SAM & MAX HIT THE ROAD / LucasArts / PC
While Steve Purcell was working as an artist and animator for LucasArts, he was also publishing a cult-hit underground comic starring a psychotic rabbit and a canine shamus. Around 1989 or so, somebody in the Top Brass at LucasArts apparently decided that these two great tastes would go great together, and work on the first Sam And Max game got underway.
The game wouldn't actually see the light of day until 1993, however, but it was well served by the delay. Aside from the move to VGA graphics and the more colorful and fluid style it allowed, LucasArts also had four years of experience making other very solid adventure games to draw on. The end result is arguably their best adventure game ever (I'd personally argue for Monkey Island 2, but this is a very close second).
Now, there is no form of humor that I find more obnoxious than the running snark-fest (example #1 being the TV show Scrubs, which I really wish would just disappear from the Earth in a giant ball of fire.) Unfortunately, Sam and Max and their dialouge in this game are exactly that. Yet, somehow, they manage to be funny more often than not - I attribute this to the surreal world they inhabit and the constant injection of the absurd into the formula. If Sam and Max were wandering around in Real Life doing this routine it would get incredibly grating incredibly quickly, but in this Looney Tunes-esque caricature world it manages to function well. Sam and Max's repartee still falls flat sometimes and you wish they'd just stop trying so hard, but when it works it is genuinely funny.
That's the main reason you play, but the game itself is really well-designed as well. As an adventure, it's just challenging enough without being maddeningly obtuse, and the simplified interface works out well. It can still be accused of being a little too easy, but in a game where the main point is to just enjoy the ride, that's OK. The adventure team responsible for so many early LucasArts hits is in their best form here, with really nice graphics and an excellent dynamic soundtrack employing the iMuse system of shifting cues as you move about.
* Gameplay Demo