The Premium The Premium The Premium

14 Celebs Who Are No Longer “Winning” at Life

Most Shocking
14 Celebs Who Are No Longer “Winning” at Life

There’s always a positive and a negative side to life and when we watch celebrities on the news, it’s easy to believe that they have it all good. Like, how bad can their lives ever be? “You have everything you ever wanted. Why are you complaining?” you’ve probably thought at some point in your life whenever a celebrity has something “trivial” to moan about. Yet, let’s face it, celebrities really do have it rough at times.

While most celebrities start off with promising careers, others ruin it for reasons we may never really understand. Granted, some situations may be out of their control. One minute they are loved by many, the next they are hated because of one bad movie role and their careers are over. Other times, it’s just due to poor choices. Drugs, alcohol, sex, and other vices can be so easily accessible in Hollywood, a star can overdo it to the point their destructive habits can cost them their personal relationships and careers. When you think about it, this is one of the aspects that makes us see these stars as human beings. Like you and me, famous people can feel like life is cursing them.

Many celebs, like Robert Downey Jr. for example, have made successful recoveries from being drug addicted, failing actors to becoming great Hollywood stars. Unfortunately, not everyone can be like RDJ. There are some Hollywood stars who have not bounced back from a sudden fall from grace and no matter what they do, they never seem to be able to climb back to the top.

So this list is about just that. Here are 14 celebrities who can’t seem to “win” at life anymore.

14. Tiger Woods – The Affairs



One of the greatest golfers on the planet, Tiger Woods had everything a highly successful athlete could ever want: money, recognition, fancy houses, and a good-looking wife and family. Unfortunately, everything came to a rapid decline overnight. He famously cheated on his now ex-wife Elin Nordegren, with numerous women, including NYC night club manager Rachel Uchitel. After a divorce and some rehab, Woods has had trouble regaining the status he once held as a top golfer. In 2015, he didn’t make the cut at the British Open Championship and the U.S Open. His love life seemed to improve when he started dating Lindsey Vonn but that relationship ended in May of last year.

13. Iggy Azalea – Controversy Follows Her



Australian rapper Iggy Azalea knows just as much as we do that her career is going downhill and fast. It feels like since the beginning of her music career, controversy followed her immediately. When she debuted with her track “Fancy,” Azalea sparked discussions on race, particularly in hip-hop music. Some even said she can’t freestyle or that her music isn’t legit rap. Azalea has even caused a rift in the LGBT community when she backed out of an event due to past homophobic comments. Her love life isn’t looking too good either when word got out that her NBA boyfriend Nick Young cheated her.

12. Chris Brown – Domestic Violence



Grammy Award-winning artist Chris Brown’s career had so much promise. His first record and Exclusive, his second album, went double platinum. Not only that, he was beginning to embark on a career in acting. In the midst of it all he found love with Rihanna but all that changed for the worse when it was reported that he had abused her. His career took a quick downfall since then and it has taken him many years to recover his tarnished image. Though Brown continues to make music, his violent behavior still makes headlines, including rumors of him and Rihanna getting back together after the altercation in 2013. They have since separated. In 2015, Brown became a father to a baby girl. So maybe his new dad responsibilities can help change his ways.

11. Lindsay Lohan – Can’t Hold A Job



Former child star Lindsay Lohan is definitely one of the stars on this list who seems to be experiencing the losing side. We are all well aware of her run-ins with the law. Lohan was arrested a couple of times for DUIs and her drama with both her parents, Dina and Michael Lohan, has been heavily publicized for several years. Ever since, Lohan has tried to revive her career and it’s been hit and miss. In 2013, she starred in the indie film The Canyons that was poorly received by audience and critics. Though she made her London stage debut in the West End 2014 production of Seed the Plow, it didn’t go off without a few hiccups. Her performance was received with mixed reviews due to nerves and forgetting her lines.

10. Courtney Love – Internal Turmoil



Former Grunge rocker Courtney Love has lived a rock n’ roll-filled life. She’s had a successful career as a singer for the band Hole. Most notably, she’s also known as the wife of Nirvana singer/songwriter Kurt Cobain and mother of Frances Bean Cobain. Since his suicide back in 1994, Love’s career and romantic life has been turbulent, including her relationship with her only daughter. The two had an estranged relationship so bad that it was reported that she did not attend her daughter’s wedding. Recently, Frances Bean Cobain has filed for divorce from her husband and Love and her daughter have gotten closer. Maybe this is a sign things are turning around for the both of them but only time will tell.

9. LeAnn Rimes – Homewrecking Ways



Country singer and actress LeAnn Rimes has sure come a long way in both her career and and personal life. The winner of 3 American Country Music Awards, two Grammys, and an American Music Award seemed to have it all until it all came crashing down in 2009 when she filed for divorce from her former husband Dean Sheremet. Shortly after it was revealed that the cause of it was her affair with Lifetime movie star Eddie Cibrian, who was married to Brandi Glanville at the time. These two went on to marry each other in 2011 but the affair tarnished Rimes’ image. Rimes has been on the slippery slope in her career and dealing with the consequences of her new marriage. In 2012, she went into rehab for stress and anxiety. Her recent album Today Is Christmas only sold 35,700 copies in the U.S.

8. Macaulay Culkin – Never Lived Up To Expectations


Home Alone star Macaulay Culkin has had his ups and downs since his days as a child star. Though he has impressive roles under his belt such as making appearances in Robot Chicken, Party Monster, and the 2004 flick Saved!, Culkin’s acting career has been more of a stop and go phase. Even so, he’s dabbled in music, forming an odd pizza-themed rock band called The Pizza Underground. As for love, he was in a long term relationship with actress Mila Kunis that later ended in 2011. Aside from experiencing twist and turns in his life, he still manages to impress audiences. More recently, he appeared in the web series DRYVRS, playing a now adult but mentally disturbed Kevin McCallister, recounting the events that transpired in Home Alone.

7. Azealia Banks – Rubs People The Wrong Way


Rapper Azealia Banks broke out into the scene in 2011 with her hit track “212” and now her career is going through a downward spiral. Banks, whose rebellious and sharply outspoken persona gained her love from fans, has now started rubbing people the wrong way. It all started with an incident when she called a pilot a “f*cking f*ggot*” in a feud while on a flight from New York to Los Angeles. She’s continued to use the term in other cases, claiming that it’s okay because she is bi-sexual. Her combativeness has been called “immature” and the more she acts out the more she alienates her fans and potential creative collaborators.

6. Raven Symone – She’s On The View…



This one can be debatable because the former Disney and Cosby Show child star has had a great career as a singer and actress. These days, she hasn’t had much of a hit, film or music wise. However, when she joined the cast of the talk show The View, Symone’s career started to take a bad turn. Known for having a seemingly wholesome and innocent charm, Raven has become more outspoken about who she identifies as and her opinions in general, which has pushed away even some of her biggest fans. She got into some hot water in 2015 when she said that she would not hire anyone if somebody had a “black” name on The View saying, “ I’m not about to hire you if your name is Watermelondrea.” Her comments infuriated members of the black community, some even cited her as being hypocritical. But nothing is worse than being called out by your own father. Her dad, Christopher Pearlman, called her out on her mistakes, calling them “inexcusable” but said he still has love for his daughter.

5. Amanda Bynes – Amanda Who?



Amanda Bynes, star of Easy-A, has had it rough the last few years. She first rose to fame on the Nickelodeon sitcom All That and has since went on to star in teen romantic comedies, being admired for her fun comedic chops. Unexpectedly, things took a bad turn when her behavior became erratic. In 2012, she announced her retirement from acting. Within that same year, she had a run-in with the law, getting arrested for reckless driving. In 2013, she was charged with marijuana possession. Her disturbing behavior eventually led to her receiving psychological evaluations for mental illness.These days she is taking back some control, focusing on a career in fashion.

4. Mel Gibson – Anti-Semitic Comments



Mel Gibson has had a long and successful career. Not only did he earn the status as an A-list actor starring in Lethal Weapon, Braveheart, and making women swoon in What Women Want, he also became a prominent Hollywood director, making The Passion of the Christ and Apocalypto. That film might have cursed him, because it was after the release of that blockbuster that things went south for Gibson. Of course, the infamous DUI arrest and anti-Semitic comments he delivered cost him a career but it got worse when Radar Online released the horrific tapes of his violent dispute with now ex-girlfriend Oksana Grigorieva. Little by little, however, Gibson has been making improvements, even scoring an appearance in this year’s Golden Globes- but who knows if he can truly fully recover from his downfall.

3. Shia LaBeouf – From Even Stevens To Music Videos



Transformers star Shia LaBeouf’s acting career was filled with much promise. Coming out of the Disney Channel scene as Louis Stevens in the hit show Even Stevens, he rose to bigger fame with the Transformers franchise and, yes, starring in Indiana Jones and the Kingdom of the Crystal Skull.. However, it’s Labeouf’s own professional decisions that led him astray from his rising star status, telling The Hollywood Reporter that he was done with making Hollywood films. Since then, he’s been more focused on independent and experimental films such as appearing nude in Lars Von Trier’s Nymphomaniac. He has also gone on to making performance art, which has led many to continue scratching their heads. The latest mainstream gig was appearing in Sia’s music video for “Elastic Heart.” Outside of his bizarre career choices, he has had some unfortunate legal troubles, including being accused of plagiarism. No matter how you look at it, he’s responsible for his poor career choices because people either hate him or love him now.

2. Charlie Sheen – Winner Winner Chicken Loser



“Winning” is no longer in Charlie Sheen’s vocabulary these days. Once having a very successful film and television career, his personal life has been riddled with trouble. First it was his marriage to Denise Richards. The two later divorced due to allegations of domestic violence, drug, and alcohol abuse. His tumultuous marriage to Brooke Mueller made headlines as well, due to similar reasons. Sheen maintained his partying ways, hanging out with his many “goddesses” and doing drugs. His self-destructive behavior got so bad to the point it was comedic, landing him a roast on Comedy Central. After all the ups and downs, he still seemed to remain in top form in his professional life. Despite leaving Two and Half Men, he returned to television in Anger Management. In 2015, Sheen announced that he had been diagnosed with HIV.

1. Bill Cosby – “Hello Friend”



No celebrity on this list has had a losing streak in life bigger than Bill Cosby. At first, it didn’t seem so for this huge star. Cosby, whose influence has spanned decades in the entertainment industry, all of sudden lost it all when more than fifty women claimed to have been sexually assaulted by him last year. These allegations started to surface in 2000 but it didn’t become a firestorm until comedian Hannibal Buress called him out full-blast during his stand-up performance. Still, no matter how many times Bill Cosby has denied any wrongdoing, organizations and institutions with once close ties to the comedian have backed away, and many of his awards have been withdrawn. Reruns of The Cosby Show were also cancelled. In December of last year, more charges (for aggravated assault) were filed in Pennsylvania for an incident that transpired in 2004.

  • Ad Free Browsing
  • Over 10,000 Videos!
  • All in 1 Access
  • Join For Free!
Go Premium!