15 Messed-Up Celebs Who Will Never Bounce Back

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When they say Hollywood is all about glitz and glamour, that’s just one side of the story.

Upon hearing the term “Hollywood celebrity,” our minds usually paint a picture of people looking like gods and goddesses that personify physical perfection. They look totally dolled up and gorgeous with absolutely glowing skin, the perfect makeup and hairstyles and the priciest wardrobe. But when they say Hollywood is all about glitz and glamour, that’s just one side of the story. Reality tells us that while being in the multi-billion international business is truly life-changing, the turnout isn’t always a positive one. In fact, it has become quite common for some ultra-famous celebrity to make poor life decisions and consequently, become a bad case of Hollywood mess-up. Here are 15 celebrities whose mess-ups were so colossal, they never had the chance to ever bounce back.


Chris Brown was at the height of fame in 2005. However, his career was overshadowed by his poor behavior that reached its peak in a violent fight with then-girlfriend and famous singer Rihanna in 2009. This cost him his reputation, his endorsements and his career as an artist. Not only that, Chris was also tested for cannabis and had a violent fight with another girlfriend who was granted a temporary restraining order against him. In March 2015, Chris’ felony case from the assault on Rihanna was formally ended and he has released a documentary detailing the unfortunate case. While Rihanna may have found it easier to forgive, the public certainly never forgets—and it shows in Chris’ unsuccessful attempt for a comeback as an artist.


Amanda Bynes used to be a promising star who lit up television screens with her 1999 program The Amanda Show on Nickelodeon, plus a few films and a TV series thereafter. However, upon reaching her mid-20s and after cresting the peak of her fame, Amanda started behaving oddly. She fought with fellow celebrities on Twitter and then stated she would “take a break” from acting. The straw that broke the camel’s back was her series of run-ins with the law for possession of marijuana, misdemeanor and DUI. Notorious for exhibiting dangerous behavior behind the wheel, she was so troubled, she had to be sent to a mental ward. To date, Amanda claims to be sober for three years and is currently studying fashion design and merchandising. With her troubled saga, it may be impossible to make a comeback.


Perhaps one of Disney’s most beloved talents who showed huge Hollywood potential was Lindsay Lohan. With her unforgettable roles in The Parent Trap, Freaky Friday and Mean Girls, she was on her way to becoming a real star—until the Hollywood lifestyle took a toll on her. LiLo went heavy on partying, causing her to be hospitalized numerous times for health problems. Consequently, her professional life suffered and she became a headache to Hollywood producers. It all went downward from there as her sporadic behavior caused her to rack up a laundry list of troubles including drug addiction, numerous DUIs, fights with the paparazzi, as well as odd, short-lived and sometimes violent romantic relationships. LiLo hasn’t been able to push any Hollywood project into fruition since her downfall.


When Shia LaBeouf starred in Transformers, he seemed to have triggered the Hollywood superstar radar. Top movie makers and viewers alike thought he had so much promise, with some even predicting him to be the industry’s next big thing. While his serious techniques as a method actor truly worked and produced great end results, it caused him to be a horrible workmate in movie sets. He even got on the nerves of superstar Brad Pitt whom he worked with in the 2014 film Fury. But his troubles aren’t exactly new. Since 2005, he’s been grabbing entertainment headlines for legal troubles such as trespassing, DUI, harassment, assault with a deadly weapon, disorderly conduct and even plagiarism. He was recently detained for rowdy behavior after passerby denied him a cigarette.


After appearing as Kevin McCallister in the 1990 monster-hit movie Home Alone, people had high hopes for him. But Macaulay Culkin became hooked on drugs at 15. Following bad movie role picks, his career saw a rapid descent with all of it happening before the public eye. Through the years, the world would see paparazzi shots of Mac dressed scruffily and just generally looking stick-thin and untidy. He would consciously turn down interviews despite him being in low-key, independent projects. His downfall became a hot topic for debates on how misguided superstar kids seem unable to handle all the fame and fortune that Hollywood brings. Even if he does some breakthrough career move, he will always be the industry’s poster child for a wasted Hollywood opportunity.

10. LIL’ KIM

In the ’90s, Lil’ Kim showed a lot of promise as a singer. She made music that was recognized by two top award-giving bodies, the MTV Video Music Awards and the Grammy Awards. She was still a hot music icon in the early 2000s, but all that went down the drain when she was indirectly involved in a 2001 shootout in Manhattan. Long story short, she lied to the court about the incident to protect her friends and paid the price: She was sentenced to jail. In the mid-2000s, Lil’ Kim tried to revive her career by appearing in shows and making more music, but she’s fallen so far from grace that the public doesn’t seem willing to reconsider. Her plastic surgery gone wrong is usually what makes the headlines nowadays.


The mere mention of Grey’s Anatomy has fans and followers of the show instantly thinking about and mentioning Katherine Heigl. The highly successful program paved the way for her to go mainstream and star in a few popular films. However, Katherine is notorious for her attitude problems that never fail to cause friction on the set. She is reportedly a nightmare to work with and isn’t exactly a PR darling. She even called her breakout movie Knocked Up “sexist” and had producers and co-stars fuming mad. While she seems like a beautiful woman who could do justice to big Hollywood roles, producers reportedly take her as a second choice. And while she recently took the lead role in the now-defunct NBC show State Of Affairs, Katherine becoming an A-list celebrity again is something most people seriously doubt.


When Tiger Woods turned professional in 1996, golf was never the same. The 14-time champion who racked up billions in total earnings as a celebrity athlete and endorser successfully made history in many aspects of the sport. But just as everything was looking up, it seemed Tiger couldn’t cope with the model-athlete expectations. In 2009, he was caught in multiple extramarital affair issues that led to his divorce. Over the years, he has been arrested for reckless driving and DUI while also suffering several injuries and health issues. With a very public troubled personal life and winless matches that dropped him to his all-time low professional ranking, it didn’t take long for his multi-million endorsements to pull out. He’s apparently “itching to get back out here,” according to his camp.


One of the most successful country singers of her generation, LeAnn Rimes was a force to be reckoned with at age 13. She became a household name as a talented crooner and landed a few TV and movie stints. However, all of her glorious work seemed to have faded into oblivion because of her scandalous hookup with now-husband Eddie Cibrian. LeAnn was married at the time of the affair and so was Eddie—who also had two kids with his wife. It turned out that LeAnn, whom many call a homewrecker, wasn’t the type to stay quiet. She was (and still is) constantly on social media fighting with complete strangers and Eddie’s ex-wife Brandi Glanville. Her recent album, which spoke of her affair with Eddie, was a flop.


Demi Moore was practically the royalty of the ’80s and ’90s Hollywood. Despite tough luck with several men including Bruce Willis, she certainly made a mark as a serious actress in several important movies. It seemed there was no stopping her from becoming a real success—until she consciously went on hiatus after a public affair and subsequent marriage to Ashton Kutcher who was 16 years her junior. After their public split in 2011, Moore’s personal life was reportedly in the dumps, with the actress displaying erratic behavior. She also dealt with substance issues and eating disorders that sent her hospitalized for months and made her the subject of a death hoax. Demi is currently taking on movie and television projects but many doubt she could make a brilliant comeback.


The modeling world is all about beauty and glam—but models aren’t always as flawless and angelic on the inside as they appear on the outside. Such is the case of Naomi Campbell—she was among the best in the industry but all that glorious reputation crumbled when she showed her true colors: She has really bad, violent temper. She became known for punching, kicking, slapping and physically attacking PAs, housemaids and photographers; causing public disturbance to a former boyfriend’s home; and countless incidents of her throwing fits when her demands were not met. Despite her substance addiction, the 47-year-old model is still around with a few industry projects here and there. But despite attempts, Naomi was unable to bounce back and fix her reputation as a real supermodel icon.


Despite the good looks and decent acting skills that made him a household name, Charlie Sheen couldn’t come close to being a superstar. The Hollywood bad boy’s timeline with trouble includes violent altercations with ex-girlfriends, ex-wives and even random prostitutes whom he had accidentally shot, beaten or abused. He had been in jail or received restraining orders for some of those charges. Charlie was also on a tax evasion trial and was caught several times abusing drugs and alcohol. While on the hit show Two and A Half Men in 2010 where he was earning millions, Charlie voluntarily checked into rehab. The icing on the cake was his admission in 2015 that he was HIV positive. After all that’s happened, he’s definitely not making a successful comeback.


The popular 2003 Fox series The O.C. skyrocketed Mischa Barton to fame. Her role as Marissa Cooper stuck with viewers, despite many detractors only thinking of her as a talentless pretty girl. While she had a huge following, Mischa saw her role killed off during the program’s third season. The main reason? She wasn’t the nicest person to work with, as confirmed by a fashion show she was in years later. In 2009, she was reportedly confined in the psychiatric ward for “suicidal actions.” She also had a DUI arrest and a fight with the paparazzi for plastering unflattering images of her all over the tabloids. Despite her troubled personal life, Mischa has had a few projects that keep her busy, but her star quality is done for good.


As a teen star, Edward Furlong had legions of followers who are now wondering what happened to him. The 39-year-old became an instant star after landing the iconic role of young John Connor in Terminator 2 back in 1991. Instead of becoming a successful star, everything was lost thanks to his poor life choices. Edward was suspected of a drug overdose in 2001, and ended up being arrested for DUI not long after. He has been in an out of rehab for substance abuse. Edward has a son but is divorced from his wife who accused him of domestic violence. That landed him in a mental facility in Los Angeles. Edward has attempted to star in various projects but none has allowed for his huge comeback.


The ’80s was Hollywood heaven for Val Kilmer. His killer looks and good acting landed him major roles that catapulted him to worldwide fame and lots of fortune. But Val’s real personality behind-the-scenes is widely known for being a major disappointment. He is reportedly a pretty demanding actor who would successfully manage to make an enemy out of anyone on the set. The Top Gun and Batman Forever star is reportedly a cranky fellow who would treat the crew badly or walk off in the middle of filming. Worse, he is reputed for his wild antics in interviews that didn’t help his image. His ex-wives could go on and on about his bizarre behavior and meltdowns, too, causing people to think he was somehow suffering from “insanity.” The result: He isn’t aging gracefully and his career has spiraled uncontrollably.

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