When admiring the manly manliness of Will Smith and his fiery success of a career, it’s hard to fathom that he was ever anything but a multi-talented king, standing upon a mountain, stacked high by countless movie awards, music awards, and roughly $250 million breeding in his bank account. But truthfully, things were not always so abundantly prosperous in Big Willy’s life. In 1987, Mr. Smith was blinded by his Grammy award-winning hip-hop duo, DJ Jazzy Jeff & The Fresh Prince, and he spent his money without any restraint, laughing as he ignored the red letters from the IRS. Bad move, William, as the government eventually caught up as always, and informed the star that he owed them $2.8 million. Smith lost everything including his house, and he was living minutes away from full bankruptcy. That was until 1990, when the angels of finance smiled upon him and granted the rapper a second chance, with a television show called The Fresh Prince of Bel-Air. This sitcom was an unstoppable success and Will Smith has been sickeningly rich ever since. Looks like someone learned their lesson.

Sadly, this story is only one example of a greater Hollywood trend, one where superstars spend all of their money because they think they’re actually gifted and not just lucky. So come with us now on a journey through celebrity accounts, as we witness our heroes spending more money than we’ll ever know, and then ending up more broke than we’ve ever been.

Lady Gaga

In 2009, Lady Gaga had just begun to sink her claws into the world and peel its skin back. Her debut album (The Fame) had come out the year previous, quickly shooting her to the uppermost layer of the cake, selling 15 million copies worldwide, hitting the top of the charts around the globe, and going on to be nominated for five Grammy Awards. When Gaga looked at her bank slip, she noticed that there was suddenly $3 million in there, and so she spent it all immediately on her 2009 Monsters Ball tour, gone. It’s funny to think that while Stefani Joanne Angelina Germanotta was commanding those massive crowds on arena stages with fourth top-ten singles to her name, she was completely bankrupt that whole time. Luckily, the gamble paid off, and once the tour came to an end, a brand new check worth $40 million was delivered into her hands. She’s a smart one, that Gaga.

Mike Tyson

The bigger they are, the harder they fall, and Tyson was pretty big. After the man had punched his way to the top of the boxing heavyweight championships, life began to fight back, sending him directly to jail for three years and leaving him with $23 million in debt around 2003. This forced him into a chokehold where he had to declare bankruptcy, which is impressive considering that Mike had earned over $300 million over the course of his career. Where did the money go, dude? No one knows for certain, but there are theories, such as his divorce settlement, his legal fees, money owed to the IRS, his car addiction, his cocaine addiction, or even how much it cost to keep his pet tigers happy. All’s well that ends well though, and his net worth has recently settled up to around $3 million, which I’m sure Tyson is desperately hanging on to with both of his scary arms.

Larry King

With a promising radio career over the course of the 1960s, King’s professional life wobbled then crumbled in 1971 after he was fired from every single one of his jobs at the exact same time. How did this happen? It turns out that his employers were a little concerned when Larry was arrested for allegedly stealing $5,000 from his former business partner. These charges were eventually dropped, but the black mark of shame smeared across King’s face was not so easily erased, and he spent the next few years walking aimlessly around Miami with an empty tin, begging for people to listen to him announce the sports news, even though maybe he didn’t do that, I made it up. Regardless, in 1978, Larry was around $352,000 in debt, filing for bankruptcy just before he was offered his own radio show that same year. This evolved into his exceptionally successful television program Larry King Live which ran for 25 years. He's no longer bankrupt.

50 Cent

Back in 2007, 50 Cent was known as the second wealthiest rapper in the game behind only Jay-Z, which is surprising when considering that 50 Cent sucks. Regardless, his ventures into the fashion world, book publishing, performance-enhancing waters, film productions, boxing promotions, and even mining metals, all managed to keep his revenue line above the reported $155 million mark. That was until 2015, the year everything went wrong, when (real name) Curtis James Jackson III was sued for posting an adult tape of Rick Ross’ ex-girlfriend Lastonia Leviston online ($5 million), and for stealing headphone designs which he used in his own Sleek by 50 product ($17.2 million). Not long afterward, it suddenly became public knowledge that 50 didn’t quite have the cash he’d been rapping about, and he filed for bankruptcy later that year.

Gary Coleman

What'chu talkin' 'bout, Willis? Well, roughly $72,000 in debt, Mr. Coleman. Gary’s fame seed came from the American sitcom called Diff'rent Strokes which ran from 1978 to 1985, and there was no doubt that this 17-year-old was the loveable central star of the whole show. At the height of popularity, Coleman was going home with a wad the size of $100,000 per episode in his pocket, but this was not enough, as the fingers of his parents, advisers, lawyers, and the taxman all picked him dry. By the time the series had ended, Coleman was left with basically nothing and did what any Hollywood child star would do in his position: he sued his parents. He won the case, $1.3 million came back into his hands and then he spent it all. This story only gets worse from here, close your eyes: Gary filed for bankruptcy in 1999, attempted to kill himself twice, and then actually died from an epidural hematoma in 2010, at age 42.

Meat Loaf

There are reasons to be jealous of Meat Loaf, and reasons not to be. With worldwide record sales exceeding 80 million, he is one of the best-selling music artists ever, inventing the operatic rock genre and starring in some of the greatest films of the last century (including The Rocky Horror Picture Show, Fight Club, and Spice World). On the other hand, he’s had 18 concussions, crashed his car, crashed his plane, broke both his legs falling off stage once, collapsed on stage unconscious twice, and has had a heart attack, so my life looks pretty good from here. But at least he’s super rich, right? Actually, no. Despite 1997’s Bat Out Of Hell selling 43 million copies, Meat Loaf had signed a dodgy contract and never received a penny from that. "It’s still humiliating," Loaf confessed. "I declared bankruptcy and everybody said, ‘Oh, he’s spent all his money,’ but that wasn’t the case. I made almost nothing."

MC Hammer

MC Hammer's name is now synonymous with those times that fame lifts you up and then drops you back down from an elevated platform. In the 90s, Stanley Kirk Burrell was famous for like 20 seconds, and in that time, he managed to release some hugely successful singles, such as U Can't Touch This and 2 Legit 2 Quit, now considered pop-rap classics which lead the scene to glory whilst wearing the baggiest pants the world had ever laughed at. And with $33 million to his name, what did MC have to lose? He had $33 million to lose. After living the flashy superstar lifestyle with a steady income, the money dried up when the album sales dropped, and Mr. Hammer was left with $13 million in debt. He applied for bankruptcy in 1996, his mansion was sold for a slice of its original price, and MC became a Christian preacher shortly afterward, begging God to help him.

Aaron Carter

Aaron is famous for being one-fifth of the best-selling boy band in history (130 million records worldwide), a team who have stuck together through thick and thin, continuing to remain strong since 1993 until this very day. I’m talking, of course, about the incredible Backstreet Boys. Wait, what do you mean Aaron wasn’t in the Backstreet Boys? Oh, that was his brother? Whoops, too late to un-type that now. Aaron did ok himself though, right? He sold a million copies of his debut album at age 10 thanks to his famous bro, and then he quickly fell down for the rest of his life, getting arrested for marijuana possession in 2008, then filing for bankruptcy in 2013 due to his $3.5 million debt hole. Recently, Carter seems to have got back on his feet, clearing his money issues in 2014, coming out as bisexual in 2017, and even releasing another terrible album earlier this year.

Toni Braxton

Un-Break My Heart? More like, Un-Break My Bank Balance hahahaha! Wait, even more like I'm Toni Braxton and I'm Broke hahahaaaa! The rest of this story is not funny at all. Despite 20 million records sold by 1996, Braxton had seen no money and retaliated by blasting a lawsuit against her labels, Arista and LaFace Records. These multimillionaire companies had more expensive lawyers, the lawsuit was unsuccessful, and that little undertaking pushed her deeper into the debt quicksand, straight into bankruptcy. The girl eventually got back on her feet, but in 2010 she was diagnosed with a heart disease, meaning she couldn't play an agreed Las Vegas show. Everyone sued everyone until Braxton was back in the bankrupt box for the second time. She has since completed some required financial courses, and most of her debt was written off in 2013.

Marvin Gaye

Once upon a time, the Prince of Soul and Motown was earning $100,000 a night, which in the mid-70s, was a lot of money, much more than it is now. Actually, even now, that's a lot of money! Anyway, due to a severe addiction to cocaine, $4.5 million owed to the IRS, and his first wife Anna suing him for child support, this money simply wasn't going to cut it. But Gaye had a plan! He filed for bankruptcy, agreed Anna could have all the profits from his next release, and then recorded a purposefully uncommercial album just to ensure Anna didn’t get any cash whatsoever. Marvin then ran away to Europe, hiding from his taxes, continuously taking more drugs until he lost his mind, moving back in with parents, and then finally getting fatally shot dead by his own father. What a legend!

Burt Reynolds

With many box office smash performances and one Academy Award nomination to verify his skills, Burt Reynolds is proof that talent and a heightened perception about mustache hygiene does not automatically transfer into financial know-how. His first error was the most obvious one: he was living a glamorous lifestyle paved with $100 bill notes, certain that the money tree in his pockets would only continue to grow because that’s how money trees work. And, in all fairness, this might have been ok, if it weren’t for his second error: where he invested in a Florida restaurant chain which completely failed because Burt Reynolds is an actor, and these were real restaurants. But it took one more error to truly sink the man: actress Loni Anderson, who divorced Reynolds and took the final shreds of his wallet until Burt filed for bankruptcy in 1996. But don’t worry, two years later, and Burt had sorted it all out, still making films, still has a mustache.

Kim Basinger

In 1993, a mystery thriller film called Boxing Helena came out, and when you delve deeper into the movie’s history, it’s quite impressive that it was even made whatsoever. The plotline was about an obsessed surgeon who kidnaps and amputates pieces off of his crush, which is weird, but surprisingly not this movie's biggest problem. The main snagging point came when the production company could not hold down a lead actress willing to get cut up, with Madonna jumping ship before filming began, and then second choice Basinger disagreeing with revisions and leaving herself. The studio had lost so much money at this point that they attacked Kim in court, suing her for $8.1 million, and then winning the case. This forced Basinger into bankruptcy, but she successfully appealed, and the amount was dropped to $3.8 million. This was enough to get the film finished with actress Sherilyn Fenn instead, and the critics loathed it.

Sinbad

Hahaha, remember Sinbad? No? I almost do! I remember he was on my TV once back in the 90s. I was really young in those days but even at that undeveloped age, I knew he wasn’t funny. Which is why this story surprises me more than the others on this list, because when I read that Sinbad once owed the state of California $2.5 million in income tax, I couldn’t believe he’d ever seen money like that in the first place. From doing what? Has he ever made a good joke whatsoever? Either way, at least his bank account was funny, because, in 2009, Sinbad had to confess that he hadn’t earned any money for over a decade, and filed for bankruptcy, eventually selling his 2.5-acre home just to get out of trouble. Despite everything I said, I do hope he’s ok though because I'm trying to be a nicer person.

Mark Twain

Famous for his intellectual charm and written wit, Mark Twain’s crowning achievements came in novel form, namely The Adventures of Tom Sawyer and it’s sequel Adventures of Huckleberry Finn, both of which are considered staples of great American literature to this very day. Due to his recognized talent, Twain was a wealthy man and decided to invest about $300,000 of his riches ($8,000,000 now) in a brand new typesetting machine. This bit of equipment was predicted to revolutionize the printed word, but what it actually did, was break down all the time until no one wanted it anymore. Mark lost everything. He filed for bankruptcy, then worked furiously hard on his lectures until he had just about regained his once financial glory. But if the history books are anything to by, Twain was never the same again, his friends stating that the man had lost his revered sense of humor completely, ultimately dying an unfunny person.

Isaac Hayes

In 1972, Isaac Hayes was living every musician's dream, winning not only two Grammy Awards, but also a Golden Globe and an Academy Award due to his acclaimed score for the film Shaft. And then suddenly, everyone lost interest, and despite the man continuing to release critically acclaimed work, no one was buying it. Four years later, Hayes was forced to admit defeat with $6 million in debt, filing for bankruptcy, losing his home and all of his music rights. But then, in 1997, his vocal cords found a whole new generation of ears to soothe, as he was hired to be the voice of Chef in South Park, making money once more! Sadly, Hayes quit the show in 2006 due to a disagreement over the portrayal of his Scientology religion, and the man rapidly spiraled down after that, passing away in 2008. Sorry to end on such a downer, but usually people don’t read this far anyway.