Later that year, my dad got a 486/33 Compaq, and I was ecstatic. In addition to happening upon the brilliance of Sam & Max Hit the Road - unaware they were also made by Lucasarts - I tracked down Monkey Island 2 a few months later to much elation.
I was actually a little bit disappointed in it.
I'm not exactly sure why, to be honest. I remember I was distraught and confused over the ending, and some recent googling around has shown me that I wasn't alone. I also didn't think it was quite as funny, which I sort of agree with, but I think Monkey Island 2 is a much better game overall. I think, line for line, the original game might have some slightly better dialogue. And most of the interesting characters from Monkey Island 2 were carryovers from the previous games (Stan, the Men of Low Moral Fiber, the Voodoo Lady, etc.) Wally only became retroactively interesting after his appear in Curse of Monkey Island, and Largo isn't so much funny as a plain old jerk.
I do like the situational humor a lot more, like the general silliness of the costume party or the whole Governor Phatt (fat lol) thing. The game in general is much brighter, with more varied locales, and feels less claustrophobic than the original. A lot of the atmosphere is also conveyed with the amazing soundtrack. The first Monkey Island game had some great music, but it was sparse, and huge chunks of it are played in silence. Monkey Island 2 was the first game that used the iMUSE system, which perfectly transitions the music from screen to screen. Every screen in Woodtick village has a unique melody, each of which exemplifies its inhabitants but the town in general. I've been humming the various themes for the past week, much to the annoyance of everyone around me.
I still don't think it's quite as funny - one of my favorite parts of the first game was barging into Meathook's house and senselessly mocking him for no great reason. I also loved the insult swordfights, although not so much anymore. I've appreciated some other jokes more though - for some reason, the idea that the Monkey Island inhabitants communicates passive aggressively through a series of notes is oddly funny now, though I didn't quite get it back then.
People's sense of humor (and perceptions in general) tends to change over time. Upon my recent playthrough, I liked Space Quest V a lot more now than I did when I was younger, which I also had felt paled to its predecessor. Of course, this is one of the big reasons I've been replaying all of these old adventure games from my youth. Revisiting old media can be preyty dangerous, considering a lot of the cartoons and movies I loved as a child don't quite hold up (with occasional exception of something like The Goonies), but I'm actually finding new appreciation in my (somewhat) older age, rather than disdain.
I'd be lying if I said that nostalgia didn't play a part in this, though. Our first online service was Prodigy, and I got hooked on the message boards, where I joined The Monkey Island Fan Club and posted under the name Muad'dib, having just seen the Dune movie. We actually got together to design a theoretical Monkey Island 3, since the previous game ended on a (sorta) cliffhanger and Curse wasn't coming for at least four more years. I'm sure they're lost now, but I wish I could dig up those old text files. They were probably awful, much like anything you would do when you're thirteen, but it would've been cool to see how it compared to the real sequel.