anyway, if you played Flava Flav, you could make him go "Yeeeeeaaaaaaah boooooiiii!", which again, was funny due to over use.
I think when my friends and I break games it's inadvertently funny. I miss the halcyon days of launch 360 where we'd play hide 'n' Seek and Take the Tower in CoD2.
I was really chuckling the other day on Dead Island when some people joined my game, we drove off in a truck and they managed to get it wedged between a tree and a coach with millimetres spare either side, so we had a real Austin Powers moment where he was shunting for ages to get it unwedged. (you had to be there...)
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