Top 20 Celebrities Who LOST EVERYTHING

Top 20 Celebrities Who LOST EVERYTHING

Welcome to WatchMojo, and today we’re counting down our picks for the Top 20 Celebrities Who LOST EVERYTHING.

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!

#20: Heidi Montag

Heidi Montag was only 19 when she joined the cast of the MTV reality show “The Hills”. 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 lifestyles. 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 seem to be looking up, as Montag has made significant changes to their lifestyle and curbed unnecessary spending.

#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 drug addiction largely contributed to their dissolution in 1975. In the years following that, Stone launched a solo career that never quite took off. On top of that, the substance abuse 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.

#18: Doug Hutchison

Although he had accumulated a string of supporting film credits, Doug Hutchison’s breakthrough came in 1999’s “The Green Mile”. 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 then underage, upcoming singer Courtney Stodden. 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.

#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. 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 longtime New Jersey mansion the following year.

#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”. 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 Giersch. 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.

#15: TLC

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 “CrazySexyCool” 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. They succeeded in renegotiating their contracts and bounced back with 1999’s “Fanmail”. However, due to the sad and untimely death of Lisa “Left Eye” Lopes in 2002, they went on a hiatus but have since come back together, now as a duo.

#14: Brett Butler

For five years Brett Butler played the titular divorced single mother on the ABC sitcom “Grace Under Fire”. As the main star, Butler took home around $250,000 per episode. But her struggle with substance abuse eventually contributed to the series getting the ax in 1998. Since then, Butler has come under financial fire, admittedly making careless decisions that ate up most of her net worth. 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.

#13: Sinbad

Comedian and actor Sinbad first gained popularity on the TV series “A Different World” before landing his own sitcom “The Sinbad Show”. 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.

#12: Amanda Bynes

Amanda Bynes spent four years on the Nickelodeon sketch series “All That” before landing her own spin-off “The Amanda Show”. 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 roles drying up and so many court cases piling, it became easy for money to go down the drain. 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.

#11: Gary Coleman

For his role as Arnold Jackson on the NBC sitcom “Diff'rent Strokes,” Gary Coleman was, at one time, receiving the biggest salary for any child actor on the small screen. But after “Diff'rent 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. However, the roles 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.

#10: MC Hammer

Over the span of a decade, MC 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 “U 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. 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.

#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 conwoman 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.

#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 $800K. It certainly didn’t take too long for that bank account to go “low low low.” By 2019, the “Buy You 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.

#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 Hermansen.

#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.

#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 bio film “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. 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.

#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 Bee’s $2.3 million mansion was auctioned off, with the opening bid being $100. Yep, you heard that right.

#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.

#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 “Un-Break 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.”

#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 Loni 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 off 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.