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.