#20. Mekhi Phifer
Most people remember Mekhi Phifer from his role on E.R., the series created by Michael Crichton that used to be all the rage in the late 90s and early 2000s. Like Friends, which also became a massive success during the same era, E.R catapulted its actors to superstardom.
This was Mekhi Phifer's first huge break, and he continued to hit it big with his role on 8 Mile, the acclaimed semi-biopic movie that showed Eminem's tough past. Unfortunately, Phifer repeatedly purchased unnecessary items (from expensive firearms to bed 100% made out of leather!) and his debts led him to bankruptcy in 2014.
#19. MC Hammer
Stanley Kirk Burrell, aka MC Hammer, can boast some remarkable achievements: he was the first rapper to have a Diamond Certified Album (for sales of over 10 million copies) and he's widely regarded as one of the best dancers in hip-hop.
With his flashy clothes, exuberant moves, and catchy hits (like Can't Touch This) the artist enjoyed national popularity, and this success was reflected in his bank account: he earned over 30 million in only 2 years! But several luxury cars, a mansion, and a copyright suit later, he found himself owing 10 million!
#18. Lil Kim
It's well known that many celebrities go overboard with plastic surgeries and get caught in an addictive cycle of retouching their faces. To each their own, one could say. And sure, one's body is one's business, but it's undeniably sad to find out that a person is now unrecognizable because of the amount of cosmetic procedures.
Lil' Kim is maybe the prime example of this, there's nothing left of the charismatic rapper that used to wreak havoc in the music scene of the 90s in New York! Her financial situation has also suffered a downfall, unfortunately: the IRS is closely following Kim's steps due to her debt of 1 million.
#17. Francis Ford Coppola
During the 70s Francis Ford Coppola cemented himself as one of the best directors of his generation. That's right, classics like The Godfather, Apocalypse Now, Patton, and many others, confirmed over and over his legendary movie-maker status.
Even The Godfather's sequel earned him Academy Awards! The man was on fire during the 70s and 80s... so how did he end up owing almost 100 million dollars? Shockingly, one of his films plummeted his wealth. After spending 30 million form his own pocket for One from The Heart, a movie that turned out to be a complete failure, the director's economic situation went from bad to worse!
#16. Floyd Mayweather Jr.
However, a couple of solid projects helped the director bounce back from that dramatic mountain of debt. Floyd Mayweather shares a similar story, in some sense. Though the ex-boxer always seems to have problems with the IRS, he knows that in the worst-case scenario, his prestige will be there to save him.
His last couple of fights with Maidana and Pacquiao meant dozens of millions in revenue for the unbeaten champion who loves to show off his luxurious lifestyle on social media. However, Floyd is not very keen on playing by the rules of the IRS, and his enormous debt led him to fight McGregor to obtain a few extra millions, just in case.
#15. Lindsay Lohan
Justin Bieber, Macaulay Culkin, Lindsay Lohan, what these stars have in common? All of them rocketed to worldwide fame as young children. It's insane when you come to think about it! Imagine having millions of dollars at the age of 11.
Paparazzi following you everywhere, fans obsessed with your life... any kid would go crazy and spiral out of control. That's usually the case, and after the success of Parent Trap, Freaky Friday, and Mean Girls, Lohan's money started to go down the drain due to wild parties. Lindsay has lost most of her wealth, but she's sober and back to acting now.
#14. Johnny Depp
Johnny Depp has amassed a jaw-dropping fortune with his roles on box-office hits like The Pirates of The Caribbean, Charlie and The Chocolate Factory, Sweeney Todd, and The Tourist. So why does he owe more than 20 million?
It's a great question. According to him, his management company committed fraud behind his back. However, Depp does have a history of curious investments: yachts, a record label that would later fail completely... and the list goes on.
#13. Aaron Carter
If Aaron Carter's name rings a bell for you, but you're still not sure if you know who he is, then maybe it's because you're confusing him with his older brother Nick, from The Backstreet Boys.
Though Aaron was never an official member of the pop boyband, he did tour with them during their heyday and even achieved a successful solo career as a teen pop star himself. His first three albums went Platinum and he also appeared on the Broadway musical Seussical. That means a lot of money, but Aaron had a habit of evading taxes, and the IRS finally punished him for his wrongdoings.
#12. Vanilla Ice
Sometimes, when a catchy song is released by a musician, it can become a huge hit thanks to its crossover appeal, its funny video, a notable feature, or even because of a meme. A multi-platinum single is obviously great news for an artist, but long-term consistency is always needed to sustain a career.
If you don't believe me, ask Vanilla Ice, who can boast of having had put out one the most viral singles of the late 80s/early 90s with Ice Ice Baby. Though he obtained millions with the song, he never dropped a convincing album and people gradually lost interest in his work. A million-dollar-worth divorce was the final blow to the fortune that he once possessed.
#11. Willie Nelson
With memorable songs like Blue Eyes Crying in The Rain and You Were Always on My Mind, amongst countless others, Willie Nelson became one of country music's greatest legends in the 70s.
Though the 70s saw the activist and musician earn millions of dollars, his debt with the IRS increased rapidly in the 80s and the organization decided to confiscate his assets in 1990. Willie's solid career let him get on his feet again quickly, but he then had to auction many of his possessions and hand in the income of all the sales of a new album, which was suitably titled The IRS Tapes.
#10. Pamela Anderson
Maybe you weren't there to witness the Baywatch frenzy, but it you've watched Friends then you're probably familiar with this phenomenon. Like Joey and Chandler, many fans set their alarms at the exact time when the show started during the 90s.
Pamela's notorious role on this series turned her into an A-list celebrity and, albeit briefly, into America's biggest supermodel. Anderson quickly became a millionaire then, but her extravagant lifestyle couldn't be sustained when her fame (and income) started to slump.
#9. Mike Tyson
Pamela Anderson's second mistake was thinking that anyone can outsmart the IRS and get away with murder, and guess what? Mike Tyson made the same mistake. As well as the model and actress, the man who was once on the top of boxing ladder is still rich, but not even as half as rich as in his heyday.
The retired sportsman with one of the most iconic tattoos on Earth suffered and expensive divorce and wasted part of his fortune on head-scratching purchases, including two white tigers (believe me, these cost more than a couple grand), and that's why his fortune fell from half a billion dollars to about 5 million.
#8. Courtney Love
Courtney Love's rise from the punk underworld to rock superstardom accounts for one of the most wild and compelling from rags-to-riches stories in music. Though many grunge fans are not familiar with Hole's debut record, Live Through This (their 2nd LP) made a huge splash in the 90s rock scene.
With stomping songs like Violet and Miss World, the album, Courtney proved her band's haters wrong and became one of the most successful front-womans in rock history. However, interest in Love's music career began to diminish in the 2000s and this had a massive impact in her financial situation: by 2012 she owed 30 million to the IRS.
#7. Drake Bell
That's the problem with the careers of celebrities that enjoy an outstanding peak of success, but ultimately end up being a flash in the pan. If you're a musician, your audience may grow up and lose interest if the output is not consistent, if you're an actor, the series that propelled you to stardom may suddenly come to an end.
What's next when that happens? This is a question that Drake Bell probably asked himself at one point, after the cherished Nickelodeon sitcom Drake and Josh concluded after 4 seasons. Bell's confidence was through the roof, and he assumed that being successful in the music industry was a piece of cake for him. Things didn't go well for him, and he had to sell his mansion in 2014.
#6. Bow Wow
Though the self-esteem of some of the celebrities that appear on this list hit rock-bottom after realizing that their luxurious lifestyles was in the past and that the IRS never fails to catch up with you, they also rejoice at the fact that most of their fans are unaware of their financial troubles.
Indeed, many famous people love to show off their fancy lifestyle, even if what they're showing is fake. But Bow Wow couldn't believe his bad luck when a fan of his realized that this Instagram post that affirmed that the rapper was about to hop on a private jet was a complete smoke screen. The other man was sitting next to him on the tourist-class flight and uploaded the proof on Twitter for everyone amusement.
#5. Rupert Grint
Do you remember when we talked about the hardships of becoming a big celebrity at a young age? We cited Lindsay Lohan, Justin Bieber and Macaulay Culkin as examples, but the stars of the Harry Potter movies constitute other notorious cases.
But those 3 kids, who are now young adults, didn't share the same fate after those 8 movies. While Daniel Radcliffe and Emma Watson went on to achieve impressive acting careers (especially Emma), Rupert wasn't as lucky. To make things worse, he constantly tried to escape from the claws of the IRS, and he had to pay 1 million dollars to settle the score with them.
#4. 50 Cent
From protégé of Eminem and Dr. Dre to a hip-hop king on his own merit, Curtis Jackson aKa 50 Cent left a huge mark on the genre's history during the first half of the 2000s with a couple of significant gangsta-rap releases.
But after Curtis, his 3rd album (which came out in 2007) his acclaim began to diminish and 50 failed to adapt to the genre's shift in sound. He still had the fortune that he had gained from the sales of millions of records, but after losing a court case for 7 million and spending 15 million on a business that would prove to be a failure, Jackson had to file for bankruptcy in 2015 due to his debt.
#3. Lauryn Hill
Lauryn Hill first became a prominent figure in Rnb, Soul and Hip-Hop with The Fugees. Packed with mesmerizing songs like Killing Me Softly, the group's second studio album, titled The Score, instantly became an undisputed classic.
But Lauryn continued to enjoy her creative peak in the 90s during her solo career with The Miseducation of Lauryn Hill, one of the greatest albums of all time. However, after this amazing record she disappeared from the public eye and stopped releasing music due to the frustration that she felt towards the industry. Additionally, Lauryn stopped paying her taxes, and a couple of years later she had to pay 1 million dollars to the IRS.
#2. Tyga
Unlike Lauryn, Tyga’s habit of not paying bills and taxes didn’t end up in him going to jail (Hill had to spend three months behind bars). Still, the rapper did suffer some harsh consequences after the unpaid bills kept on accumulating as the years passed.
It seems Tyga loves to rent luxurious properties very often, but he's not a fan of paying for those expensive leases. Eventually his sports cars, watches, and houses were repossessed form him... at the end of the day he's still a rap star though, so he's probably far from worrying.
#1. Nicolas Cage
Nicolas Cage has earned millions of dollars from the extensive list of successful movies in which he has worked in, including Moonstruck, Face/Off, and Lord of War. Though some of his projects flopped, one can't help but respect his work ethic:
In 2018 alone, he was involved in 8 movies. Impressive, right? However, like his Hollywood colleague johnny Depp, Nicolas has a knack of spending millions on extravagant things, like a private jet or an island in the Caribbean. When a multimillionaire divorce hit him, and the IRS made him pay almost 15 million for tax evasion, Cage was forced to tighten his belt for a while!