Hi. I'm the guy who played Monkey Island 1 as his first PC game ever in '92, and didnt touch another point adventure game until Monkey Island 2 in 2009~ish (remaster) and then again in 2019 when I got the retro fever.
The Lucas Arts catalogue is pretty solid. Recently I've played from Fate of Atlantis all the way thru to The Curse of Monkey Island . I do plan on playing the early ones like Maniac Mansion and Loom (and the other Indiana Jones one).
For me, Day of the Tentacle held up the most in terms of fun, Sam n Max was overall fine but let down by the ending and a few too many weird as hell puzzles. The Dig was absolutely stunning with its art and music, I honestly felt like this was the only game that was the one that I was most addicted to. Full Throttle was also good but I didn't really like the biker fighting. Still dunno what to do, honestly. Monkey Island 1 holds a place with me and I play this far too much that I think I'm going to wear it out. Monkey Island 2 feels like it drags on a bit and let's not get started on THAT ending. I can imagine if we had a real trilogy by the OG devs, it would make some sense and redeem itsself but thats not gonna happen. Fate of Atlantis felt like a real adventure and the last "level" was really fun. I rate Curse of Monkey Island pretty highly, better than Monkey Island 2 imo.
For me, I put Sam n Max alongside Monkey Island 2 down the bottom and then Day of the Tentacle and The Dig at the top. But this doesn't mean Sam n Max/Monkey Island 2 are BAD. They are still good and worth playing. Many enjoyable bits, some good gags but like I said, their endings leave a lot to be desired...
I hear great things about LOOM and Maniac Mansion. I will play them in the next few months I'm sure.