Princess Debut. It's the most generic game when it comes to girly-ness. Lots of pink and curly UI, get to pick your outfits and your boyfriends as to who you will take with you to the ball. The music is good though and the graphics are well done for the system. I've played through this one more than I'd like to admit: It's…
OMG, Smackdown 2 on the PS2. Me and my buddies racked up almost 20 years of history on the co-op story mode. That was the best ever, it's a shame they went single player only on story mode after that.
seiken densetsu 3 is a sex. and yes super nintendo RPGs tend to be like "Uh what?" to some of my friend BUT THEY'RE THE BEST. Also Dwarf Fortress shouldn't be a guilty pleasure. It's a bad-ass game, and the new version has me more excited than any major commercial releases coming up.
Normally, when I like a game, it is because I believe it is deserving in some way. And I'm usually right. So though I say Pokemon Snap, I wasn't really embarrased by it. It wasn't really a guilty pleasure. The same is true of Hunter Hunted. That was a good game, which just had some thematic flaws and sub-par art. But then…
I'm going to go with Trespasser in its inital, unpatched state (not sure whether it ever got patched to any major degree. Probably not). It's broken in every way imaginable, but the fact that you're never entirely sure what's going to happen just makes the game more compelling. I'm pretty sure it's the only game ever made…