The 54 Worst Celebrity Trainwrecks, Ever

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

Michael Jackson

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
2. Amy Winehouse
3. Britney Spears
4. Lindsay Lohan
5. Paris Hilton
6. Kirsten Dunst
7. Mischa Barton
8. Michelle Rodriguez
9. Kiefer Sutherland
10. Kate Moss
11. Naomi Campbell
12. 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
14. Daniel Baldwin
15. Mel Gibson
16. Heidi Fleiss
17. Tom Cruise
18. Paula Abdul
19. David Hasselhoff
20. Keith Richards
21. Sharon Stone
22. 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
34. Avril Lavigne

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
36. Heather Mills
37. Calum Best
38. Jesse Metcalfe
39. Jordan
40. Bai Ling
41. Bobby Brown
42. Kim Kardashian
43. Pamela Anderson

Trainwrecks “Beyond Help”

Andy Dick

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

44. Michael Vick
45. Tom Sizemore
46. O.J. Simpson
47. Andy Dick
48. Anna Nicole Smith
49. Jonathan Rhys Meyers
50. 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
52. Lauryn Hill
53. Courtney Love
54. Jocelyn Wildenstein

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