For me it's probably Jazzpunk, but I liked Disco Elysium too. I've been looking for something to scratch that "Jazzpunk surrealist comedy itch" for a while and not many games have come even close.
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.
@JCPhoenix They definitely do! I replayed Sam & Max and DOTT on an emulator for my phone and played the remastered versions of Monkey Island. They are still awesome games.
I want to add "ToonStruck" to this list as well. One of the funniest, weirdest games I ever played.
Yes! Sam and Max is wonderful! There's something so perfect in the way they react with complete nonchalance to all the weird stuff going on. And the soundtrack is great too.