20 Biggest Celebrity Trainwrecks

June 4, 2014 by  

20 Biggest Celebrity Trainwrecks, 20. Kanye West
Some people credit their art to their craziness. Kanye, God bless him, turns his craziness into art. Take the borderline-surreal bon mots of his Twitter feed: “I make awesome decisions in bike stores!!!” or “Fur pillows are hard to actually sleep on.” While more and more celebrities realize that Twitter enables them to make idiotic comments before thinking through the consequences, Kanye zagged in the opposite direction, deciding his fans needed even more Kanye. The result: You can now subscribe to Kanye’s life (only $4.99 a month!) and get webcam footage of Kanye, a list of what Kanye eats every day, and even a Kanye-centric documentary, simply titled Me. And if you don’t have the cash to subscribe, don’t worry; there’s a chance Kanye will randomly show up in your own life and regale you with a concert, as he did onboard a flight from Minneapolis to NYC when he took over the airplane intercom and performed two songs.

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19. Jose Canseco
Know when you’ve hit rock bottom? Here’s a hint: It could be when you’ve agreed to fight fellow washed-up all-star ballplayer Lenny Dykstra in a celebrity boxing match on FOX-all while sharing the fight card with pop culture luminaries like Octomom, Joey Buttafuoco, and Kato Kaelin (yeah, that Kato Kaelin). Though the fight never went down, it certainly seemed like bizarre company for a major league slugger who once earned upwards of $5 million a year. Canseco didn’t exactly hit a home run in retirement, either. His reputation went on the DL following the publication of Juiced, his 2007 tell-all memoir that outed former teammates like Mark McGwire for steroid abuse. Nor did it help when he threw down in yet another ‘celebrity’ boxing event against diminutive Eagles punt returner Vai Sikahema, who TKO’d Canseco in the opening minutes, despite Canseco’s 7-inch and 40-pound size advantage. That certainly doesn’t bode well for Canseco’s next rumored fight: Shaquille O’Neal. Keep those hands up, Jose.

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18. Herman Cain
Cain was among the more surprising candidates to surge ahead in the polls during the Republican debates. Known for his colorful personality and outspoken demeanor, the former National Restaurant Association CEO saw his Presidential aspirations begin to fade after pitching the widely criticized 9-9-9 tax plan-which, many critics argued, shifted more responsibility onto the poor. But it wasn’t policy that ultimately did him in-it was, like so many other men on this list, his problems with women. Cain denied the initial charges of sexual misconduct and adultery, but as more women came forward, Cain suspended his campaign in early December.

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17. Kim Kardashian
It may seem unfair to call Kim a wreck-her criminal record, far as we can tell, stayed spot-free in 2011. And we certainly never grew tired of looking at her-hell, we went so far as to name the reality star one of the hottest women of all-time earlier this year. It’s the ubiquity of the Kardashians’ romantic life, however, that gives love a bad name. You know the details: Kardashian split from NBA power forward Kris Humphries after just 72 days-guaranteeing all of us yet another Kim-and-Kourtney-centric news cycle, which, we suspect, may have been exactly the point. (Too cynical?) On the bright side, at least both parties benefited during the fallout. While ratings soared on Kourtney and Kim, the newly single Humphries manned up and signed a one-year, $8 million deal with the New Jersey Nets.

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16. Tracy Morgan
On 30 Rock, Morgan kills it as the brilliantly spastic, childishly coddled TV star Tracy Jordan. Part of the charm is that it’s often hard to distinguish where Morgan stops and Jordan begins, especially when he launches into a painfully un-funny rant about stabbing his son if his son ever acted gay, as Morgan told a crowd of fans in Tennessee last June. While Morgan issued a public-and seemingly heartfelt-apology, it was the sort of ugly, unhinged moment that made a lot of people question the comedian’s sanity-again-and whether or not we’ll be laughing the next time he loses it.

Tracy Morgan won’t win Father of the Year, but maybe he’ll contend next year if he learns the 8 things you should NEVER do in front of your kids.

15. Nicolas Cage
You’d think selling a comic book for a record-breaking $2.1 million would be a good thing, as Nicolas Cage did last November. In Cage’s case, we suspect the motivation behind the sale of Action Comics #1-Superman’s debut issue-wasn’t exactly worth celebrating. Thanks to an unreliable financial adviser and the not-inconsiderable cost of purchasing several homes around the world-including a possibly haunted mansion in New Orleans, a Caribbean island, and a rare dinosaur skull-the feds came after Cage in 2009 for owing millions in back taxes. Maybe that’s why, despite his pair of Oscar nods, he continues to headline questionable stuff like Bangkok Dangerous and Season of the Witch. This year, it looked like Cage had finally put the worst of his troubles behind him-and then we read GQ editor Jim Nelson’s first-person account of the actor drunkenly harassing patrons in a New Orleans restaurant. A month later, he had another run-in with the Louisiana cops, this time getting arrested for disturbing the peace. Two resolutions, Nick: Stay away from the French Quarter-and follow the sound financial advice of these six money geniuses, guys who’ve made fortunes and managed to hang onto them, too.

14. Randy Quaid
It can’t be easy being Randy Quaid. Your brother is handsome, respected character actor Dennis Quaid, while your last movie was something called Balls Out: Gary the Tennis Coach. No amount of sibling rivalry, however, can explain the depths of insanity to which Quaid and his wife Evi seem to have sunk, according to an epic Vanity Fair article. The Quaids claim they’re on the run from “star whackers”-a shadowy organization targeting major Hollywood stars (and, uh, Randy Quaid) responsible for killing Heath Ledger and even poisoning Jeremy Piven. Randy and Evi initially sought asylum from the Star Whackers in Canada after a failed jaunt to Siberia. Randy then went on the offensive in the most sensible way he could think of: writing and performing a song called (wait for it) “Star Whackers,” which blows the lid off of the conspiracy. Sleep soundly tonight, Hollywood-Randy Quaid’s got your back.

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13. Terrell Owens
Here’s some mind-blowing irony for you: NFL wide receiver Terrell Owens, who could charitably be described as “difficult to deal with” and “not a good team player,” wrote a children’s book in 2006 called Little T Learns to Share. Think about that for a second. T.O. once spit in opposing player Donte Hall’s face. He maintained a long-running feud with former Eagles quarterback Donovan McNabb that had all the dignity of a playground slapfight between two 12-year-old girls. And yet he thought he was qualified to teach kids about playing nice. That’s like Charlie Sheen running a DARE program. But that’s exactly the sort of clean break from reality that’s caused Owens to bounce from one team to the next-always leaving a new controversy in his wake-until recently becoming an unwanted, unrestricted free agent. Once upon a time he was one of the best wide receivers in the NFL, but as his own book could have told him, talent isn’t everything if you can’t play nice.

T.O. could’ve used a lesson in humility. This year, commit to being both a better husband and a better Dad with these easy 30-day New Year, New You plans.

12. Paz de la Huerta
We used to think Paz de la Huerta’s slurry speech and a droopy expression on Boardwalk Empire was just good acting-but lately, we’re not so sure it’s acting at all. Consider the evidence: Recently, de la Huerta allegedly crashed into a table, smashed a glass, and brawled with a member of Lindsay Lohan’s entourage. She didn’t fare any better at formal occasions, either: She was turned away from a Golden Globes after-party in 2011 for being heavily intoxicated. Time for Paz to spend a little less time in the speakeasy, and a little more time getting healthy. She could start by swapping the Old Fashioned for one of these perfect smoothie recipes in our guide to eating better.

11. DMX
Did you know that rapper DMX has a side career as an FBI agent? When asked to pay an outrageously high toll at JFK Airport in 2004, he responded by crashing through the tollgate, then claiming he was with the Feds and needed to commandeer another driver’s vehicle. The airport toll: $9. His bail after arrest: $15,000. A variety of legal problems-many of them stranger than fiction-have dogged DMX ever since. Most recently, he got arrested in Arizona for doing 102 in a 65 mile per hour zone on a suspended license. Thankfully, it seems like the troubled hip-hop star is finally prepared to chill out. In December, DMX visited with wounded U.S. troops. He also committed to the VH1 reality show Couples Therapy, as well as Dr. Drew’s Lifechangers. It’s progress. Another step? Getting a toll tag.

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10. Jesse James
Only a few weeks after thanking her husband Jesse James during her acceptance speech for Best Actress at the 2010 Oscars, Sandra Bullock learned that he was a serial adulterer whose conquests included a tattoo model, a fetish model and a stripper. Their marriage quickly imploded-and while we felt for Bullock, you have to wonder how she didn’t see any warning signs. James, after all, counts a porn star among his two ex-wives and once posed for a photo while wearing the hat of a Nazi soldier and giving a “Heil Hitler” salute. Even more clueless: LA Ink reality star Kat Von D, who dated James after his split from Sandra and later claimed in a Facebook post that he cheated on her with 19 women during their relationship.

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9. R. Kelly
Comedian Aziz Ansari perfectly summed up the appeal of R. Kelly when he described the artist as a “brilliant R&B singer/crazy person.” Just how crazy? Jay-Z filed a $90 million breach of contract lawsuit against Kelly for causing the collapse of their 2004 Best of Both Worlds tour with his frequent emotional meltdowns. In the oddest incident, Kelly abruptly left a St. Louis concert to work the drive-thru at a nearby McDonald’s. And when a sex tape involving a man who sure looked a lot like Kelly surfaced in 2002, Kelly suggested that he’d been framed-with the culprits digitally imposing his face over another man’s body. Before you criticize Kelly, however, bear in mind that his fantastic new song “Shut Up” claims his music is responsible for the conception of every child since the ’90s. So for the teens reading this, R. Kelly says you’re welcome.

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8. Gary Busey
Busey could be toying with us. His erratic, spaced-out weirdo schtick is a role he’s milked masterfully in everything from Entourage to Vitamin Water commercials. Busey’s willingness to poke fun at his (perceived) insanity endears us to him, despite the headlines claiming he once drunkenly tackled a woman at the airport, or snorted cocaine off his dog. Crazy or not, Busey at least has his redeeming qualities-he once donated his Celebrity Apprentice winnings to a charity that funds brain research, and last year he waited on the scene to help save victims of a car crash. We’re not sure which proved more terrifying for the victims, though-the accident itself, or the knowledge that Gary Busey was sprinting to the rescue.

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7. Arnold Schwarzenegger
For decades, Schwarzenegger enjoyed a nearly unparalleled run of success-from Mr. Universe to the world’s highest-paid action star to one of America’s most powerful politicians. And then, as it so often happens, his past caught up with him. In a year rife with political bombshells-remember Anthony Wiener?-the former California governor caused the biggest ripples when he confirmed that he’d fathered a child 14 years prior with his then-housekeeper, Mildred Baena. Worse, the humiliating public disclosure ultimately ended Schwarzenegger’s 25-year marriage to Maria Shriver. Since then, Schwarzenegger’s kept a low profile-for him, anyway-but the 64-year-old now appears ready to reemerge, with plans to resurrect his long-dormant acting career in the upcoming action flicks The Expendables 2, Last Stand, and Black Sands. Don’t let your relationship get terminated in 2012. Follow these 30 easy strategies to be a better husband.

6. Lenny Dykstra
It was bad enough when the stories came out in The New Yorker and ESPN circa-2009 detailing Dykstra’s many financial mishaps, but the already bizarre story took an even crazier turn in 2011. In June, the former World Series champion was charged with 25 criminal counts of federal bankruptcy fraud. A month later, he was jailed on grand theft auto charges when a dealer claimed the former Phillies star used bogus information to lease a luxury car. And even that wasn’t the end of it: Dykstra was charged yet again in August-this time for allegedly exposing himself to a series of women who answered a housekeeping ad. If convicted on the fraud charges alone, “Nails” could spend up to five years in prison, where the tough nickname won’t do him nearly as much good.

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5. The Jersey Shore Cast
We couldn’t pick just one-the tanned and freshly laundered castmembers of Jersey Shore all deserve a place here, far as we’re concerned. Where to begin? Snooki’s sloppy hookups? The Situation’s out-of-control boozing? Pauly D’s near-daily trips to the tanning salon? The fist-pumping jocks and their high-heeled MTV cohorts make a full-time profession out of getting wrecked on camera. And we’ll be the first to admit the results often make for irresistible, can’t-look-away programming. The show’s popularity irked New Jersey Governor Chris Christie so much that in February he lashed out at program, claiming it brought negative publicity to the state. Christie might want to turn some of that criticism inward-his massive girth was a frequent subject of debate as he explored the idea of a Presidential run.

We’ve got at least 30 ways the future Presidential hopeful could slim down this year and get back in shape. Hell, even Snooki might drink to that.

4. Andy Dick
Once upon time, Andy Dick was the lovably eccentric star of NewsRadio. Today he’s an embarrassing fixture of online gossip sites like TMZ and Perez Hilton. The charges levied against him include public urination, disorderly conduct, and much, much more. In May, he got arrested for disturbing patrons in a Marie Callendar’s restaurant in California. A few years before that, he got hauled away from a Buffalo Wild Wings. In January, Dick was tossed from the AVN awards-the Golden Globes for porn stars-for harassing adult film star Tera Patrick. It’s been a sad and relentlessly cringe-worthy turn for what was once a very promising career.

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3. Courtney Love
It’s hard to counter your reputation as a troubled celebrity when there are stories like “Courtney Love insists she didn’t burn apartment” running in the paper. Despite appearances, the former Hole lead singer does seem to have taken legit steps to clean up. That’s what makes it all the more heartbreaking when, say, the New York Times dispatches a reporter for an interview and he writes about finding Love knocking over martinis and walking around nkd in her hotel room. Or when she goes on stage in Brazil and allegedly flashes the crowd, asks a fan for “a chapstick for my herpes sore,” and rants about Dave Grohl. We could do without the commentary, but Love’s still worth hearing when she’s clean. This year, we hope the sobriety sticks.

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2. Charlie Sheen
A complete account of Sheen’s year could fill a novel, and the chapter headings might read something like this: Terrified hookers in closets! Calling Thomas Jefferson a pssy! The nationwide tour that flamed out! Attempts to create a “porn family”! (C’mon Charlie, your real father is President Barlet. Isn’t that good enough?) By far the craziest thing Sheen did was lucking into one of the best gigs on Earth-sleepwalking through Two and a Half Men while earning a staggering $2 million per episode-and then scotching it by starting a meaningless feud with show creator Chuck Lorre, a feud that included challenging Lorre to a cage fight. We’ll put that first on our list of ways not to get promoted.

For strategies that will help you move ahead, check out this month-long guide to finally nabbing that promotion. Tip 30: Find a mentor. Sorry, Charlie-you’re out of the running.

1. Lindsay Lohan
Last month’s Playboy spread (yeah, we Googled it, too) gave every red-blooded American male an unforgettable, bottled-blonde reminder of exactly how far Lohan’s career has tumbled since the innocent days of Mean Girls and The Parent Trap. She’s remained a tabloid fixture for nearly half a decade since, starting with a pair of DUIs in 2007, followed by a short-lived fling with girlfriend Samantha Ronson, and a few visits to rehab for good measure. Despite her checkered criminal past, however, we’ve never given up hope that Lohan might pull herself back together. We’d even settle for another Mean Girls sequel (yeah, there was already a second one) at this point. Even in the valleys of her career, she’s always shown modest signs of promise-whether it was her solid supporting effort in the indie political drama Bobby, or her viral, hilariously self-deprecating fake eHarmony ad for the website Funny or Die in 2009. It may take a long time before she earns back the trust of a legit director-even Donald Trump confessed he’d be reluctant to take Lohan on The Apprentice (ouch!). If she doesn’t clean up soon, 2011 will prove to be the year we saw all of Lohan. And 2012 will prove it was the last.

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