Years ago, Nicolas Cage was one of the highest-paid actors in Hollywood. However, he spent much of his fortune on wild purchases, including a $150,000 octopus and a $276,000 dinosaur skull (which he ended up returning to the Mongolian government because it turned out to be stolen). At one point, he owned 15 homes around the world, including two European castles. Eventually, he owed the IRS $6.3 million and faced foreclosures on multiple properties.

1

In an episode of 60 Minutes, Nicolas said that he threw himself into his acting to pay it all off: "Work was always my guardian angel. It may not have been blue-chip, but it was still work. Even if the movie ultimately is crummy ... I’m not phoning it in. I care, every time." The actor was able to settle his debts without declaring bankruptcy.

On an episode of The Breakfast Club, T-Pain recalled being "mega-rich," losing it all, and then becoming wealthy again. The singer once had $40 million in the bank, but bad real estate investments and poor spending decisions — like buying a Bugatti and returning it five months later for $400,000 less than he paid — left him broke. "I had to borrow money to get my kids Burger King," he said.

2

He explained that at this point in his life, he's no longer chasing the money. "That $40 million — I was hustling, I needed to be on everybody's record and every record gotta go No. 1, I gotta do this work. And at that time, I didn't know my family at all." He commended his wife for sticking with him through thick and thin and said his focus is now on his family.

After becoming a household name with The Parent Trap, Lindsay Lohan catapulted to teen idol with hits like Freaky Friday and Mean Girls. Then her career suffered as she dealt with years of legal trouble and personal issues. According to Refinery29, her net worth peaked at about $28 million but tumbled during this tough period of her life. Now the actor is in her comeback era: She recently cameoed in the new Mean Girls movie and starred in the Netflix rom-com Irish Wish.

3

With songs like "Un-Break My Heart," Toni Braxton is one of the best-selling female musical artists in history. But she filed for bankruptcy twice, telling ABC News that it was partially due to the setup of the music industry. Apparently, she only received a $1,972 royalty check from her first recording contract. However, she admitted having a serious home decor obsession: "I love dishes and house things, so I kind of lost it a little bit on the houseware." She said she lost touch with reality while indulging in the "girly things."

4

Heidi Montag and Spencer Pratt shot to stardom on MTV's The Hills. At the height of their fame, they brought in $2 million per year, according to People magazine. However, the couple also spent lavishly: $1 million on clothing for Heidi, another $1 million on a crystal collection for Spencer, and expensive dinners with $3,000 bottles of wine. "We were keeping up with the Joneses, but we were going against Tom Cruise and Katie Holmes," Spencer said. "We should have stayed in our reality TV lane."

5

The pair ended up moving into Spencer's parents' vacation home, where they lived rent-free and focused on their budget. He shared that they hadn't gone out for an expensive dinner since their anniversary. "Life is so short," Heidi said. "And what matters is being happy with family and marriage and with personal progress. We’re in a really good place."

In 2009, Stephen Baldwin — Hailey Bieber's father — filed for bankruptcy. According to ABC News, he reportedly owed $2 million between his house, credit card debt, and taxes. In 2013, he pleaded guilty to failing to file his taxes for three consecutive years and agreed to pay $300,000 in back taxes.

6

After the wild popularity of "U Can't Touch This," Forbes, per CNN, estimated MC Hammer's income in 1990 at $33 million. But he enjoyed an extravagant lifestyle and built a custom mansion on 12.5 acres with two swimming pools, a nine-car garage, four dishwashers, and a rehearsal hall. He filed for bankruptcy in 1996 with debts totaling at least $10 million.

7

Despite being one of the most successful country artists of all time, Willie Nelson found himself in deep trouble with the IRS for not paying taxes. In 1990, his property — including a golf course and recording studio — was seized across six states. The singer hilariously struck a deal with the government and recorded the album The IRS Tapes: Who’ll Buy My Memories to pay off his $16 million debt. While it didn't cover the full amount, it made a dent, and he paid it all off later.

8

Willie told Rolling Stone, "Mentally, it was a breeze. They didn’t bother me, they didn’t come out and confiscate anything other than that first day, and they didn’t show up at every gig and demand money. I appreciated that. And we teamed up and put out a record."

After gaining fame in Def Comedy Jam and Friday, Chris Tucker made the big bucks with the Rush Hour franchise; he earned $25 million for the third movie alone. But in 2021, he was sued by the IRS for $9.6 million in unpaid tax liabilities for the years 2002, 2006, 2008, and 2010. Last year, he reached a settlement deal and agreed to pay $3.6 million.

9

That wasn't his first run-in with the IRS. According to the Hollywood Reporter, he settled a $14 million bill with the IRS in 2014 after a lien was placed on one of his properties.

In 1989, Kim Basinger purchased Braselton, Georgia — a one-stoplight town with just 500 residents — for $20 million. She reportedly planned to revitalize the town and build a movie studio there. However, the actor backed out of a film she'd agreed to star in, and the studio sued her for breach of contract. When Kim was ordered to pay over $8 million, she filed for bankruptcy and later reached a settlement.

10

Without a doubt, 50 Cent was one of the biggest rappers of the 2000s. But after losing a multimillion-dollar lawsuit, he filed for bankruptcy in 2015 with $36 million in debts and assets of less than $20 million. In a 2020 interview with the Guardian, he said, "Businesspeople will do [bankruptcy] in a heartbeat before losing money. Because it means they have the ability to be secure and invest again." Apparently, bankruptcy gave him the ability to start fresh, paving the way for his hit show Power and a lucrative deal with a TV network.

11

Francis Ford Coppola is perhaps best known for directing the Godfather movies and Apocalypse Now, but he also directed the infamous 1982 film One From the Heart. He was so passionate about the project that his own production company financed it; however, it only earned about $600,000, compared with its $26 million budget. This led to deep financial trouble over the next decade, and he filed for bankruptcy three times.

12

And finally, Christy Carlson Romano was a Disney Channel star best known for Even Stevens. However, two years ago she posted a candid YouTube video about her financial journey. The actor recalled spending on shopping trips, expensive cars, and a psychic who "managed to get a lot of money from me." She continued, "I had this money at my disposal. I was never told how much money I was making. Money didn't have a purpose for me; I didn't really know what it was. I just knew that I had it and didn't care about it. That's a problem."

13