Funny Celebrities That Make a Lot of Money

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From Riches to Rags

From athletes and musicians to actors and socialites, celebrity usually coincides with massive wealth. However, there is no shortage of stars who find a way to squander even the most impressive fortunes. From lavish lifestyles to bad investments, these superstars found a way to lose it all, mostly on bigger purchases than more common wastes of money.

Related: Rich, Famous — and Cheap! 40 Frugal Celebrities

Johnny Depp

Wasted it on nearly everything
Johnny Depp's current troubles — charges of domestic abuse and being dropped as Grindelwald in the next film from the "Fantastic Beasts" franchise — might make him nostalgic for just a few years ago, when the actor was just entangled in a series of nasty lawsuits with former managers trying to assign blame for his financial ruin. Out of the mess came a window into Depp's outrageous spending. This included $30,000 a month on wine, $300,000 a month to maintain a 40-person staff, $150,000 a month for 24-hour security, $200,000 a month on private planes, and $3 million to blast journalistic legend Hunter S. Thompson's ashes out of a cannon.

Related: 19 of the Most Expensive Celebrity Divorces of All Time

Lindsay Lohan

Wasted it on a pricey London flat
Having recently signed a two-picture deal with Netflix, actor Lindsay Lohan was facing bankruptcy just a few years ago after failing to pay the rent on her 3.5 million pound ($4.6 million) London flat. The rent on the apartment was a whopping 78,000 pounds, which comes out to roughly $103,000.

Related: 22 Places to Hang Out Where You're Most Likely to See a Celebrity

Dionne Warwick

Wasted it on shopping
One of history's biggest hitmakers and the first female singer to launch a Metaverse Concert Series, Dionne Warwick has racked up five Grammys, sold more than 100 million albums, and earned $100,000 a month. But in 2013, she was down to her last $1,000, had amassed tens of thousands in credit card debt, and had a $10 million tax bill. She blamed her downfall on financial mismanagement — and a compulsive shopping habit.

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Wesley Snipes

Wasted it on an $8 million mansion (among other lavish purchases)
One of the most high-profile criminal tax evasion defendants in modern history, Wesley Snipes served time in federal prison for tax fraud. Part of his trouble came from following the advice of a shady anti-tax advocate, but another part was lavish spending. He bought an $8 million mansion in Alpine, New Jersey, an exclusive haven for rappers, athletes, and other new-money millionaires. These days he's back on screen with films such as "Dolemite Is My Name" and "Cut Throat City," both on Netflix, and "Coming 2 America."

Related: 27 Big Celebrities Who've Had Tax Trouble

Nicolas Cage

Wasted it on shrunken Pygmy heads, a dinosaur skull and a private island
Actor Nicolas Cage has never been short of work — he hosted the Netflix series "The History of Swear Words" last year — but at one point, he faced financial ruin after blowing $150 million on, among other things, a $150,000 pet octopus, 15 homes (including a bunch of giant mansions and two castles in Europe), his own island in the Bahamas, shrunken pygmy heads, and a quarter-million dollar dinosaur skull that he had to return after it was determined the fossil was stolen.

Related: 10 Opulent Castles You Can Buy for the Price of a Manhattan Condo

Allen Iverson

Wasted it on jewelry
Including endorsement deals, Philadelphia 76ers great Allen Iverson earned around $200 million over the course of his career. By 2012, however, he was broke. His lavish lifestyle included mansions and cars and, of course, jewelry. By the time he went bust, he owed $859,000 to a single jeweler.

Related: 30 Strange and Expensive Celeb Purchases

Stephen Baldwin

Wasted it on a high-end homeless crash pad
Baldwin brother Stephen of "The Usual Suspects" fame declared bankruptcy in 2009. At the time he was underwater on a New York property on which he still owed at least $2.3 million but was worth only $1.1 million. The born-again Christian had also opened his property to a homeless man who was later arrested as a suspected drug dealer.

Gary Busey

Wasted it on addiction
If you enjoyed "Gary Busey: Pet Judge" on Amazon Prime, you may wonder where the actor got his legal chops: After starring in more than 70 movies, Gary Busey was down to his last $50,000 by 2012, when he filed for Chapter 7 bankruptcy. He owed at least 10 times that amount to a laundry list of creditors and to the IRS. The notoriously eccentric "Point Break" star once admitted to an all-consuming cocaine addiction. Before going broke, he appeared on "Celebrity Rehab."

Chris Tucker

Wasted it on a collection of houses
In 2014, funnyman Chris Tucker faced a massive $14 million tax bill that swelled through years of nonpayment. The "Rush Hour" star still found plenty of money to buy houses one after another. In 2007, it was reported that Tucker bought his third home — a $6 million, 14,000-square-foot mansion.

Related: 32 of the Most Expensive Celebrity Homes of All Time

Burt Reynolds

Wasted it on a giant estate in Florida
In 1996, '80s Hollywood heartthrob Burt Reynolds declared bankruptcy after claiming to be $10 million in debt after losing his $40 million fortune. Facing foreclosure on his 4-acre estate, the actor tried to sell it for far more than it was worth in 2011 but found no takers. Reynolds died in 2018.

Related: 22 Celebrities Who Died Broke (or Close to It)

MC Hammer

Wasted it on payroll
Arguably the biggest name in music in the early '90s, MC Hammer earned $33 million by 1991. Five years later, it was all gone and Hammer was in debt to the tune of $13 million. One of his biggest expenditures were the hundreds of new best friends he found and "employed" once he got rich. At one point, the rapper's payroll exceeded $1 million a month.

Francis Ford Coppola

Wasted it on a musical flop
Francis Ford Coppola is known for "The Godfather" trilogy and other great films, but by 1992, the iconic director also laid claim to a trio of bankruptcies. They all stemmed from a massive 1982 investment in a costly musical called "One From the Heart," which was a huge, un-Coppola-like flop. With this long in the past, Coppola continues to produce — working on a movie now decades in the making called "Megalopolis" and releasing well-regarded wines.

Related: Celebs Who Own Beer, Wine, and Spirits Brands

Mike Tyson

Wasted it on exotic tigers
Any discussion about squandered celebrity fortunes must include Mike Tyson. He grew up in poverty, amassed a $300 million fortune, and blew it all. Among his most lavish and legendary expenditures were three white Bengal tigers, which cost hundreds of thousands to buy and train and $1,500 a day to feed. After a prison stint, Tyson has stayed out of trouble for many years now.

Related: 20 Outrageously Expensive Celebrity Purchases

Kim Basinger

Wasted it on a bad movie
Now famous as an animal-rights activist, Kim Basinger had among the hottest acting careers of the 1980s. Unfortunately, by 1993 the "Batman" star was embroiled in several ugly lawsuits that eventually drove her into bankruptcy. In a judgment that was eventually overturned, Basinger was ordered to pay $8 million for breaking an "oral contract" to appear in a movie called "Boxing Helena." (Of course, who can forget that in 1989 she spend $20 million to buy virtually the entire town of Braselton, Georgia, to turn it into a tourist attraction and film studio? She had to sell as part of her 1995 bankruptcy.)

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Curt Schilling

Wasted it on a video game company
Former Red Sox great pitcher lost $50 million on an investment in a video game company called 38 Studios. He was a better player than an entrepreneur, it turns out. The company went bust and Kingdoms of Amalur: Reckoning did not revolutionize the Massive Multiplayer Online market. Since then he's specialized in controversial social media posts — including tweeting support for the Jan. 6 attack on the U.S. Capitol — and being rejected for the Baseball Hall of Fame 10 times.

Toni Braxton

Wasted it on mansion addiction
In 2010, "Unbreak My Heart" singer Toni Braxton filed for bankruptcy after racking up $50 million in debt, including money owed on a lavish mansion she could no longer afford. Four years later in 2014, her settlement was complete, but the singer apparently hadn't learned her lesson; just six months later she plunked down $3 million on a new estate. Maybe now she can afford such things again? She released an album in 2020 and stars in the "Braxton Family Values" reality TV show, which is said to be coming back this year but it's unclear where it can be seen.

Warren Sapp

Wasted it on a lion skin rug (in a really big house)
In 2012, Tampa Bay Buccaneers Hall of Famer Warren Sapp joined the list of athletes who squandered a fortune on lavish purchases. Although he earned more than $82 million over the course of his career, Sapp had just $826.04 in his bank account by 2012, thanks to purchases such as 240 pairs of sneakers and a lion skin rug — both of which were housed in a 15,000-square-foot mansion. Based on his Instagram feed, he now leads a pretty pleasant life fishing and at sea with friends.

Related: The Most Expensive Sneakers Ever Sold at Auction

50 Cent

Wasted it on a 52-room mansion
In 2016, a judge approved a resolution for rapper 50 Cent's bankruptcy proceedings, which had been playing out in public for a year. His problems were mainly wrapped up in his house, whose previous inhabitants also all went bankrupt or even went to prison for bankruptcy fraud. The 50,000 square-foot Connecticut mansion had 52 rooms, nine kitchens, a basketball court, and a $70,000 monthly maintenance and upkeep fee. While 50 Cent still records and releases music, even appearing in the 2022 Super Bowl halftime show, his feuds and public actions also grab attention. His current beef with the network Starz, for which he executive produces "Power," "Power Book II: Ghost" and other projects, is his latest.

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Mekhi Phifer

Wasted it on guns and a leather bed
In 2014, "ER" and "8 Mile" star Mekhi Phifer — most recently on Hulu's "Love, Victor" — filed for bankruptcy, claiming debts of $1.3 million and assets of just $67,000. Part of his problem might have been his $7,500 monthly income and $11,600 monthly expenses; it also might have had something to do with high-end purchases such as his gun collection and a bed made of leather.

Antoine Walker

Wasted it on houses and cars
NBA star Antoine Walker earned $108 million over the course of his remarkable career. By 2010, he had nothing to show except a bankruptcy proceeding. His baller lifestyle included lavish expenditures on houses, cars and shiny things. He also took on legions of hangers-on who treated him as a human ATM machine.

Joe Francis

Wasted it on luxury cars
Talk about a footnote to history. "Girls Gone Wild" founder Joe Francis — who seemingly had as many legal troubles as sleazy VHS releases — was so broke by 2015 he was facing arrest for failing to surrender two luxury cars as ordered by a bankruptcy judge. By that time, Francis had been convicted of assault, owed over $10 million to casino magnate Steve Wynn, and was in trouble with the IRS. His final downfall, however, was the Bentley Flying Spur and Cadillac Escalade he allegedly tried to conceal. He's spent recent years at an estate in Mexico with his family.

Related: 16 Most Enviable Celebrity Car Collections

Sheryl Swoopes

Wasted it on bad investments
During her WNBA heyday, Sheryl Swoopes was the greatest women's basketball player in the world and had a $50 million fortune. After a series of bad investments, however, the first woman ever to get her own Nike shoe was so broke she had to sell her Olympic medals to pay an IRS debt.

Lenny Dykstra

Wasted it on a mega mansion
By 2011, former Mets and Phillies slugger Lenny Dykstra was facing prison time for charges that included bankruptcy fraud and identity theft. His $58 million fortune was squandered, and his $18.5 million mansion — which he bought from Wayne Gretzky — was in foreclosure. His wife and kids had left him, and his immediate family was also estranged. He served 6 1/2 months in prison.

Aaron Carter

Wasted it on a family compound
The kid brother of a Backstreet Boy, Aaron Carter was a pop star by the time he was 7 years old. When he grew up, however, he made a whole bunch of money mistakes and blew his fortune, which equaled $200 million, before his 18th birthday. Among his expenditures was a 12-home Carter family compound. His D-list celebrity life has led him some strange places, from criminal allegations against family to a fashion line, plans to box NBA star Lamar Odom, and racy, live appearances for fans online.

Michael Vick

Wasted it on a dog fighting ring
Lots of celebrity athletes go broke, but Michael Vick stands out for actually paying what he owed his creditors. Six years after filing Chapter 7 bankruptcy in 2008, Vick paid nearly the entire $18 million he owed after racking up debt in the wake of his downfall and incarceration for running an illegal dog fighting ring. He became a sports analyst for Fox.

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Source: https://blog.cheapism.com/celebrities-who-went-broke-18413/