Enrique Iglesias - "Escape"

Nowadays Enrique has been busy teaming up with Pitbull, but back in 2001 he was still riding the "Latin Explosion" wave.  With the likes of Christina Aguilera, Jennifer Lopez, and Ricky Martin, Enrique (and his mole--RIP) made a name for himself launching several hit songs including "Escape".

Rupert Holmes - "Escape (The Pina Colada Song")"

Few songs make me as angry as this song.  No, it's not because the dude placed a classified ad after growing bored with his wife.  It's also not because the guy who sang it was named "Rupert"--that's actually a pretty cool name.  This song is just one of those select songs that immediately triggers the nails-on-chalkboard feeling.  Forget waterboarding, play this song instead.