Top 20 Celebrities Who LOST EVERYTHING

It's cost you what, about two and a half million dollars already? It's cost me everything I've ever made. Welcome to WatchMojo, and today we're counting down our picks for the top 20 celebrities who lost everything. He had to give us $15,000 a piece to go and foul. Bankruptcy. Bankruptcy, to go broke. That's ridiculous. He couldn't even afford to go broke. For this list, we'll be looking at once successful celebrities who went from riches to rags. Which of these cases do you think is the most tragic? Let us know in the comments. Number 20. Heidi Montag Heidi Montag was only 19 when she joined the cast of the MTV reality show The Hills. What are your goals? Well, I want to do PR. That's like my ultimate goal. I want to be like the fun party PR girl in LA type of thing. So that's kind of what I want to do. At one point, the Colorado-born star was earning a six-figure salary per episode, alongside her future husband, Spencer Pratt, who she also met on the show. Montag and Pratt were worth a combined $10 million. But that all went down the hills due to their extravagant lifestyle. Every single night, we were taking 10 people to Wolfgang's Cut in Beverly Hills and ordering $3,000 bottles of Screamin' Eagle. And I would get like one sip because there would be like 10 people at the table. And I'd be like, we got to get another bottle so I can get another sip. We took our friends on vacations. You know, we're very generous with our money. The couple admittedly spent thousands on mindless shopping sprees and made questionable financial decisions that blew away their wealth. It got so bad that they had to vacate their home and move into Pratt's parents' house. Luckily, things seemed to be looking up, as Montag has made significant changes to their lifestyle and curbed unnecessary spending. Where do you see us in 10 years, Spence? Selling a lot of crystals to maintain our lifestyle. Number 19. Sly Stone Sly Stone rose to prominence in the late 1960s as the frontman and bandleader of Sly and the Family Stone. The group was groundbreaking, not only for their unique blend of funk, rock, soul, and gospel, but also for their racially and gender-diverse lineup. Stone's visionary talents led the group to commercial fame, but his struggle with substance use disorder largely contributed to their dissolution in 1975. In the years following that, Stone launched a solo career that never quite took off. What was the one or two reasons that caused you to be tired of being retired? I mean, that's everybody's dream to just, you know. Well, I needed attention and money, and I needed to do songs. On top of that, the substance use persisted, and he reportedly clashed with his manager and lost access to royalty payments for many years. This apparently put him in the hole, leaving him homeless and dependent on welfare checks. Number 18. Doug Hutchison Although he had accumulated a string of supporting film credits, Doug Hutchison's breakthrough came in 1999's The Green Mile. I just want to be out front is all. Come on, one time. And then you know what? You be rid of me. Hutchison earned critical acclaim and multiple award nominations for his performance as a sadistic prison guard in the Stephen King adaptation. He eventually lost all of that favor when, at the age of 51, he got married to the then-underaged, upcoming singer Courtney Stodden. Why the rush to get married? Because, you know, I felt like, um, this world isn't gonna last forever. And, uh, you know, life's short. Hutchison was widely criticized for the move and, according to him, was completely blacklisted by Hollywood and even his own family. This brought his once-flourishing career to a screeching halt, leading him to file for bankruptcy in 2017. The couple managed to weather the storm and remained together for years, although they eventually called it quits in 2020. It's been the rock for me through so many things, you know, that I've been through. So, um, you know, it's, it's, it's been, it's been interesting. Number 17. Teresa Giudice Since 2009, Teresa Giudice has been a regular cast member on The Real Housewives of New Jersey. That same year, Giudice and her husband Joe filed for bankruptcy, citing over $8 million in liabilities. This, however, was only the start of their troubles. In 2013, they were both indicted on multiple fraud charges, with some of them related to their 2009 bankruptcy case. What did you know about any of that? I would love to answer all your questions, and one day I will, but, you know, out of the respect of the process, I'm gonna let, you know, the legal matters play out in court. They eventually entered a guilty plea and were ordered to pay over $400,000 in restitution as a result. Giudice was sentenced to 15 months in prison, which she served at the Federal Correctional Institution in Connecticut. In 2020, Giudice filed for divorce from Joe, and the couple sold off their long-time New Jersey mansion the following year. How do you make a marriage like that work? I mean, it's kind of hard. Like, I want to wake up with someone, go to sleep with, you know, with some, you know, I want to wake up, you know, I want to spend every day with that person. Number 16. Kelly Rutherford Kelly Rutherford has been a staple on the small screen from as far back as the late 80s. The Kentucky-born actress first burst onto the scene with the NBC soap opera Generations. I want to thank you for making my dad's wish come true. You know, I am so glad he has you for a friend. Oh, honey, thank you for your support. She later gained further recognition with major roles in Melrose Place and Gossip Girl. But all of the money Rutherford amassed from those shows was eventually whittled away by a grueling custody dispute with her ex-husband, Daniel Garish. After filing for divorce in 2008, Rutherford fought for sole rights of their two children, a battle that cost her about $1.5 million in legal fees alone. As a result, she filed for bankruptcy in 2013. Regardless, the dispute continued, and Rutherford ultimately lost custody of both children in 2015. From the beginning, I said I would fight for my children. I think most parents would. This was a mother refusing to abide by a court order and forcing the father to do something that he was loath to do. With four Billboard number one hits, multiple awards, and tens of millions of records sold, TLC were undeniable powerhouses throughout the 90s. Their sophomore album, Crazy Sexy Cool, was released in November 1994, and sold more than 15 million copies worldwide. So it came as an absolute shocker when, the very next year, it was announced that they were filing for bankruptcy. TLC cited their seemingly exploitative record contracts, which left each lady with less than $50,000 in annual payments. At the height of their fame, they filed for bankruptcy, cheated, they say, by unfair recording contracts. They succeeded in renegotiating their contracts, and bounced back with 1999's Fan Mail. However, due to the sad and untimely death of Lisa Left Eye Lopez in 2002, they went on a hiatus, but have since come back together, now as a duo. Brett Butler For five years, Brett Butler played the titular divorced single mother on the ABC sitcom Grace Under Fire. How come I go to sleep when I'm not tired? Because whether you're tired or not has nothing to do with it, honey. You go to bed when mama's tired. As the main star, Butler took home around $250,000 per episode, but her struggles with substance use disorder eventually contributed to the series getting the axe in 1998. Since then, Butler has come under financial fire, admittedly making careless decisions that ate up most of her net worth. This is so dramatic, but I felt like my soul was leaving before. I knew I was probably gonna die. It wasn't what it should have been, which is losing my terrific husband, getting fired. Although she made a return to the small screen, taking up recurring roles in How to Get Away with Murder and The Walking Dead, things don't seem to have gotten any better. In 2021, Butler became so broke that she nearly lost her apartment, and hesitantly set up a GoFundMe page in order to save it. Number 13. Sinbad Comedian and actor Sinbad first gained popularity on the TV series A Different World, before landing his own sitcom, The Sinbad Show. Come on, man. We're a team, right, man? Always been a team. When something good happened to me, something good happened to you, right? Team, brother. Don't leave me hanging, brother. Come on. Although the series was canceled after one season, Sinbad went on to film multiple stand-up specials and appeared in a host of movies and TV shows. But as his star power kept rising, so did his spending, up to the point that it exceeded his income. And it certainly didn't help that he kept defaulting on his tax payments, ultimately accruing a tax debt of $2.5 million. In 2013, Sinbad filed for bankruptcy, declaring that he was $11 million in the hole, with only $16,000 in monthly income. I hate to say it, but when the bankruptcy hit me, people looked at me like, look at you. I said, bro, look at my life. You can look at me. You ain't never seen Sinbad with something that he wasn't supposed to have. I helped a lot of people in my life. I pushed a lot of people forward in my life. Number 12. Amanda Bynes Amanda Bynes spent four years on the Nickelodeon sketch series All That, before landing her own spinoff, The Amanda Show. Hello, I am Judge Trudy. Now, uh… Sure do, Judge Trudy. His complaint is ridiculous. Did I tell you it was your turn to speak, Misha? By the 2000s, she was already a teen idol, racking up credits like What a Girl Wants and Hairspray. But things soon took a downturn. Bynes faced a tough battle with substance use disorder, and found herself in a rabbit hole of legal trouble. With rules drying up and so many court cases piling, it became easy for money to go down the drain. Then she started making headlines for all the wrong reasons. A series of driving violations, disturbing tweets, even a hospitalization under a psychiatric hold. Even worse, she was placed under a conservatorship and lost control of her finances. Bynes seems to be getting her life back on track, however, as she has maintained a long streak of sobriety, and had her conservatorship ended in 2022. Number 11. Gary Coleman For his role as Arnold Jackson on the NBC sitcom Different Strokes, Gary Coleman was, at one time, receiving the biggest salary for any child actor on the small screen. Get a load of Super Mouse. Watch it, Vernon. The last dude who talked to me like that, I laserized his nose. But after Different Strokes came to an end in 1986, Coleman realized that his parents, who had been overseeing his finances, had grossly mismanaged it. In 1989, he filed a lawsuit against them, as well as a financial advisor, and was awarded $1.28 million in restitution. In the end, when he went to court to compel that accounting, he found that after everyone else was paid, there was almost nothing left for him. You were fleeced. Pretty much. However, the rules seemed to dry up as Coleman grew older, leading him to file for bankruptcy in 1999. He reportedly battled with multiple health and legal issues later in life, and passed away in 2010 after falling down and suffering a brain bleed. I just hope Gary's happy and, you know, he's in a better place and he's not suffering anymore. Number 10. M.C. Hammer Over the span of a decade, M.C. Hammer became the quintessential rags-to-riches and back-to-rags Hollywood story. After releasing two moderately successful albums, Hammer achieved worldwide fame with his hit single You Can't Touch This from his third studio album. At the time, Hammer's net worth was valued at over $33 million by Forbes. This seemingly overnight wealth was soon sucked up by his lavish spending, extravagant mansion, and numerous dependents. Everybody knew that I had 200 employees. It wasn't no secret. So what'd you think? I was paying them in hamburgers? By 1996, Hammer's musical success had plummeted, and he had to file for Chapter 11 bankruptcy as he was over $13 million in debt. The California rapper never quite recovered from his fall, despite a few comeback attempts. Number 9. Dennis Rodman As a professional basketball player, Dennis Rodman became world famous for his insane skills on the court, as well as his controversial persona. Rodman retired from the NBA in 2006, and also performed as a wrestler, actor, and reality TV star. Rodman's journey to penury began in the mid-2000s, when he became involved with the con woman Peggy Ann Fulford. Fulford posed as a financial advisor and was able to scam Rodman, as well as multiple other athletes, of millions. This ate into his finances so much, that he could barely afford to make his child and spousal support payments. After Fulford was convicted, Rodman was awarded over $1 million in restitution, which admittedly he most likely will never get. Number 8. T-Pain Since bursting onto the scene in 2005, T-Pain has racked up a slew of hit singles, and accumulated a fortune of over $40 million. However, instead of making wise financial investments, he bought a massive house and a $2.1 million Bugatti, which he later sold off for just $800,000. It certainly didn't take too long for that bank account to go low, low, low. By 2019, the Bayou a Drank singer was left with no option but to file for bankruptcy protection. He did win the first season of The Masked Singer the same year, and things seem to be looking up for T-Pain nowadays. Number 7. Todd Herzog Prior to being cast on the 15th season of Survivor, Todd Herzog traveled across America as a flight attendant for SkyWest Airlines. His highly calculated run on the show culminated in him winning the season and taking home the $1 million cash prize at just 22 years old. But while he triumphed on the screen, Herzog's entire fortune was in jeopardy, as he was struggling with alcohol use disorder. After seeking professional help, Herzog was able to turn his life around. He has since attained sobriety, and now lives a rather quiet life with his husband, Jess Hermanson. Number 6. Fantasia This North Carolina singer and actress was propelled to stardom after winning the third season of American Idol in 2004. Her first ever single, I Believe, went straight to number one in the U.S. and Canada, and her debut album was certified platinum. Things seemed to be off to a good start for Fantasia, but due to her sole breadwinner status among her siblings, mother and daughter, and the declining sales of her second album, she soon found herself struggling. Her $1.1 million house was set to be auctioned off to cover an unpaid loan. In an interview with Oprah, Fantasia owned up to her mistakes, blaming her misfortune on her financial decisions and inability to say no. In 2023, she announced her return to school after dropping out as a teen. Number 5. Gary Busey Once upon a time, Gary Busey was a mainstream Hollywood star. The Texas actor gained national attention for his leading performance in the 1978 biofilm The Buddy Holly Story, which earned him an Oscar nomination. He followed this up with starring roles in movies like Lethal Weapon and Point Break, which were certified box office hits. Listen, you snot-nosed little ----, I was taking shrapnel and quesad while you were crapping in your hands and rubbing it on your face! His financial downturn came in 1988, when Busey was involved in a serious motorcycle accident that left him with permanent brain damage. The once bankable Hollywood player became erratic on and off camera, and soon struggled to find roles in movies and TV shows. With most of his money gone and not enough coming in, Busey had to file for Chapter 7 bankruptcy in 2012. Number 4. Lil' Kim Widely regarded as the queen of rap, Lil' Kim inspired a generation of rappers with her music and has sold upwards of 30 million singles globally. Life really was all about the Benjamins for the hip-hop star. However, following dwindling album sales and a prison stint in 2005, Lil' Kim found herself in a free fall. In 2018, she declared bankruptcy, claiming to be about $4 million in debt, with unpaid taxes and mortgage loans taking up a large chunk of that figure. In order to pay off her debt, the Queen B's $2.3 million mansion was auctioned off, with the opening bid being $100. Yep, you heard that right. Number 3. Kim Basinger Kim Basinger became a Hollywood fixture for her notable femme fatale roles throughout the 80s and 90s. But at the height of her acting career, Basinger faced multiple setbacks that severely impacted her finances. First, she paid $20 million to acquire a small town in her home state of Georgia, an investment that backfired tremendously. Next, she backed out of the doomed movie Boxing Helena, for which she was sued and forced to pay millions of dollars to the studio. This resulted in her filing for bankruptcy. To top it all off, her marriage to Alec Baldwin ended in a messy divorce that reportedly cost the Oscar-winning actress another few million dollars. She never quite recovered financially. Number 2. Toni Braxton For someone like Toni Braxton, who's sold more than 70 million records worldwide, it's hard to imagine how she could go bankrupt twice. Just two years after her smash hit, Unbreak My Heart, Braxton found herself in dire straits. And had to declare bankruptcy. While her music generated millions, Braxton barely got any of it due to specific clauses in her recording contract. She managed to dig herself out of that hole, but ended up filing for bankruptcy again in 2010 after her Vegas residency was canceled due to her health issues. But just like the Phoenix, she was able to rise from her financial ashes, and has since produced and starred in the successful reality series, Braxton Family Values. Before we continue, be sure to subscribe to our channel and ring the bell to get notified about our latest videos. You have the option to be notified for occasional videos or all of them. If you're on your phone, make sure you go into your settings and switch on notifications. Number 1. Burt Reynolds Hollywood legend Burt Reynolds was a top box office draw in the late 70s and early 80s, but he gradually lost his bankability as the years progressed. This, coupled with his costly divorce from Lonnie Anderson and some poor investment choices, led to the actor filing for bankruptcy in 1996. He made a career comeback soon after with Boogie Nights in 1997, which earned him a Golden Globe and an Oscar nomination. By 2014, Reynolds was auctioning personal items and memorabilia, which rekindled news of bankruptcy. Until his death in 2018, Reynolds lived at his Florida estate, which once faced foreclosure, but was then bought by his neighbor, who let him live on the property at a low cost.