Portal and Portal 2 are natural follow-ups to Stanley Parable if you haven't played them yet.
I also found the bone dry and character driven humor of Tactical Breach Wizards to be very entertaining, on top of it being an incredible game mechanically as well. 10/10.
If you're okay with very casual games, give Thank Goodness You're Here a try (and it's apparently on sale currently)
The classic Lucas Arts adventures. Monkey Island, Day of the Tentacle, Sam & Max, Grim Fandango.
Turnip boy commits tax evasion was a surprisingly sweet chuckle the whole way through.
Esoteric Ebb is a d&d narrative RPG in the mould of Disco Elysium. It has sharp writing and parodies d&d tropes in some unexpected ways.
High on Life is pretty good. Didnt get far into the sequel.
The funniest parts happen early on in the game too, imo it peaks when you collect the knife, so if it doesnt interest you by then with gameplay or humour its safe to drop it early.
I’ll echo what some others said about Portal, but here’s a handful of games that I’ve enjoyed for their comedic value:
What the Golf is pretty funny if you like/hate mini golf.
Many of the LEGO games have some good humor: Star Wars is my favorite, but LEGO City Undercover was fantastic, too.
Borderlands 2 has some great comedy, with The Pre-Sequel as a decent runner up.
The Yakuza games are fantastic; I recommend Yakuza Kiwami for a low-cost entry that allows you to dip your toes in and get the feel for it
Untitled Goose Game is funny because you make it funny.
Never has a game made me laugh out loud like when I first discovered it. Clever humour, unique characters, and each line of dialogue is packed with effortless charm and wit. Not to mention the philosophical themes disguised as one man's quirky Day of the Dead -themed quest to get to the afterlife.
The puzzles are a product of its time so a walkthrough might be needed. But that's forgivable for the game's big picture.
Wish I could wipe my memory of it and play it all over again.
The original psychonauts had me laughing all the way through, the sequel is also very charming tho it felt a little darker.
I really enjoyed the slapstick of jazzpunk. If that is your kind of humor.
Portal 2, Stephen Merchant provides most of the humor with his voice acting for Wheatley.
Undertale* is a classic and must-play.
*might also make you cry
Goat Simulator 3 is silly ridiculous. If you want to not think and just laugh at stupid/funny shenanigans, this would do it.
I was rather charmed by the humour of Tactical Breach Wizards.
The Dungeon Of Naheulbeuk: The Amulet Of Chaos was hilarious. The dialogue is just fantastic let alone all the little details that you may (or may not) catch.
You should give Full Throttle a go if you like point and click adventure games.
Slayers X is a hilarious boomer shooter
South park - the stick of truth is pretty good if you like south park.
Battleblock Theater is really funny in like a slap stick and kind of juvenile kind of way.
No One Lives Forever is a spoof of Austin Powers, if that gives any idea of the humour level
I Am Bread is amazing.
Pizza Tower is pretty great. Every frame of that game is a hilarious work of art.
Just finished Tales from the Borderlands and I laugh a lot so there you go
Journey To The Savage Planet has some decent giggles
I was wheezing at Dream Daddy. Probably the most I've ever laughed when playing a game.
Terry Pratchett's DiscWorld
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