20 Photos Of Hollywood's Hottest Trainwrecks

Everyone loves a good scandal. And when you pair celebrity status with train wreck behaviour, you have the “secret sauce” of front cover news.

The phenomenon of rubbernecking refers to the way that we crane our necks to get a better view of something we can’t help but stare at. It’s also connected with human nature and our morbid curiosity when it comes to disaster. When we’re on the road and there’s a car accident, much of the traffic on the road following the incident has nothing to do with clearing away the debris and the emergency personnel getting there (although that is some of it) – traffic slows because others, take their eyes off of the road and can’t help but gawk at the wreckage as they pass by.

Our interest in celebrity scandal, true crime, sensationalized news, or war is no different than rubbernecking at a car accident – it’s human nature.

Someone becomes a celebrity from a varied combination of talent, good looks, and luck. They have that special something that draws us to them – they have that quality that makes us want to watch them. Pair their celebrity status with train wreck behaviour and you have the “secret sauce” of front cover news. Some, thankfully, make it out to the other side with lessons learned, whereas others become cautionary tales about addiction and self-destruction. Here are 20 of Hollywood’s most beautifully tragic celebrities in all of their rubberneck-inducing glory.

20 Anna Nicole Smith

Famous for her good looks and killer curves that were often compared to Marilyn Monroe, Anna Nicole Smith also saw a tragic end that came way too early. The Guess and Playboy model made tabloids when she married a much, much older octogenarian, which many presumed was solely for his money. When her elderly second husband passed away, she launched into a legal battle over his estate. In the last six months of her life Smith was in the tabloids due to the death of her son Daniel and a paternity/custody battle over her newborn daughter. Much like Monroe, Smith’s life took a final tragic turn when she was found dead in a hotel room from an overdose of prescription pills she’d become addicted to in the final months of her life.

19 Kate Moss

The woman who defined “heroine chick” in the 1990s became one of the most well-known super models of all time. Kate Moss was the face of campaigns for Calvin Klein, Burberry, and Rimmel with a lengthy career spanning decades. There are rumours that she began her descent into a drug addled existence when she was dating Johnny Depp in 1994, and she was nicknamed by friends “The Tank” for her ability to consume two or three grams of cocaine in one session, and wash it down with an entire bottle of vodka. It was her romantic connection with Babyshambles Pete Doherty that got her the nickname of Cocaine Kate when photographers blew the lid on her penchant for powder. Moss lost several of her contracts as a result of her bad habits. At a fashion event in Cannes recently Kate got into a fight at an after party with another guest. Thankfully Mary J. Blige was there to calm the situation.

18 Tara Reid

If there were photos in the Urban Dictionary, Tara Reid’s would be plastered right beside the entry for “Hot Mess”. Tara Reid was a Hollywood “It Girl” in the 1990s making a name for herself in The American Pie franchise, Van Wilder, and The Big Lebowski. Unfortunately it didn’t take long for the celeb to be better known for her hard partying ways and need for plastic surgery, liposuction and a better stylist. The star has had several wardrobe malfunctions where she loses her top, most notably at Sean Combs (Puff Diddy’s) birthday celebration. Although she has been able to get some success in embracing campy roles for the Sharknado franchise, she showed up at many promotional opportunities completely incoherent, showcasing her train wreck tendencies and D-list portfolio (and no, we’re not talking about the boob jobs).

17 Mary Kate Olsen

When your career peaks before you get out of grade school there really is nowhere to go but down. Being in the limelight for your entire life can’t be an easy gig, particularly those awkward teen years when creepy shock jocks and radio DJs began countdowns to the Olsen twins 18th birthday (AKA when they became “legal”). Mary Kate Olsen has suffered from a long suspected eating disorder, has been hospitalized for kidney infections and is most commonly photographed with her signature “diet” of coffee and cigarettes. The twin was connected with the untimely death of Heath Ledger. The two were believed to be dating when Mary Kate’s masseuse found Ledger dead, calling Olsen three times before connecting to emergency services. Mary Kate has kept a reasonably low profile since, with the exception of her May-December romance and marriage to Olivier Sarkozy.

16 Avril Lavigne

There is a lot of room for jokes here about Avril Lavigne and her failed marriages to both Deryck Whibley and Nickleback’s front man Chad Kroeger, but they’re really the least of the drama for the former Sk8er Girl. Lavigne has been accused of stealing music and not giving credit to others on three separate occasions. The former role model has also been blasted for her “shades of Gwen Stefani” cultural appropriation of her 2014 “Hello Kitty” video that is ripe with perpetuating Asian stereotypes. The video and song is offensive on so many levels that we don’t even have time to chip away at that ice berg of terrible after we wipe away our pastel pink, sprinkle soaked vomit. The star has been accused of underpaying her dancers, despite having sold over 30 million records, and being a straight up D-Bag to fans and haters alike.

15 Lindsay Lohan

Lindsay Lohan was a made-for-TV movie before she was legally able to drink. The star is “celebrating” the tenth anniversary of the first time she was charged with driving under the influence and possession of cocaine when she lost control of her Mercedes in an epic car crash that we still can’t turn away from. In the years since this “Mean Girl” has flunked drug test after drug test, and been in and out of rehab. In addition to the toll that her hard partying ways have taken on her career, the once fresh faced hottie has aged quickly from her former self. Showing a teen the impact drugs and booze has had on sucking away both Lohan’s soul and youth would make for an excellent public service announcement. When she was just 25, paparazzi honesty mistook 66 year-old Blondie singer Debbie Harry for Lohan, despite their 31-year age difference, ouch!

14 Pamela Anderson

A couple of poor choices can derail the best of us, and former Playboy Bunny Pamela Anderson is no different. The Baywatch beauty made a career out of showing off her fantastic figure, and even managed to use her celebrity to advocate for causes she really believes in, like Pam’s work with PETA. Pretty Pammy’s taste in men and indecision with her flotation devices seem to be her Achilles heel. She has a love of bad boys, marrying Tommy Lee, 96 hours after she met him. Souvenirs from Anderson’s marriage to Lee, with the exception of two sons who she adores, includes contracting Hepatitis C from sharing tattoo needles with the drummer, and domestic violence charges against Lee. Her marriage to Kid Rock lasted less than six months, which still beats her two month marriage to Rick Soloman. Hopefully she finds her prince in hard rock armor one day!

13 Paris Hilton

Remember when Paris Hilton was one of the only celebrities who was famous for her ability to get on a VIP list? The good old days! First there was the sex-tape scandal, the rotating cast of boyfriends, and then she took a bit of a step away from the spotlight, or so we thought. Then last September, while partying with her entourage in Las Vegas, she was charged with felony drug possession. With potential drug charges that could carry a maximum of four years in prison, the car she was in was pulled over on the main drag after an officer smelled marijuana coming from the vehicle. The arresting officer wrote, “As she began to open [the purse], I saw a small bindle of what I believed to be cocaine in a clear baggy begin to fall from the purse and into my hand.” Thankfully for Hilton the whole thing was deemed a “misunderstanding” and all charges were dropped.

12 Robert Downey Jr.

Robert Downey Jr. is so talented and so darn charming no one wanted to believe the tragic addiction that engulfed him. The star says that since his father was also an addict, he was constantly surrounded by drugs. His father, who now regrets it, first allowed his son to use marijuana at age six, and Downey Jr. has said, “When my dad and I would do drugs together, it was like him trying to express his love for me in the only way he knew how." As he aged, and his career soared, Downey spent all of his free time abusing drugs or in pursuit of more drugs. In April 1996 things hit bottom when he was arrested for possession of cocaine, heroin, and marijuana. After finally cleaning up for what we hope is for good in the early 2000s Downey had to pay for his own insurance on set since he was such a risk to cast in anything. Since then, this Iron Man has seen his career turn to pure gold!

11 Amanda Bynes

It’s a pretty good sign that when Courtney Love tweets out a “pull it together” about your antics that you need to get some help. Amanda Bynes was once a sweet-girl-next-door, and then worked her way to undo her squeaky-clean image by posing for Maxim and announcing a hiatus from acting. With that not being enough to revamp her parental guidance recommended make-over she decided to add a few DUI allegations to her portfolio. Her breakdowns include everything from locking herself in store dressing rooms for hours to getting tossed from a spin class for erratic behaviour. In July 2013, she was put on an involuntary psychiatric hold after lighting fire to a complete stranger’s driveway. Hopefully she’s getting the help she needs to lead a long, healthy, and quiet life outside of the spot light.

10 Britney Spears

Britney, Britney, Britney, remember when she wore a school girl outfit and used to show off her fit belly? When she married professional leech Kevin Federline it was the beginning of a very long line of bad decisions. After three years of marriage and two children with the “Fed” both filed for sole custody of their children. Britney Spears began partying commando with Paris Hilton, and attacked a paparazzi with an umbrella. Following the incident where she shaved her head and checked herself into rehab the star addressed concerns about her recent actions saying, “Trust me, I get it, I know I've been far from perfect and the media has had a lot of fun exaggerating my every move ... I look forward to coming back this year bigger and better than ever." Not every train wreck story has a sad ending, Hardworking Brit has managed to pull herself up and now has a regular Las Vegas Show. Go Brit!

9 Eva Mendes

Eva Mendes is a hot lady. She once ranked number seven in Maxim Magazine’s Hot 100 Issue and was the cover model in November 2007. She’s had notable roles in movies including Training Day and Hitch. Unfortunately, celebrity and stardom caught up with her, causing the actor to check herself into rehab at the famed Cirque Lodge in Utah. Coming out the other end of addiction the star is proud of her and other recovering addict’s accomplishments. Mendes has said, “I’m proud of people who have the determination and the fearlessness to actually go and face their demons and get better. This is a life or death situation.” In recent years Eva has focused on her family, notably her partner, Ryan Gosling and their two daughters. Mendes is proof that even if your life is a mess, you can turn things around.

8 Justin Bieber

You better "belieb" this little punk is going to make this list for bad behaviour. First off, as a Canadian, I feel a need to apologize for us producing Justin Bieber. Not only are his records blowing up, so are the locations of his arrests: He’s nearly hit the big house in Toronto, Miami, and Brazil. In addition to acting out like a spoiled brat, egging his neighbour’s place, fighting people and vandalism, he’s also following in the footsteps of rapper Lil Wayne and his love of getting all tussed up on cough syrup. It’s been reported that the singer’s beverage of choice is called “sizzurp” (we wish we were joking) which is a cocktail made of prescription cough medicine, sprite, and a single Jolly Rancher. And remember that time he urinated in a janitor’s bucket? Stay Classy Justin!

7 Kirsten Dunst

Kirsten Dunst started her road to stardom at a young age, first making a name for herself in the iconic role of Claudia in the film adaptation of the Anne Rice novel, Interview With A Vampire. Her moment in the spotlight seemed as if it would never end, as she became a household name and even secured the role in the Spiderman series as Mary Jane Watson alongside Tobey Maguire, whom she also dated. When Dunst began dating Razorlight lead singer Johnny Borrell, the rock star lifestyle that followed caused trouble. After several instances of being photographed stumbling around, and reports of erratic behaviour, the starlet was given cruel nicknames like “Kirsten Drunk”. In 2008, she voluntarily checked herself into rehab for depression while rumours of alcohol abuse and drug use surrounded her. Of her Hollywood treatment Dunst says, “It's unfair that an artist is expected to speak really well in public and have skin tough enough to withstand sometimes really hurtful criticism, but also, in order to do the job, be really sensitive and in touch with their feelings.”

6 Kanye West

At this point in his career, Kanye West is better known for his rambling rants than music, although his ability to continue to grab our attention while spouting out pure verbal diarrhea is pretty impressive. In 2009, he decided to right wrongs by letting Taylor Swift know mid-acceptance speech how undeserving she was of praise, in one of his most “Memed about” moments. The arrogant diva feels the greatest pain in his life is that he will never be able to watch himself perform, and had the audacity to pose on the cover of The Rolling Stone dressed as Jesus Christ in 2006. In his defence, maybe Kanye didn’t know who he was dressed as, after all he boasts being a “proud non-reader of books”, because they are too “wordy and self-absorbed”. When he’s not randomly accusing MTV of racism, he can be found fighting all the haters, since his relationship with Kim Kardashian is like a modern day Romeo and Juliet. Just smile and nod, and back away slowly people!

5 Demi Moore

Demi Moore was one of the original brat pack, so you have to imagine that she has her share of stories of what went on behind the scenes “back in the day”. She seemed to have settled down and married Bruce Willis, where they had some beautiful children. When her marriage ended, she decided to trade up to a younger fitter model, and ended up marrying Ashton Kutcher who is 16 years younger than her. Despite being in great shape and looking amazing for her age, she handled their 2011 breakup very badly. Due to depression from the heartbreak she lost a lot of weight and ended up hospitalized for taking nitrous oxide “whip-its” capsules (which provide a very short high when inhaled). Demi has been acting again, recently taking a cameo on Empire. Here’s hoping this 1980s lady has happier days ahead.

4 Naomi Campbell

Maybe it’s all of the food deprivation that keeps supermodel Naomi Campbell on the edge of a hangry meltdown at any given time. This is the woman who has admitted to assaulting a personal assistant with a cell phone, she’s thrown a be-dazzled BlackBerry at a housekeeper, and even had a row with two police officers when she was at Heathrow airport. The super model also managed to score a five year ban from British Airways for her bad behaviour. When she was sentenced to community service for her nonsense she arrived in style, keeping a diary of her sentence for W Magazine, with photo spread, and showing up to serve some of her community service time in a sequinned silver Dolce and Gabbana Gown. The model who is known for her “you’re not here to make friends” attitude towards modelling and business will continue to inspire awe and fear in anyone within a cellular phone throw’s distance for years to come.

3 Lily Allen

Lily Allen was a hot mess, and hopefully she’s gotten it together, either ways she's managed to produce some great music and become a mum. When she was young she attended 13 schools where she was expelled for smoking, drinking and performing oral “dictation”. Her pastime while she was finishing up school also included dealing ecstasy, until she finally dropped out at age 15. She spent four weeks in Priory (a UK recovery spa) following feeling suicidal. She is very talented, but still has her moments of controversy, whether it’s fighting with people on Twitter, or getting so intoxicated while drinking Jack Daniel's straight out of a bottle at a street festival that her boyfriend needs to carry her out. Lily herself has commented that she wishes she was better at handling, “Press. Shutting up. Self-censorship.” In 2007, Allen was arrested for reportedly assaulting a paparazzi.

2 David Hasselhoff

While he was always “the old guy” on Baywatch there was no denying that David Hasselhoff was a huge sex symbol. While he’s always been more popular in Europe than he was in North America, there was something casual cool about the guy from Knight Rider that not even his nonsensical music videos could destroy. Instead the star self-destructed care of his alcoholism. In 2007, a home video released gave people a glimpse of the real “Hoff” proving that sometimes what happens in Vegas gets released for the entire world to see. The video was of David drunk beyond belief in his Vegas hotel room disgustingly trying to eat a cheeseburger while his daughter begged him to just stop drinking. The star keeps on trying to get sober, but keeps falling off the wagon. David, we’re wishing you a dry and sober comeback, even if you’re on the beach.

1 Steven Tyler

While he’s not traditionally Hollywood Handsome, he’s still a rock star in his own right and has made women scream louder than he can for nearly fifty years. As one half of the toxic twins, Steven Tyler is no stranger to controversy. This classic rock god once fuelled his flames with every drug imaginable to man - nowadays he plays host to contestants on reality TV. One of his most heinous moments occurred in the 1970s when he talked a mother into signing over custody of her daughter so that they could travel interstate together without him worrying about getting arrested. In his 1997 autobiography, when talking about the relationship, which lasted for three years of groupie love on the road, Tyler has said of the time, “(she) lost her childhood. I lost my mind”.

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20 Photos Of Hollywood's Hottest Trainwrecks