There was some talk of “Billy don’t be a hero” I can stand that song because of a version done by an Australian band, the Doug Anthony All Stars, “As Billy started to go, they said ‘where did billy’s head gooooo’”. Juvenile, but funny.
Also, I can’t beleive no-one has mentioned Michael Bolton, c’mon, tell me you don’t cringe every time you hear “How am i supposed to live without you”. Or Def Leppard’s “When Love And Hate Collide”, or “Push the little daisies” by ween. But i gotta say the new romantics take the cake with this sorta stuff, “Do you really want to hurt me” by culture club, “Hungry like the wolf” and “girls on film” by Duran Duran and Human League “Don’t you want me”. OK, personal purging over. 
I just wanted to comment you on using the word ‘smarmy’. It’s not used nearly enough.
Actually, I cringe when I hear ANY Michael Bolton song, particularly his grammy-winning slaughtering of “When a Man Loves a Woman”. “Do You Really Want to Hurt Me” actually would be a decent song if it were done by someone other than Culture Club, a group that was trying for a faux-reggae sound with that. Perhaps a real reggae group could have done it justice.
yes!
Speaking of smarmy, what about:
“Feelings” by Morris Albert?
“Having My Baby” by Paul Anka?
“You Light Up My Life” by Debbie Boone?
Of course, Michael Bolton is hands-down the Winner Of The Smarmiest Singer Award…