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.

Just recently played A Hat in Time. We're never told, but every detail points at this being the fantasy adventures of a little girl with A LOT in common with Calvin from Calvin and Hobbes, an overabundance of imagination and hyperactivity. Charming and funny (well, save for Queen Vanessa, which I feel was instead a masterpiece in ambience). Loved it, gotta try the DLC. Just be ready for hard platforming at many places.

Improbable Island

Ace Attorney has some really hilarious moments throughout the series.

Similarly, Ghost Trick, although it's been years since I've played it.

Yeah imma a just gonna say it.

Borderlands 2 esp the Mr Torgue DLC. The DLC is a slog, but Torgue had me losing my shit throughout it.

Probably Minecraft with my 5 year old. Yesterday and today. Been loving it.

Can't say which one is the funniest (probably jazzpunk), but here are some that I found funny:

• Jazz Punk
• Procession to Cavalry
• Thousand Arms
• Metal Wolf Chaos
• Frog Fractions
• Monkey Island

Maize. I had no expectations going into that game except what the brief Steam summary gave me, and I was not disappointed.

Bucket Detective. This was recommended to me by someone who said "this is the weirdest game you'll ever play", and I think they were right.

I wish I could forget all about Day of the Tentacle, so I could play it all over again and rediscover everything.

That whole ordeal with Red Dead Uncle Fred is hilarious, especially after IRS arrests him and restrains him with literal red tape.

Fashion Police Squad

Not the funniest I have played, but I definitely found it funny and fun.

Someone else mentioned Procession to Calvary - an adventure game set in a cut and paste world of renaissance art with a very surreal plot and sense of humour. Pythonesque.

There Is No Game is pretty hilarious, the voice acting always makes me crack up.

Agatha Knife is a funny point and click adventure game where you're a 7 year old girl who's a butcher and needs to set up her own religion sacrificing pigs in the basement for... Reasons.

It's not a very good game, but I laughed my ass off through the Deadpool game. The one that immediately comes to mind though is Bulletstorm. It definitely set the bar for high-brow, sophisticated humor.It's a shame that People Can Fly chose to go with Outriders, because I'd kill for Bulletstorm 2.

Anachronox

The Dungeon of Naheulbeuk: The Amulet of Chaos is hilarious and fun rpg