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.
There is a mod made for Halo: Custom Edition called “Cursed Halo”. The creator, Inferno Plus, has made three versions, now, and the newest is for Halo: Master Chief Collection. The humour is abundant, and it is an absolute ride when he makes a new version.
Oh, something I thought of, there is a ROM Hack for Super Mario World I’d recommend, too, called “Diagonal Mario 2”. Being in that community, I know of several fun, funny, and trolly hacks- but Diagonal really doesn’t rely on SMW, kaizo, or community knowledge. Its humour and gameplay are pretty accessible for anyone.