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Posted at 12:48 PM ET, 12/17/2009

Biggest celebrity train wrecks of the '00s?

By Liz Kelly

Potential train wreck winner: Lindsay Lohan's July 24, 2007 mug shot. (Reuters)

I think we can all agree that Tiger made a late play for the title of "biggest celebrity train wreck of the decade," but below is my list of the core contenders. Have a read, cast your votes in the ranking poll, then join me at 2 p.m. ET when we'll debate the inclusions, exclusions and your take.

1. Tiger Woods: What began as a sketchily-explained late-night car crash has blossomed into a full-blown sex scandal, with alleged mistresses still coming out of the woodwork, an imploding marriage and skittish sponsors dropping their erstwhile golden boy.

2. Britney Spears: Sure, she's back on track now, but two years ago Brit was bopping around L.A. using a cringe-inducing British accent, shaving her head, losing custody of her kids, bashing an SUV with an umbrella and turning in one of the worst performances ever captured on MTV.

3. Mel Gibson: Remember when we all kind of considered Mel Gibson to be a Hollywood untouchable? He was an actor/filmmaker on a par with contemporaries like Clint Eastwood. That is until 2006, when he was pulled over and slapped with a DUI, during which episode he also unleashed an anti-Semitic tirade on the cops. Oh, not to mention that reference to one female officer as "sugar****." Classy.

4. Amy Winehouse: Now Amy's antics are old hat, but for a while there the "Rehab" singer's out-of-control binges, fights with then-husband Blake Fielder-Civl and creepy YouTube videos had us enthralled.

5. The Jennifer Aniston/Brad Pitt/Angelina Jolie saga: This vortex of a love-triangle may be as deadly as Bermuda's own triangle considering the years we've lost to a mysterious fascination with the three actors. Although Pitt and Jolie have been together since 2005, we're still polarized by "poor Jennifer" and "temptress Angie."

6. Kanye West: Another year, another VMA moment. This October, West became an overnight Internet sensation (and suffered a huge loss of cred) when he interrupted Taylor Swift's VMA acceptance speech to protest that Beyonce really should have won.

7. Chris Brown: In one night, Brown went from rising star to thug after news broke that he had assaulted girlfriend Rihanna after a pre-Grammy party.

8. Martha Stewart: After a conviction for insider trading, the domestic diva spent five months in a West Virginia federal prison camp. Of course, leave it to Martha to make bigger headlines for the prison-crocheted poncho she wore upon release. She's now comfortably back where she left off, helping us stock our holiday bars and schooling us on the finer points of corn cakes with Christmas caviar.

9. Anna Nicole Smith: The tragedy of Smith's life was undeniable. After her death at a Florida casino in 2007 due to an overdose (just months after the death of her teenaged son), a fierce battle for control of her estate and daughter Dannielynn began. Photographer Larry Birkhead was eventually proved to be the child's father.

10. Lindsay Lohan: Her strong performances in "Freaky Friday" and "Mean Girls" early in the decade indicated there was nothing but success in Lohan's future. Then came the arrests, stints in rehab, evaporating career, messy relationship with DJ Samantha Ronson, exploitative parents and an itchy Twitter finger, all of which contributed to Lilo's transformation from Disney darling to hot mess.

Agree with my rankings? If not, rearrange below:

Note: We're having a spot of trouble with our polling software. Keep voting -- your choices are being recorded -- and we'll display the results as soon as we get this fixed.
More Best of the Decade coverage.

By Liz Kelly  | December 17, 2009; 12:48 PM ET
Categories:  Celebrities, Friday Lists, Insta-Polls  
Save & Share:  Send E-mail   Facebook   Twitter   Digg   Yahoo Buzz   StumbleUpon   Technorati   Google Buzz   Previous: Emma Watson named highest-grossing actress of decade; Gosselin divorce 'imminent'?
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After rank ordering, I realized I placed the women generally higher than the men regardless of the severity of the trainwreck. (Smith goes to the top; everyone else might be crazy but at least they're alive.) I think it is because men recover from media trainwrecks faster. Either we the public are more likely to forgive or because we expect boorish behavior from them. Either way, my apparant sexism disturbs me.

Posted by: DCCubefarm | December 17, 2009 1:40 PM | Report abuse

Hey DC, don't be so hard on yourself. I don't think you're sexist. It is true in the cases listed above, that the top trainwrecks do happen to be women. I had a similar thought process too. I ranked Smith on top b/c she died (worst outcome possible-only thing worse would be if your wreck killed someone else so I guess she might be considered to have pts for that too-remember son died too). Next is Amy Winehouse b/c despite the relative lack of Amy news, I, and probably none of you, would be very suprised if we heard her wreck turned fatal. Lilo of course is up there as well for same reasons but for some reason I can't put my finger on, does not seem as bad as Amy. Maybe b/c she hasn't had to have her stomach pumped on a regular basis.
Chris Brown would be the highest ranked guy on the list in my view.
I wouldn't consider the Brangelina vs Jen story a trainwreck b/c it didn't really hurt them or their careers now did it?

Posted by: hodie | December 17, 2009 2:13 PM | Report abuse

hodie, following your logic, MJ's ultimately fatal use of general anesthesia as a sleep aid makes him a major trainwreck of 2009 too. Sad to say.

Also, Carridine's auto-erotic self-aphyxiation.

Posted by: Nosy_Parker | December 17, 2009 3:17 PM | Report abuse

I agree with Nosy on MJ. Train wreck of all train wrecks.

I also don't agree about Martha Stewart. That lady is tough as nails.

Difficult to judge Tiger Woods since that one is still going off the rails.

Posted by: kvs09 | December 17, 2009 3:30 PM | Report abuse

kvs, agree with you re Martha Stewart (even though I'm no fan of hers). She paid her debt society, then got on with her life without much public whining.

Posted by: Nosy_Parker | December 17, 2009 3:35 PM | Report abuse

Liz only leaves Courtney Love off the list to antagonize me.

Posted by: quintiliusvarus | December 17, 2009 3:48 PM | Report abuse

Tiger Woods train wreck is too new to qualify. It just happened. He was fine for most of the decade.

To me, the most deserving is consistently in the news throughout the decade. Good or bad. Lindsey, Courtney Love, Anna Nicole Smith with her never ending court battles, then her tragic death. MJ with all his weirdness consistently throughout the years ending with the weirdness of his sudden death and the family still living off his memory.

Martha Stewart was a blip on the radar.

Posted by: epjd | December 17, 2009 3:54 PM | Report abuse

Don't forget Mel "High and Mighty" Gibson cheating on his wife and fatheris another kid with some Russian bimbo.

Posted by: EricS2 | December 17, 2009 4:00 PM | Report abuse

agree with you Nosy, but MJ was not offered as a choice above. I prob wouldn't choose Carradine b/c he wasn't a story until he died.

Agree with the others, also, that Martha Stewart was not a trainwreck. Even when she went to prison, you knew she was going to be ok.

Posted by: hodie | December 17, 2009 4:12 PM | Report abuse

Oh, but Nosy, I would submit Carradine's name for a Darwin Award!

Posted by: hodie | December 17, 2009 4:13 PM | Report abuse

Oh, but Nosy, I would submit Carradine's name for a Darwin Award!

Posted by: hodie | December 17, 2009 4:13 PM

And his Darwin Award would be a leg-shaped lamp wearing fishnet stockings.

Posted by: northgs | December 17, 2009 4:54 PM | Report abuse

MJ was not offered as a choice above

Doc, ya gotta dare to color outside the box from time to time!

Posted by: Nosy_Parker | December 17, 2009 5:43 PM | Report abuse

Martha Stewart was NOT convicted of insider trading. While she was initially charged with securities fraud, the charges were downgraded twice, and she was ultimately convicted of much less serious charges, including making false statements to investigators.

Even a gossip columnist should know the difference between an indictment and a conviction and bother to get the facts right, especially when it comes to a criminal conviction.

Posted by: WashingtonDame | December 17, 2009 6:58 PM | Report abuse

I agree with the above list of celebrities. Tiger woods deserves to be at the top.

Posted by: aaron78600 | December 18, 2009 6:27 AM | Report abuse

funny thing is, there's not that many 'train wrecks' on that list. Most of those people are still very well-liked and highly successful

Posted by: killerrob | December 24, 2009 5:06 PM | Report abuse

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