My contribution:
George Micheal: Father Figure - 1988
If you're not a bit embarrassed, you're doing it wrong.
Oh boy. This could be all Fall Out Boy songs, so let's move on. It's not like I listen to a lot of guilty pleasure music or anything. EDIT: Damnit, this lags every page that it's on.
This is definitely my favourite Fall out Boy Song:
Ooh nice, but I see two bands here I'm not ashamed to rock to. Screw the haters.
( ^^ I don't care if the original is a significantly better song, this one's still the one on my playlist.) Like other people, I could go on.
I used to be fairly 'guilty' about loving a Cher song so much but.... fuck it, the shoop shoop song is all kinds of awesome.
I've got one for saturday nights: It's actually just some pretty good music if you didnt know who was rapping - that's Andy Hartpence (NOA_ANDY), the former head admin of the now-defunct NSider forums (that was the official forums on Nintendo's website), the first internet site i spent a significant chunk of my life on. Place was gigantic. Actually... i can't decide if that makes it embarrasing or awesome. "It's Saturday Night Ha-le-lu-lu-lu-ja-ja!"