The Stanley Parable was pretty funny
Gaming
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I think it'd have to be Portal...mmm, the first one. I think learning about Glados the first time is a little better than the whole potato thing.
For a game that's a full comedy romp, West of Loathing consistently ruined me with laughter. The spittoon descriptions are probably the most derangedly funny writing ever put into the world. I've got to remember to play the sequel one of these days. Its also extremely mechanically satisfying, with several enticing roleplaying moments (as well as the occasional dramatic or scary moment that hits just as well as the comedy)
For a game that's not explicitly only comedy but still hits strong marks, Yakuza 0 is a full meal. While most Yak games are fairly wacky when it comes to sidequesting (1 being perphaps the single exception, as the beginning of the series was quite dry), 0 feels like the one where they really hit their stride. There's so many flat out ridiculous moments (you've most likely seen the chicken, and that's just one of many) that you even forget this is also a heavily dramatic story and a full blown action beat'em up.
If you liked that it's based on a browser game called Kingdom of Loathing, the gameplay is not as tight or refined but there's plenty to do and it's pretty enjoyable to play when you have some time to kill on a work pc lol.
Disco Elysium. It’s much more than funny, but it can also be really funny. Cuno is really funny.
Came here to say this; just wanted to add that it was simultaneously the saddest game I'd ever played.
It's both the saddest game I've ever played and perhaps the most uplifting one. It balances the knife's edge between nihilism and hope so well. It can also be hysterically funny, yes. It's truly unique in terms of writing.
I'd recommend Sam and Max Hit the Road. It's older, and its sense of humor is a bit out there, but if you "get it" it's great.
So many of those old adventure games were hilarious. The Monkey Island series, Day of the Tentacle, Leisure Suit Larry, Space Quest. But I was also a kid back then (probably shouldn't have been playing Leisure Suit Larry...). I wonder if they'd still hold up for me today.
I'll add the Discworld games. And Simon the Sorcerer!
Monkey Island
Only game I ever lol’d at was Psychonauts.
Both of the Psychonauts games had such great writing, comedy is best when interwoven with actual substance and they nailed it
I find the lack of Space Quest titles in this thread unsettling. For me, it's Space Quest IV, but they are all absolute gems.
I prefer Leisure Suit Larry, but I'll upzipper any Sierra game!
It's really hard to top Jazzpunk...
I know right? it's so great I reinstall it every few months just to experience it again. It never really gets old
No One Lives Forever though it's ancient now. I remember sneaking around just to listen to the bad guys talking to each other.
One game series that is not known for being especially humorous actually can be: The Halo games. More specifically the enemy grunts. If you sneak up on them and listen to their dialogue, their mix of faux bravado, cowardice and delusion of grandeur can be really funny. Especially because Master Chief is “The Demon” to them. A near-mythical monster. Just choosing the right time to reveal your presence to the grunts can result in comedy gold.
Outer Worlds has a great sense of humor.
The game I've laughed the most while playing is Jackbox. Fibbage and Quiplash have me in stitches every time, although it depends on how funny your friends are.
I almost can’t believe the lack of Strong Bad’s Cool Game for Attractive People in this thread.
"Mr. Evrart is helping me find my gun" is the funniest interaction in any video game I have ever played by an order of magnitude
Stanley Parable and Trover Saves the Universe are both pretty funny. I'm sure there are a ton of really funny games, but for some reason, they're not coming to mind.
For me its gotta be Donut County. I was baked out of my mind and my best friend was like "Dude you gotta play this game" and handed me his controller. It was awesome.
South Park: Stick of Truth and The Fractured But Whole I'd guess people either hate it or laugh their way through it.
Dongeon Keeper 2 for me. Killing scared heroes was really fun.
I like LEGO games for their simple light-hearted humor and recreation of well known scenes from other IPs, esp. SW\LOTR ones.
Ultimate Chicken Horse might be one of the top party games for getting a laugh for me. It's always fun to see someone hyperfocused to make a jump, only to get hit by an arrow, followed by a wrecking ball hitting them into a sawblade.
Conker's Bad Fur Day.
First off, Rare had a reputation for good games, but they were cute, child friendly games. Conker was even a cute character with child friendly games. Then they made this... thing, which starts with Conker hungover from a night drinking and quickly descends into him fighting a giant poo monster. The game was rated R/18, which was crazy for Nintendo. The amount of little movie references everywhere was insane, also.
Either Jazzpunk or Octodad: Dadliest Catch
Both had me laughing so hard I had tears in my eyes at various points.
Tiny Tina's Wonderlands if you're into Borderlands-style games (shoot and loot). I'm not, but for the 45 minutes that I played, I laughed quite a bit.
And of course The Stanley Parable.
Some coop games, like Battleblock Theater or Magicka, were definitely the most funny for me, with all the dumb stuff you can do, fuck with your friends, etc. but those depend on the people you play with. With friends, every game can become super funny though, even more serious stuff.
As for single player, the ones I remember the most were Donut County and maybe the Frog Detective games, those had some really funny moments and writing.
Definitely Grim Fandango. First game to make me laugh out loud, personally it's clever and witty, and I love it to bits.
https://store.steampowered.com/app/316790/Grim_Fandango_Remastered/
Hatoful Boyfriend has some really great moments, especially if you pursue Anghel or Okosan. It also will make you cry your eyes out in the true ending, so there's a good balance.
Showing my age here but Deer Avenger was pretty damn funny:
https://en.wikipedia.org/wiki/Deer_Avenger_(1998_video_game)
Any shovelware with lots of bugs, continuity errors, and English language fails. I’m the type of person who believes in “so bad, it’s good” (or at least so bad, it’s funny). Warning for TVTropes link.
The Precession To Calvery was hilarious from beginning to end.
I also love the humor in Portal 1 and 2.
Frog detective is also super cute and funny.
Not single player/story funny, but I don't think I've absolutely lost it to any game (possibly even any thing) more than Gang Beasts. Get 8 friends together for a rumble and cry laughs will be had.
One time back when we were living in an apartment with an inward courtyard facing window, my wife and I were laughing so hard a neighbour threw something at our window to get our attention so they could shout at us to keep it down. It was only 10pm on a Saturday :/