79. Britney Spears

Again, sometime it isn’t just the song; it is the person singing it.  This is the case here, with Britney Spears who may surprise people by only entering this list once.  We don’t have a problem with modern day Spears.  After her era of Kevin Federline, head shaving and overeating, Miss Spears escaped the status of a high round dead pool draft pick to become a slutty dance siren who has regained her looks.  Sure, her songs have the substance of popcorn farts, but she is not extending beyond what she is….like she did when she tried to act in 2001.

Many singers have translated into great actors and others are Madonna.  She may not have stunk up the silver screen like the Material Girl, but it was Golden Raspberry worthy.  The main song of the film was a song of pubescent angst of being at the “Crossroads” of life.  Problem is a song like this can’t have any real shelf life, as once you are in your 20’s (which she was already at the time), could there be any real doubt as to whether you a woman or not?  Lyrically the song is light years over many of the other crap on this list, but having the song crooned by someone who factiously extended her virginity by years, skanked it up as jailbait in videos and claimed she’s “not that innocent” just made this song completely fraudulent.  Besides, who wants to see Britney sing an introspective ballad anyway?