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Mike Tyson

Widely regarded as one of the greatest boxers of the modern era, “Iron Mike” Tyson exploded onto the scene as a junior boxer in the early 1980s. He earned the WBC heavyweight champion title just four months after his 20th birthday, becoming the youngest boxer ever to reach that mark. He won an astonishing 26 out of 28 fights by knock out, an impressive feat in an increasingly safety-conscious boxing culture.

According to a comprehensive 2003 report by The New York Times, Tyson earned approximately $400 million during the first 18 years of his boxing career. But all the money in the world couldn’t help Tyson.

Out of the ring, his run-ins with the law, including a sexual assault conviction that landed him in prison for three years, were frequent and disturbing. In the ring, despite his early successes, he’s perhaps best remembered for the ill-fated 1997 comeback bout known as “The Bite Fight,” in which he bit opponent Evander Holyfield’s ear hard enough to draw blood — twice. Tyson finally declared personal bankruptcy in 2003, and has devoted his time since to rehabilitating his reputation.

What happened

Tyson raked in $30 million per fight at the peak of his career, but he bled money as readily as he earned it. In 2003, the Times called him “a cash machine to himself and others,” detailing lavish spending on “jewellery, mansions, cars, limousines, cellphones, parties, clothing, motorcycles, and Siberian tigers.” In December 2002, he bought a $173 000 gold chain on credit, adding it to the $27 million in debts listed in his 2003 bankruptcy filing.

Tyson’s largest debts included a $17,4 million in tax liabilities to US and British authorities, a $9 million divorce settlement with former wife Monica Turner, several million in obligations to a gaggle of lawyers and producers, and more than $300 000 to a limousine company. His largest assets included a Farmington, Connecticut mansion, soon sold to fund the divorce settlement, and two extravagant properties in Las Vegas.

At the time of his bankruptcy filing, Tyson was pursuing a $100 million lawsuit against boxing promoter Don King, who Tyson claimed bilked him out of millions of dollars in revenue. In 2004, he settled with King for $14 million, according to the Times — trimming, but not eliminating, his debts. Tyson did eventually exit bankruptcy after forfeiting much of his trove of physical assets and setting aside a substantial share of his future earnings to pay lien holders.

Post-bankruptcy activities

Far past his prime, Tyson continued boxing for several years after emerging from bankruptcy, most memorably in a 2006 “comeback” tour with a veteran boxer in even worse shape than he. Tyson also sought out endorsement relationships to help pay the bills. He found some success, though most major brands refused to be associated with him on account of his criminal history and uncouth image.

Tyson also pursued acting and music, making an extended self-cameo in the 2009 comedy hit “The Hangover” and starring in a Spike Lee-produced one-man show that hit 36 cities and culminated in an HBO special.

After a series of arrests, including for driving under the influence and fighting a reporter in Los Angeles International Airport, Tyson sought sobriety and calmed his personal life. In 2013, he released a best selling book, “Undisputed Truth,” and he guest-sang on a Madonna track two years later.

50 Cent

When he burst onto the hip-hop scene in the early 2000s, the former Curtis James Jackson III was heralded for his crossover appeal and obvious talent. And his personal story was captivating, to say the least. Raised in crime-ridden New York City neighbourhoods at the height of the crack epidemic, he sold drugs as a teenager and allegedly took nine bullets (though the true count is unclear, per BET) in a 2000 shooting that nearly killed him.

Over the course of his career, which continues despite diminishing returns, 50 Cent has sold more than 30 million albums and earned dozens of music awards, including a Grammy and 13 Billboard awards. At one point, he was the second-wealthiest hip hop artist in America, behind only Jay-Z.

Soon after the 2003 release of “Get Rich or Die Tryin’,” his first major-label album and most successful to date, Cent expanded into non-musical business ventures. In 2005, he headlined a successful, semi-autobiographical film named after his breakout album. He became an early investor in Glacéau, the maker of Vitaminwater, and reportedly earned $100 million when Coca-Cola bought the company in 2007.

His investment in G-Unit Films, a production company, was less successful, as was his founding investment in SMS Audio, which later faced accusations of copyright infringement for the design of its Street by 50 headphones. He was also briefly the subject of an SEC insider trading investigation and participated in a bizarre scheme to launch a line of 50 Cent-branded palladium in partnership with a South African precious metals mine.

What happened

50 Cent’s music sales steadily declined after peaking in the mid-2000s, along with his income. Despite scattered business successes, notably his Glacéau investment, Cent spent heavily on a lavish lifestyle featuring Rolls-Royce automobiles and the same Connecticut mansion that Mike Tyson lost a few years earlier.

Like many wealthy celebrities from impoverished backgrounds, he generously supported a small army of friends and family members, including his grandfather and a former long-time girlfriend. He also gave freely to worthy charitable causes, such as HIV treatment and prevention in Africa.

Cent suffered from self-inflicted wounds as well, according to HotNewHipHop. In an act of personal retribution, he publicly shared a sex tape featuring a rival rapper’s ex-girlfriend, and was eventually forced to pay $5 million to resolve the resultant lawsuit.

He also lost more than $2 million on Sleek by 50, another headphone venture, and was then hit with a more than $17 million judgment for allegedly stealing the design for that product. Though the exact extent of his losses and subsequent recoveries are unclear, he has publicly stated that he lost millions in the stock market during the 2008 financial crisis.

All told, Cent racked up more than $20 million in liabilities against assets of less than $15 million. In 2015, he declared bankruptcy in an effort to restructure and slim down these obligations, losing much of his fortune in the process. Notably, Cent was forced to part with his Farmington estate, following in Tyson’s illustrious footsteps.

Post-bankruptcy activities

The jury is still out on 50 Cent’s post-bankruptcy activities. As his musical career declined, Cent devoted more attention to film work, a trend that appears likely to continue.

 Nicolas Cage

Many people don’t realise Nicolas Cage is Hollywood royalty. He’s legendary director Francis Ford Coppola’s nephew, and is related by blood to several prominent actors and directors, including Sofia Coppola and Jason Schwartzman. In his telling, he changed his name to “Cage” as a young man to avoid the appearance of favouritism.

It worked. The prolific Cage found success in a string of romantic comedies through the 1980s, then switched to dramatic and action roles through the 1990s, doggedly earning his way onto the Hollywood A-list.

He pocketed an Academy Award for 1995’s “Leaving Las Vegas,” and was nominated for 2002’s “Adaptation,” though he racked up several Golden Raspberry “worst actor” awards in the years since.

Cage’s hard-charging approach to movie stardom earned him a lot of money — according to FinanceBuzz, he pocketed $150 million between 1996 (a decade after his career began) and 2011. During that time, he earned $20 million apiece for blockbusters like “Gone in 60 Seconds” and “National Treasure.” However, by 2009, much of Cage’s fortune had vanished in a hurricane of lavish spending, and the star faced mounting legal troubles that further added to his financial woes.

What happened

Starting in the 1990s, Cage embarked on a decade-long buying spree to rival Mike Tyson’s. According to Thrillist, his many bizarre and expensive purchases included:

• Several supercars, including a rare Ferrari and the Shah of Iran’s Lamborghini
• Rare jewellery
• A shark
• A crocodile
• Two king cobras
• At least one dinosaur skull
• A collection of pygmy shrunken heads
• A private jet
• A pyramid tombstone in a New Orleans cemetery

Cage also bought up and sold a slew of exotic real estate, including a 26-acre Rhode Island estate (then the most expensive home ever sold in the state); castles in England and Germany; a private island in the Bahamas; a “haunted” New Orleans mansion that purportedly saw a string of grisly murders in the 1800s; and a comic-strewn Southern California mansion described by the Los Angeles Times as “frat house bordello.”

Cage’s problems began in 2009, when the IRS filed a tax lien against his New Orleans home for millions of dollars in unpaid taxes dating back to the early 2000s.

They accelerated later that year, when former girlfriend (and mother to Cage’s oldest son) Christina Fulton sued him for $13 million and ownership of her house, then owned by Cage. Cage also faced multi-million-dollar collection attempts by at least two financial institutions, and was hit with a counter-lawsuit from business manager Samuel Levin, whom he’d earlier sued for fraud and negligence.

Ultimately, Cage lost his California home to foreclosure, though it failed to sell at a fire-sale foreclosure auction (perhaps on account of its questionable decor). He lost a smaller Nevada property to foreclosure too, and offloaded many of his exotic personal possessions in piecemeal fashion. Not quite bankruptcy — more like non-voluntary downsizing.

Post-downfall Activities

Nicolas Cage pieced his financial life back together the only way he knew how — by working his tail off. Between 2009 and 2016, he appeared in about two dozen movies, from actual hits such as “The Croods,” to critically panned failures such as “Drive Angry.” Low standards for films such as “Drive Angry” aside, Cage seemed to judge that humiliation was preferable to destitution.

And, in addition to steady film pay checks, Cage’s finances got a boost in 2011, when he sold a rare comic book for more than $2 million – approximately 20 times its 1997 purchase value, per CNN. — Moneycrashers.com