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The 54 Worst Celebrity Trainwrecks, Ever

9:48 AM
You’ve seen hot celebrities, you’ve seen careless (but entertaining) celebrities, now it’s time for the worst celebrity trainwrecks, ever.

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How much damage can money and fame do to people? We get a fair idea of it every day with our regular celebrity gossip, but to get a clear picture of how f-ked up celebrities really are, we went ahead dug up the dirt (it wasn’t that hard, trust us) on some of the most popular screwups in pop culture.

Before we start – this is a list, not a ranking – so don’t be surprised if one of the strangest celebrities of all-time comes in at #51, or why Britney Spears isn’t #1 (surprisingly, she’s not the worst of the bunch, but that’s a different story). Click on the celebrity’s name to get their ‘rap sheet’.

The “Will They Ever Learn?” Trainwrecks

Michelle Rodriguez

Hats off to this bunch – if you’re ever short of celebrity trainwrecks and need a reminder, rest assured that someone from this list will be in the news, helping some celeb gossip blogger make money off their sorry lives and reminding you that money and fame is not all that it’s cracked up to be.

1. Pete Doherty
Amy Winehouse
Britney Spears
Lindsay Lohan
Paris Hilton
Kirsten Dunst
Mischa Barton
Michelle Rodriguez
Kiefer Sutherland
Kate Moss
Naomi Campbell
Sienna Miller

The “Golden Oldies”

Tom ruise

You’d figure that with enough time, any trainwreck would learn the error of their misguided ways and try to fix themselves. Not this bunch.

The next ten celebrities are proof that time does not heal – and in the case of a few, it just makes things worse.

13. Sean Young
Daniel Baldwin
Mel Gibson
Heidi Fleiss
Tom Cruise
Paula Abdul
David Hasselhoff
Keith Richards
Sharon Stone
Roseanne Barr

The “We Never Saw Them Coming” Trainwrecks

Jessica Sierra

Celebrities who surprised us with their ability to mix with the best trainwrecks on this list. Sure, hindsight is 20/20, but these are the ones no one saw coming.

23.Eva Mendes

24.Owen Wilson

25. Lily Allen

26. Vanessa Hudgens

27. Jenna Jameson

28. Isaiah Washington

29. Jamie Lynn Spears

30. Katie Rees

31. Jessica Sierra

32. Brooke Hogan

33. Mary Kate Olsen

The “Media Whores”

Jesse Metcalf

Celebrities who, for some reason or the other, seem to thrive on making fools of themselves in the press.

35. Tara Reid
Heather Mills
Calum Best
Jesse Metcalfe
Bai Ling
Bobby Brown
Kim Kardashian
Pamela Anderson

Trainwrecks “Beyond Help”

Andy Dick

You couldn’t fix these trainwrecks even if you tried (as I’m sure many medical professionalshave)…

44. Michael Vick
Tom Sizemore
O.J. Simpson
Andy Dick
Anna Nicole Smith
Jonathan Rhys Meyers
Lil Kim

“Just Plain Odd” Trainwrecks

Jocelyn Wildenstein

Celebrities that, for one reason or the other, just make you step back and say – what the fuck? You’ll notice that this list is quite short – and with good reason: few celebrities ever manage to fuck their lives up this royally. Odd doesn’t even begin to describe their lives. Amy Winehouse, Britney Spears – too predictable and not a shadow on this bunch.

51. Michael Jackson
Lauryn Hill
Courtney Love
Jocelyn Wildenstein

by popcrund

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