These Celebrities Faced Bankruptcy and Personal Ruin but Roared Back

Who doesn’t love a great comeback story? Whether it’s the Patriots roaring back against the Falcons in the Super Bowl or someone fighting tooth and nail to escape bankruptcy, we all enjoy a good redemption tale. It can be inspiring in our personal lives, too. Especially when we experience a career hiccup or are struggling with our finances, it can be comforting to know other people have gone through similar troubles — even celebrities.

If you keep an eye on the tabloids, you know even the rich and famous experience trouble with money. Or perhaps their careers fall apart due to addiction or illness. The point is celebrities are exposed to the same things us “normies” are. But that doesn’t mean they — or you — have to take it lying down.

A new project from GoCompare called There & Back Again tracks the up and downs, bankruptcies, and career derailments of 20 celebrities. It includes actors, sports stars, and musicians. And it might make you feel better about your own situation — especially because all of them were able to make a comeback after experiencing some sort of strife. We pulled 15 of the best stories to explore in further detail on the following pages.

Up first? This man famously saved the world from invading aliens — more than once.

1. Will Smith

Will Smith lives the opposite of a celebrity lifestyle in the movie Hancock

Actor Will Smith lives the opposite of a celebrity lifestyle in the movie Hancock. | Columbia Pictures

As hard as it might be to believe, there was a time when Will Smith found himself in serious financial trouble — bordering on bankruptcy. This was after he got his big break starring as the Fresh Prince and became an overnight success and a millionaire. But he was young and overlooked an important part of being an adult: paying taxes. The IRS sent him a bill for $2.8 million, and Smith saw his earnings evaporate. Within a few years, though, he was able to get out of debt and go on to become a bona fide movie star.

The Fresh Prince is only the beginning. You won’t believe the other big names who nearly lost it all at a young age.

2. Oprah Winfrey

Oprah Winfrey smiling

Oprah Winfrey | Mike Windle/Getty Images

  • The richest African-American woman in the world, Oprah Winfrey is worth more than $3 billion.

It’s hard to think of a more successful woman in modern America than Oprah Winfrey. Getting her start in local news, Winfrey has gone on to become one of the most powerful, successful, and richest women in the country. But things got off to a rocky start. Shortly after becoming an anchor in Baltimore at the age of 22, she was demoted — and all seemed lost. She fought her way back, though, and eventually moved to Chicago to start her empire.

One challenge Winfrey didn’t have to overcome? Marrying K-Fed.

3. Britney Spears

Britney Spears is in a silver dress on the red carpet.

Britney Spears at the 2015 ESPYS | Jason Merritt/Getty Images

  • At 10 years old, Britney Spears was as an understudy for an off-broadway play — alongside future star Natalie Portman.

While we might remember Britney Spears for her slew of hit songs in the late ’90s and early 2000s, it’s been up and down — way, way down — since then. In fact, it’s hard to think of a bigger career derailment in recent years. She famously suffered a breakdown, going to rehab, shaving her head and attacking paparazzi. She also lost custody of her kids. But she’s made a comeback lately and is performing at Planet Hollywood in Las Vegas weekly.

Another star who suffered a major career hiccup? The actor who would go on to play Iron Man.

4. Robert Downey Jr.

Rober Downey Jr. shows how to wear a boutonniere

Robert Downey Jr. | Kevin Winter/Getty Images

  • At the age of 5, Robert Downey Jr. made his film debut in the movie Pound.

For a while there, Robert Downey Jr. was completely off the radar. These days, he’s one of the biggest and richest movie stars in the world. But in his early 30s, after attaining some level of success, he went off the rails. He was arrested with guns and drugs and even spent time in jail. His struggles continued for a time, but he eventually turned it all around.

Next is a former E.T. star who experienced a roller coaster career.

5. Drew Barrymore

Drew Barrymore

Drew Barrymore | Alberto E. Rodriguez/Getty Images for Turner

  • Drew Barrymore was smoking at 9 years old and drinking by 11. At 12? Doing drugs.

You don’t often see people who have gone completely off track before becoming teenagers. Drew Barrymore is one of those rare examples. She attained stardom at a very young age and was then sucked into the Hollywood party scene. Barrymore even emancipated herself from her parents at 15 and got her own apartment. She did, however, go on to have a successful career despite those early setbacks.

Sports stars often have tumultuous careers, too.

6. Michael Jordan

Michael Jordan drives past Jeff Hornacek in the 1997 NBA Finals

Michael Jordan drives past Jeff Hornacek in the 1997 NBA Finals. | Vincent Laforet/AFP/Getty Images

  • Widely considered the best basketball player ever, Michael Jordan failed to make his high school varsity team.

We all remember Michael Jordan for leading the Chicago Bulls to an incredible championship run in the ’90s. But he took a mysterious and strange detour at the age of 30, right in the middle of it all, after being tied up in a gambling controversy and the murder of his father. He retired, briefly, and tried baseball. But he made a famous comeback and led the Bulls to more championships.

We go from the hardwood to the media for our next celebrity.

7. Larry King

Larry King sits as his desk on Larry King Line.

Larry King | CNN

  • His first broadcast was at the age of 24 — in 1957.

Larry King is a broadcast legend. He’s been on the air, in some form or another, for half a century. But early on, he found himself in debt and was accused of stealing thousands from a former business partner. He later declared bankruptcy with more than $300,000 in debt. He, like the rest of the celebrities on our list, roared back with his successful radio and TV shows — including Larry King Live, which was on CNN for 25 years.

Not many celebrities can credit a kitchen appliance to their success. But this next man can.

8. George Foreman

George Foreman is in a purple shirt and tie and dark jacket.

George Foreman | Dale de la Rey/AFP/Getty Images

How does one go from a world-famous boxer to a grill salesman? It’s a winding road. But it’s the road George Foreman took. His boxing career started in 1966 at the age of 18, and he eventually ended up losing to Muhammad Ali in the Rumble in the Jungle in 1974. This was the beginning of a troubled time for Foreman, who came close to bankruptcy. He returned to boxing and eventually inked a deal to sell those famous Foreman grills. Today, he’s worth more than $300 million.

Foreman put his name on a grill. Our next celebrity put his name on marijuana.

9. Willie Nelson

Willie Nelson

Musician Willie Nelson | Jason Davis/Getty Images for SiriusXM

Everybody knows who Willie Nelson is — as you’d expect for a man who has been recording music for roughly 60 years. But his career trajectory has had numerous twists and turns. He ran into financial woes with the IRS and later found more trouble after using illegal tax shelters. In the ’90s, he had his possessions seized and auctioned off to pay off $16.7 million he owed to the government. Eventually, though, he crawled back and erased his debts.

Now we go from the country scene back to Hollywood.

10. Kim Basinger

Actress Kim Basinger holds up her Oscar after winning the Best Supporting Actress

Actress Kim Basinger holds up her Oscar after winning the Best Supporting Actress. | Timothy Clary/AFP/Getty Images

  • Kim Basinger’s big break in Hollywood came when she landed the role of a Bond girl in Never Say Never Again.

Actress Kim Basinger isn’t a huge name like some of the others on this list, but she’s still an Oscar winner with a star on the Walk of Fame. It wasn’t easy getting there though. After starring in Batman in 1989, Basinger ran into trouble and lost more than $8 million (and filed for bankruptcy) after a lawsuit against a production company. She returned strong, winning an Oscar for her role in L.A. Confidential.

You might be wondering how much you can possibly earn playing the drums. Travis Barker will shatter your expectations.

11. Travis Barker

Drummer Travis Barker of the band Blink 182

Drummer Travis Barker of the band Blink-182 | Mike Coppola/Getty Images

  • Travis Barker’s net worth is estimated at $85 million.

How does a man go from drumming for the Aquabats to hoarding a fortune of $85 million? It’s pretty remarkable. Travis Barker joined Blink-182 in 1999, which launched his stardom with his two bandmates. The band would later go through a breakup, with Barker playing in numerous other groups. He went through a divorce, struggled with addiction, and even survived a plane crash. He turned it all around, though, with a return to Blink-182 and several other projects.

Moving on, how do you go from a cooking show to prison? This woman managed to do it.

12. Martha Stewart

Martha Stewart is talking on stage.

TV personality Martha Stewart | Daniel Boczarski/Getty Images

  • Martha Stewart’s sale of 3,928 shares in ImClone landed her a five-month jail sentence.

Most of us will remember Martha Stewart for her recipes and home goods. But her career took an unforeseen twist when she was sentenced to jail for insider trading in the early 2000s. She was actually America’s first self-made female billionaire. After her brief run-in with the law, Stewart recovered marvelously and can now be found hanging out with Snoop Dogg and adding to her fortune.

Next, meatloaf is hardly appetizing — except to your ears perhaps.

13. Meat Loaf


American pop singer Meat Loaf | Keystone/Getty Images

  • Meat Loaf’s real name? Michael Lee Aday.

The ups and downs have been in no short supply for Meat Loaf, the stage name for singer Michael Lee Aday. He started his first band at the age of 20 in 1967 and achieved fame and commercial success shortly thereafter. But trouble set in, with Meat Loaf struggling with addiction and mental illness and eventually filing for bankruptcy. The roller coaster ride continued for decades, but Meat Loaf has managed to make it back to the top.

Next up is another singer who has experienced wild ups and downs.

14. Cyndi Lauper

Singer-songwriter Cyndi Lauper performs onstage

Singer-songwriter Cyndi Lauper declared bankruptcy early in her career. | Larry Busacca/Getty Images for Songwriters Hall Of Fame

Cyndi Lauper’s biggest career hiccup happened early. In the early ’80s, Lauper filed for bankruptcy after her band’s manager sued them for firing him. They bounced back, recording hit songs, such as “Girls Want to Have Fun” and “Time After Time.” There were a couple more bumps in the road for Lauper, but overall she’s been able to overcome early financial difficulty to achieve success.

We’ll end with a celebrity who hit rock bottom with an arrest for shoplifting.

15. Winona Ryder

Actress Winona Ryder

Actress Winona Ryder | Chelsea Lauren/Getty Images

  • Winona Ryder’s big break came with the release of the movie Beetlejuice.

If there’s one thing many people will remember Winona Ryder for, it’s her big mistake in 2001. She was caught trying to steal $5,500 worth of merchandise from Saks, along with possession of prescription drugs. It was a setback, but she bounced back. Ryder has a star on the Walk of Fame and is currently starring in Netflix’s hit show Stranger Things.

See the complete project at GoCompare.

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