Kourtney Kardashian

20. Kourtney Kardashian

The "Two Girls Makin' it Big in the City" storyline is hard to invest in when those two girls are already outrageously wealthy and successful, and when both appear on this infallible document proving their ill-repute.

Lindsay Lohan

19. Lindsay Lohan

It's always hard to watch the fall of someone who may, for a time in their professional careers, have held genuine talent and promise. Lindsay Lohan's now probably never going to achieve what she could have, but that's what happens when you decide not to capitalist on a starring role in Herbie: Fully Loaded.

Kris Jenner

18. Kris Jenner

Because it just wouldn't make sense to do this if we're not going to aknowledge the woman who started it all, for better or worse (worse. Definitely worse)

Charlie Sheen

17. Charlie Sheen

Even when Charlie Sheen was inhaling coke for hours every day and locking call girls up in his motel rooms, there was a certain naive, endearing quality to him you couldn't help but appreciate, until he figure that out and got a twitter account.

Jon Gosselin

16. Jon Gosselin

A running theme so far in this list is people who probably aren't as famous or as rich as they should be. Jon Gosselin arrives in at number 16 to ease our fears, since he is neither rich or famous anymore.