well, just any old lucas arts game should do. :)
by the way, if someone here speaks german, check out "die drei ??? und das gruene tentakel" (the three investigators and the green tentacle). it mixes game scenes from maniac mansion with clips from the "drei ???" audioplays, which are very popular in germany. it's really great!
http://www.tentakelvilla.de/download/sonstiges.html

Man.. crap... hmm.. I remember searching thru Youtube and I found some vids of a guy who did voice overs on old dos games.... dang it.. it's going to friggen bug me till I find it now.

I'm talking oolllld school like in the 2d Scroller types.

LucasArts games is an obvious choice. You can find a lot of similar funny stuff across puzzle/adventure genre: Discworld and Discworld 2 (dialog with Skazz is just too funny); The Incredible Machine and The Incredible Toons; Goblins (all three games); Space Quest (any of them); most Legend Entertainment early adventures (those are not that cinematic but with right approach you can get a few good outtakes); Rex Nebular (you can play on similarities to Space Quest). If you dig a little deeper you can find funny stuff in almost every game -- sometimes in a form of Easter Egg (Pacman level in Wolfenstein 3D), sometimes not completely intentional (badly overdone monsters -- just check bosses in the same Wolf3D), sometimes part of the game (radio communications in Wing Commander III).