I was thinking about playing High on Life shortly after the release but I’ve seen a few reviews that depict the game (or maybe just the jokes) as so-so.
I think Portal 2 is probably one of my favorite games that has a lot of humor at it’s core. But I can’t say I’ve played a ton of games where that is a front-and-centre core element. I know there are some cult classics out there that I haven’t gotten around to playing yet like Conker’s Bad Fur Day and Psychonauts.
It also doesn’t need to be an entire game. The Hotline Miami 2 workshop content GARFIELD CAMPAIGN made me laugh.
Edit: Bonus points/extra challenge if it’s not on PC. While I do game almost exclusively on PC I would be curious to hear what’s out there for handhelds like GBC, PS Vita, 3DS, PS2, PSX, and so on.
Going back to legacy PC games from the 90s…
For adults that don’t mind blood, guts and cursing: Redneck Rampage
Something much more innocent for kids though: Mystic Towers