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.
The Stanley Parable, although it couldn't be further from High on Life in terms of its comedy. Personally I don't love the game but it's absolutely hilarious.
I tried the game and it really wasn’t a fun experience for me. It’s just an overpriced walking simulator with some not really funny dialog playing.
All I did was trying to find bugs because I wanted to uninstall after 30 mins, when I figured out it's not just the start that is slow, it’s the entire "game"
Its a bit extreme, but crack-life for half-life. You know there are some people saying they get brain rot from memes? This is like the bottom of a sinkhole for your iq. Every sound is some random effect, the wortigons have afros, the headcrabs are British, your hud is in webdings, the soldiers speak in old tts and the smg has infinite fast firing grenade launcher.
Is a lot, and while you are lost in a word where nothing makes sense, you are losing your ass off. If that's isn't enough, there's a standalone mod, that's even stupider, even bigger, even more bizarre.
But it's probably not for everyone, its very 2000 edgy humor, so if it's not your thing, don't force yourself with it (might wanna check some vids, Jolly has a good ones, but i think he deleted it some time ago).
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.
When it comes to "classic" comedy, then Hi-Fi Rush is one of the highlights in recent times. Not only are there a lot of jokes in the dialogue that landed for me, all the cutscenes are also loaded with perfectly timed visual gags. Lots of humour hidden in the environment as well.
Other than that, any "serious" game that has a wonky physics engine can accidentally be pretty funny on accident. Slinging around corpses in Dark Souls 1 for example.