Full throttle, that was a great one as well.
Bit more mature with the whole biker theme, just a pity it didn't go the whole "hog" with you shifting crystal meth. What about and a sub game where you beat on mods from your hog?

The ultimate for me; Leisure Suit Larry.
I mean that's keeping it real, an adventure about an unattractive man trying to get laid with comical results.
I can relate to that.
Someone needs to make another one I can really relate to about a stoner on a quest for decent weed and every time he tries to score he gets shafted. having to "use" butane "with" mold weed to get by till he finally reaches endgame and gets a nice stash of high-grade.

Highly recommend the new adventure releases from Telltale games.
You mentioned Sam & Max, the original and the new ones are still some of the wackiest fun I've had with my trousers on imo(totally hilarious).
New Monkey Island as mentioned is being really well expanded on by them as well.