Nexomon: Extinction cracked me up pretty much throughout the entire game.
Gaming
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Disco Elysium is the most recent game that was just chock full of humor, though maybe not focused on it specifically... beyond that the only games I can even really think of that had a focus on comedy were the old LucasArts classics. Sam & Max, Full Throttle, Monkey Island... And Borderlands.
I was just thinking about how this doesn't seem to be a thing anymore. Where are the comedic oriented games? Why is everything so damn dark, and serious and brooding nowadays?
But I haven't played that Not-Really-Rick-and-Morty-shooter. I heard that was funny.
Whiplash back on PS2
The MLB Slugfest series. I don't even like baseball, but they'd sneak these one liners into regular commentary and it just killed me.
"Everyone that came out to the ballpark today is getting a free piece of sandpaper"
Well that cheesy Deadpool game.