15 Celebrities Who Lost it All

It’s everyone’s dream to have a multi-million dollar fortune with which to support themselves, their families, and all their lavish whims. Having enough money to purchase a few islands (and then some) sounds like a bottomless pot of gold. Surprisingly, the illusion can slip away just as easily as the money itself — quickly, and with devastating effects.

Lenny Bruce

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Lenny Bruce is considered one of the greatest comedians of all time as well as one of stand-up’s legendary pioneers. His act was always shocking, sometimes crude, but never dull. Here’s a clip from the 1974 biopic, Lenny, starring Dustin Hoffman. It’s a verbatim performance of some of Bruce’s comedy, and a clear example of exactly what rendered him so controversial. Because he dealt with taboo subjects, Bruce was almost always being hounded with obscenity charges, and, under pressure from the police and was blackballed from almost all the comedy venues in his native New York.  

His career reached breaking point in 1961 when he was put on trial for yelling the f-word while pummeling a Catholic nun with a puppy he lit on fire. Just kidding — he actually said the word ‘cocksucker’ at one of his comedy shows, in the presence of grown men and women who were appalled and supported the lawsuit instead of simply leaving the club. All the legal costs of the trial cause Bruce to fall into bankruptcy and he died a short five years later from an accidental morphine overdose in his bathroom. Flash forward to 2003, thirty-seven years later, when New York Governor George Pataki granted Lenny Bruce the first posthumous pardon in New York state history.  Dick Schaap summed it up best when he wrote: ‘One last four-letter word for Lenny: Dead. At forty. That’s obscene.’ 

Dustin Diamond

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Dustin Diamond is best remembered as Screech from the classic 90s TV show, Saved by the Bell, though that’s taking a pretty loose definition of the word ‘remembered.’ His character basically existed to make everyone feel better about themselves, all while taking on vocal characteristics so ear-burstingly painful that they ruined this scene from Dumb and Dumber.  

Very unsurprisingly, Dustin found it hard to find work after Saved by the Bell wrapped. He turned to stints on reality TV shows such as Celebrity Fit Club, where he lived up to his former character and couldn’t shut his mouth, leading to a near ass-kicking. Recently, Diamond’s home has gone into foreclosure and he’s resorted to selling t-shirts emblazoned with ‘I paid 15 dollars to help Screeech save his house.’ Seriously. Oh, and that’s not a typo – he wasn’t allowed to use the character’s name based on copyright. Perhaps Dustin’s most famous exploit since his fall from teen (semi)stardom was his brief foray into the world of porn. Diamond appeared with two women in a debaucherous video that culminated in the eternally classy dirty sanchez. Diamond claimed that he didn’t intentionally leak the video, yet his manager sees it as a positive thing that may help him escape being typecast. Oh boy.

MC Hammer

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The music. The dancing. The pants. MC Hammer was a revolutionary hip-hop artist who truly changed the genre’s landscape by helping to bring it into the mainstream. Hammer (born Stanley Kirk Burrell) is best remembered by literally everyone for his perennial hit ‘U Can’t Touch This.’ Even his mom is sometimes a bit hazy regarding his identity until his does that crab-walk thing. Don’t pretend you’ve never tried it.  

Due to brash spending (living in a $30 million mansion and having a monthly payroll of $500,000), dwindling album sales, and overspending to support and embellish the lives of members of his family, the rap superstar’s funds went quickly down the drain. Hammer was forced to file for chapter eleven in 1996, permanently ending rumors that the majority of his fortune was kept in his pants.  

Nicholas Cage

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Nicolas Cage makes for a surprising bum — he’s still famous and making (really awful) movies, besides his latest role in kick-ass, reminding audiences of his early humorous turns in films like Raising Arizona.

Apparently, Cage owes $6.2 million in back taxes, which is the second scariest thing he’s ever faced. Because of ‘improperly deducted personal expenses,’ Cage is being forced to sell both his $3.5 million mansion in New Orleans and his $35 million house in Hollywood. He has only paid the IRS $666,000 so far — possibly in some cryptic attempt to compare them to Satan — but he still has a long way to go.

Mike Tyson

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Mike Tyson was once a very rich man. In the course of his boxing career, Mike Tyson earned a reported $300 million. Yet, in 2003, he filed for bankruptcy, citing his lavish $400,000-a-month lifestyle as the probable cause. Either that or his $9 million divorce from his (second) wife. What makes Tyson’s bankruptcy even more remarkable is that several of the fights leading up to his decent into the red carried payouts of over $30 million. Basically, it comes down to this: Mike Tyson is pretty much batshit insane. At least he’s appearing in films with a little more substance than anyone else on this list so far.  

Pamela Anderson

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Pamela Anderson’s fame can be allotted mostly to her vibrant, yet subtle, acting. After making a name for herself by appearing in Playboy and sending men-of-taste everywhere into a frenzy, she gained her initial television fame on the show Home Improvement. Anderson’s star status was certainly sealed by her turn as C.J. Parker on the classic Baywatch, a role that suited her down to a tee. Not only did she look good in a swimsuit, it was absolutely impossible for her to sink, thus making rescue scenes a cinch to film. Staying afloat in the literal sense has always been much easier than in the financial interpretation for poor Pam. She’s currently living in a trailer while her Malibu beach house is under construction, but is plagued with fears that it is going so far over budget that she may never get a chance to live in the home at all. Pam is obviously confused as to how the budget blew up to $3 million over the estimate so quickly. Here’s a hint, Pammy: it might be the platinum-plated swimming pool you decided on. 

Lindsay Lohan

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Lindsay Lohan was once just a freckly young girl with a fairly decent attempt at an English accent. These days, she’s still freckly, but a lot more wild, with tales of drug addiction, recklessness, and general excess surrounding her at all times. The last few years have been particularly tough for the young starlet, with DUI charges, public feuds between herself and her father, and more and more negative attention from the media. Rumors of Lohan’s financial troubles have been circulating for over two years, and the laundry list of lavish spending she’s accrued certainly seems to make the rumors plausible. Lohan apparently spent $7 million in the space of only three years and was forced to sell her apartments in both Los Angeles and New York. This spending was compounded by time spent in rehab, legal fees, staying in a $1200-a-night hotel room for an entire year, and generally blowing money on things that girls like to buy (only multiplied by ten thousand).  

Danny Bonaduce

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The only person to outdo Dustin Diamond’s level of pathetic-ness is the lunatic Danny Bonaduce. Of the same ilk as screech, Bonaduce is a former child actor bent on completely destroying his public image and changing the way everybody views The Partridge Family. Bonaduce might legitimately be insane. He has sucker-punched a transvestite in the face, leading to probation and the loss of his job at KKFR radio. Bonaduce has thrown a reality TV star into the air to make his victim smash his face on a stage during a live awards ceremony, and he’s had an on-air fight with Denis Rodman after insulting the former basketball star for his unconventional look. To be honest, these strange squabbles really only scrape the surface. A failed reality television show about his life in which he stalked now-ex wife in fits of jealous rage over her being in the mere presence of other males, multiple trips to rehab, and various drug addictions are all reflections of a deeply disturbed man. Bonaduce has got into so much trouble that there’s really no room to make jokes about it; it’s more shocking to just tell the truth. Bonaduce’s financial struggles have seen him appearing on z-list reality TV shows to make ends meet, but really, he is bankrupt on a far deeper level. 

OJ Simpson

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OJ Simpson is most famous for getting away with the murder of his wife, Nicole Brown, and her friend, Ronald Goldman in 1994. Simpson was found not guilty by a jury of his peers in what would become possibly the most controversial trial of the latter part of the 20th century. Although a considerable amount of Simpson’s wealth was awarded to the families of his deceased wife and Goldman, it was rumored that he still kept a fairly lavish lifestyle because of his NFL pension, which, under law, was not allowed to be claimed in damages. If this were true, however, it only serves to heighten the extreme lack of character of OJ’s next move: to write a book entitled “If I Did It”, in which he detailed exactly how he murdered Brown and Goldman in every gruesome detail. Oh, that’s if he murdered them, of course, which he definitely didn’t. For once, justice was served: the book was pulled from publication, re-licensed by Goldman and Brown’s families, and given a much more appropriate cover.

Tara Reid

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Tara Reid first caught the public’s eye for her brief role in The Big Lebowski, in which she offers to give the Dude fellatio for $1000. Little did we know how close this on-screen act of desperation was to the real truth of Reid’s trashiness. These days she’s on skid row, and the last seven of her movies have gone straight to DVD — a far cry from her American Pie fame. Her lowest point is not a tough one to pin down: at P Diddy’s birthday party in 2004, where her recently-augmented boob popped out of her dress for what seemed like an eternity, while she kept on smiling vacantly until someone rushed up and put her frankenboob back where it belonged.  Since then, she’s had some horribly botched plastic surgeries which have left her breasts pock-marked and frightening. On the brighter side, she’s spoken out about self love, plastic surgery, and appeared in an issue of Playboy. The Photoshop team must have been up late on that one.

Pee Wee Herman

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Anyone who grew up in the 80s remembers Pee Wee Herman, played by Paul Reubens. He was the darling of children’s television; through some sort of irresistible annoyingness he caught the imaginations of parents and children alike. Very few people know Reubens by his real name, so intense was his dedication to the Pee Wee character. He gave all of his interviews in character (much the same as Sacha Baron Cohen does today), refusing to let anyone get to know the ‘real’ him. The man lived, breathed, and ate Pee Wee… Ew.  

His show, Pee Wee’s Playhouse was a smash hit. But in July, 1991, Reuben was caught masturbating in a porno theater and was charged with indecent exposure. The media reaction to Reuben’s arrest was huge, and it had a catastrophic effect of his career for years to come. CBS stopped airing Playhouse and he found it nearly impossible to get another acting gig until his big comeback in the film Blow. These days, Reubens is on the comeback trail, starring in films and appearing on big-name TV shows like 30 Rock. There’s even a rumor that Pee Wee himself may be making a comeback.

Burt Reynolds

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Burt Reynolds, like Reubens, was one of the biggest stars of the 1980s, and one of the world’s biggest box-office draws. He was brimming with assets: he owned several mansions, a helicopter and a luxurious ranch in Florida. Unfortunately for the Bandit, he was not as good an investor as he is an actor. After some bad investments in two different restaurant chains, Burt Reynolds declared Chapter 11 in 1996, when he had $6.6 million in assets but owed $11.2 million to creditors. There are also rumors that much of Reynolds’ fortune was blown on various animal hides, which the actor was known to lounge on sexily from time to time. These days, Reynolds has experienced a slight resurgence in his career, with roles in the remakes of The Dukes of Hazard and The Longest Yard.

Meat Loaf

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Meat Loaf, whose real name, Michael Lee Aday, is much less meaty, was once one of the most successful musicians in the world. His album, Bat Out of Hell, remains the fifth best selling album of all time with 43 million copies sold since its release in 1977. He also holds the distinction of being one of the sweatiest musicians ever. Yet, despite his amazing album sales and prodigal sweat glands, Meat Loaf fell prey to that same old beast that curses many musicians – poor management. In this case, poor management meant that his two managers, Dellentash and Sonenberg, were stealing his money and then suing him for breach of contract when he tried to seek new management. Meat Loaf is also a special entry on this list because he has filed for bankruptcy on two separate occasions: in both 1983 and 1986. Since then, he has fortunately learned his lesson and has rebounded with several national tours and screen acting in films such as Fight Club and Wayne’s World.

Mischa Barton

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The OC was a mega-hit, and most of the primary actors went on to bigger and better things. Not Mischa Barton. She decided to leave the show after its third season, thinking that she could find greener pastures elsewhere. If by greener pastures you mean starring in films that either don’t get released or go straight to DVD , then the girl did a great job. On top of her recent lack of success in her acting career, Barton is also experiencing major financial woes. First, she was arrested on a DUI charge in 2007 and released on $10,000 bail. This year, she was sued by her landlord for failing to pay the $7,000-a-month rent of her New York apartment. Barton is hitting such financial lows of late that her multiple credit cards were recently declined at a drugstore. Seriously.  

Michael Jackson

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It’s basically a waste of time to explain who Michael Jackson was. He was the King of Pop, had the most successful album of all time with of 100 million copies sold, and created a vast media empire that he controlled from a fairytale ranch with amusement park rides. The man was on top of the world, with more rhinestone gloves than even the Queen of England could muster. How appropriate, then, that one of the biggest celebrities to ever grace the earth was also subject to what could be called one of the most devastating bankruptcies on record. When he passed away, Jackson was massively in debt: he had canceled out on a number of tours and his assets had been mismanaged for years, leaving a whopping $242 million debt in his name. The never-to-be ‘This is it’ tour was the singer’s last-ditch effort to eradicate his debt and move back into the black, with the first ten London dates alone promising him earning of over £50 million. But alas, on June 25, 2009, Jackson was found unconscious in bed at his rented Los Angeles mansion and was declared dead at 2:26pm.

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