15 Celebs With Riches To Rags Stories

August 2024 · 11 minute read

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Everybody has a story. Whether they're as rich as the president or as poor as the homeless, people have their strengths and sorrows. Both sides of the coin have a shine.

The cheesy metaphor means that people are just people. They all breathe air, use toilet paper, and pee in the shower. Unlike Kim Kardashian or Donald Trump, average civilians keep to themselves. They're unaccustomed to a million likes on Instagram or 30,000 re-Tweets on Twitter.

If they want their fame, they have to “work, work, work, work, work (Rihanna reference).” After they've invested their sweat, blood, and tears, they have to wait for their break. Only the lucky ones have a chance to build their fandom, raise their platform, and speak their peace. However, if they're lucky enough, they can tell their stories, and their rags-to-riches reveries will be acknowledged as inspirations to aspirants everywhere.

However, what if the tables were turned? What if the artists had the talent and luck, but without the struggle? Their come-up may have a weaker impact on the masses, but the creatives still face hardship, regardless. Think about all of the stars who were at the height of their success; then think about how they hit rock bottom months or years later.

You can feel the sting from here, and you feel sympathy for triumphant men and women now defeated. Nobody wants to see their beloved idols in pain. While rags-to-riches stories should be rightfully celebrated, the riches-to-rags stories should be rightfully mourned.

O.J. Simpson

O.J. Simpson has become a household name with the help of American Crime Story and Robert Kardashian. His infamous trial for the murder of his wife peaked the interest of 150 million people. They were unable to fathom how an all-American football hero was now an alleged murderer.

Simpson was acquitted of the crime, but he lost everything and everybody in the process. He was left spiraling deeper and deeper down the rabbit hole. “He was arrested in 2007 during a botched robbery in Las Vegas. He was charged with a number of felony counts, including kidnapping and armed robbery. He was found guilty and sentenced to 33 years in prison. Simpson will be eligible for parole in October 2017,” an ABC News article states.

Todd Herzog

Todd Herzog was Survivor: China's winner, and his victory gave him a pricey $1 million. He was supposed to feel like a king, but he was living more like a peasant. He had a huge problem with alcohol, so he went on Phil McGraw's show Dr. Phil, to receive treatment. He was the host's guest three different times.

2013. 2014. 2016.

The survivor had a difficult time staying sober, but he has high hopes for his future. He may be optimistic, but his mother's extremely worried for her son. “His mother also said her openly-gay son would guzzle down up to three bottles of vodka a day, and she feared every day he might die,” a tabloid magazine claims.

Amanda Bynes

Amanda Bynes was growing her wealth with her comical shows like The Amanda Show in the early 2000's. She was successful at a very young age, but she also faced temptations at a young age, too. She was surrounded by leeches, users, and abusers. She eventually gave in to the influences around her. By 2014, the actress had lost everything. “A report claims Amanda has no access to her millions, and she's homeless. ‘Amanda doesn't have access to her $5.7 million, and is only receiving money through $50 and $100 gift cards given to her by her parents,’” according to the gossip.

She had seen better days. However, she was going through a difficult time. She seemed to be doing much better in 2016. “Amanda is doing great, enjoying school and thriving,” her lawyer stated.

Drake Bell

Drake Bell was mainly known as the hot rebel from Nickelodeon's Drake & Josh, but the guitarist had fallen from his pedestal. In 2011, the actor was involved in a lawsuit with the producer of A Reminder. He dealt with more than lawyer fees and a courtroom. He was embroiled in a contention with Justin Bieber, and became bankrupt to boot.

Bell had his issues. He made snide remarks towards Bieber, grappled with the foreclosure of his mansion, and survived a horrific car crash, but he was still undefeated. He kept trying.

Watch him continue to try on his YouTube channel.

Bobby Brown

Bobby Brown will always be known as Whitney Houston's ex. Always. However, he has a life outside of the deceased icon.

Does he really, though?

According to the R&B crooner, he cared for Houston in her time of need. “Brown is claiming that he financially supported ex-wife Whitney Houston and daughter Bobbi Kristina's lavish life-style, while the late singer underwent drug addiction treatment at a rehab facility,” stated an article. The millionaire asserted how he was such a benefactor by giving his former wife $10,000. He wanted her and their daughter to be comfortable in an expensive hotel.

While the article was posted five years ago, Brown's name is only associated with the “I Will Always Love You” singer's name. Whether he's talking about her purported bis*xuality or writing a tell-all about her, Brown will do whatever and whenever to make money.

Is he a hard worker, or is he just another user?

Tyga

Tyga has been a critical part of Young Money Entertainment, a group mainly comprised of Lil Wayne, Drake, and Nicki Minaj. He's past the flashing lights and fancy cars, though. He's now a father to his son with Blac Chyna, and he's also the boyfriend of Kylie Jenner, the younger version of Kim Kardashian. He may be attached to wealth through his connections, but is he wealthy himself?

He had financial problems with his landlords, and his foreign car was repossessed. “The ‘Rack City’ rapper had to give his landlord $186,000, but Tyga was also involved in an eviction case with another landlord. Tyga failed to pay rent and other amounts due,” an article stated.

Even though he owed thousands upon thousands of dollars to various people, he was still buying expensive items. When Jenner turned 19 years old, he bought her several pricey gifts. Jenner may have been ecstatic about her brand new Mercedes, but she'd be very disappointed if she had to foot the bill. Instead of buying a vehicle, Tyga should've bought fiscal counsel. The investment would make more sense.

Ray J

Ray J and Kim K made a s*x tape that went viral, and the stars basked in the fame and fortune of their saucy collaboration. However, they reached different rungs of success. Kardashian was involved in lucrative television shows, book deals, and marriages. Her male counterpart made millions, too. He just made less money than her.

Kardashian's current husband, Kanye West, shared the same sentiment. He said that white girls usually date prominent, black men. According to West, his wife “has dated broke, black dudes,” too. Kardashian's dated plenty of men, but West's jab was probably directed at Ray J, a man who's name's synonymous with the doyenne.

Ray J's still blessed, though. He has more money than most of the American population. He just has a minimal amount of money compared to the Kardashian, Jenner, and West dynasties; c'est la vie.

Lamar Odom

Lamar Odom may no longer be married to Khloé Kardashian, but he's still making money. He's at least making money in 2016 onward. However, he almost died a year prior to his recovery. In October of 2015, the basketball star was found comatose in a Nevada brothel. When medics arrived on the scene, he was unresponsive. “Odom was reportedly found to have ‘virtually every drug imaginable’ in his system, including crack cocaine, and may have suffered a stroke. He is on life support and fighting for his life,” an article reads.

He and Kardashian split because of his addictions. While she prospered in her personal and professional endeavors, Odom was diving deeper and deeper into the hole of drug addiction.

He's sober now, but will he be able to maintain his recovery?

Josh Duggar

Josh Duggar rose to fame with his parents' reality series 19 Kids and Counting. The show documented the Christian with more than just his family, though. He was in a budding relationship with his then fiancée, and their love was exploited on national television.

They seemed like a cute couple, but the aired episodes portrayed the fantasy, and not the reality. Their reality was more twisted than anyone could ever imagine. Anna was married to a cheater and molester. What was worse? Anna knew about the molestation before the world knew, and she still stood by his side.

The couple and their children lost everything. Duggar left his comfy position at the Family Research Council, moved out of his sprawling home, and drove back to Arkansas. He now serves as a used-car salesman to provide for his pregnant wife and four children.

Lindsay Lohan

Lindsay Lohan was one of the most coveted actresses in Hollywood. Then she began using drugs and alcohol. Her days of lighthearted comedies like Mean Girls and Freaky Friday were quickly put to bed. The party animal within Lohan was suddenly unleashed. “Lohan's coke habit cost her anywhere from $3500-$5000 a month,” an insider relayed.

According to the source, the golden girl of Hollywood had expensive taste. Let's hope she could make her rise back to the top sooner rather than later.

Doug Hutchison

Doug Hutchison used to be known for his role in The Green Mile. However, he's more known for his marriage to blonde bombshell Courtney Stodden. The couple was an odd pair. Hutchison was in his early fifties when they wed while Stodden was just 16 years old at the time.

They were bound to have a problem or two, and their fame only escalated and exploited their underlying issues. There was a reason why their reality show never began, and thank goodness for the small favor. Stodden was just a teenager, and Hutchison was in a reverie of delusion. They needed therapy, and they needed a few more years between them.

While their union propelled Stodden into the limelight, the publicity hindered Hutchison's career. “Doug's agent and manager dropped him, his brother has cut ties, and his mother wants nothing to do with them,” an ABC News article stated. Ouch!

Lil' Kim

Lil' Kim will always be respected as one of the rapping world's finest female artists. Her music has done more than just revolutionize the industry. Her lyrics have inspired individuals across the globe.

Has anybody ever heard of Nicki Minaj?

However, no amount of adoration can save Lil' Kim from her own decline. While the “How Many Licks” rapper has her millions, she's experienced a period of stagnation, not to mention financial turmoil. “Lil' Kim owes $126,725.12 to the Federal Reserve. This is not the first time that Kim has failed to pay the taxes,” an article relays.

She was sent to prison, and her stint only worsened her financial crisis. According to the article, the mother's been in debt since 2002. She's a mom to toddler Royal Reign now, so the rapper has even more bills to pay. Will she be able to handle the fiscal stress?

Spencer Pratt

Spencer Pratt was a protagonist on MTV's The Hills, and he met his wife Heidi Montag through the show. They were living an extravagant lifestyle because of their paychecks, but the two were diving deep into debt. Pratt would spend his money on pricey meals, designer clothing, and crystals. “After years of overspending on frivolous things like $3,000 bottles of wine, $15,000 Hermes purses, and $10,000 crystals, Spencer Pratt and his wife have whittled away their fortune, which must have been over $10 million,” a gossip magazine stated.

He was wasting money, so he could live like a movie star. However, he soon learned his lesson. He had to prioritize what was important and who was important. He and Montag are expecting their first child in 2017, after all.

Courtney Love

Courtney Love's still a millionaire, and she's still the owner of hundreds of millions of dollars. She's only broke by Trump's standards.

However, she has lost millions of dollars, too. She even admits to her past of financial woes. “‘I lost about $27 million,’ Love said, explaining that much of the dough went towards settling several lawsuits over the years,” an article relays.

She was undeterred by her losses, though. She pushed through her pain in other ways. “I had to run very fast to look after my money and I felt cocaine helped me do that. So I started taking cocaine and that turned into nine months of crack,” Love revealed.

Some people rely on coffee, and other people rely on cigarettes. Love just relies on her daily dose of cocaine in the morning. Everyone has to summon their energy, somehow.

Toni Braxton

Toni Braxton may be a prominent R&B lyricist, but she's just like everybody else—in debt. The woman owed millions and millions of dollars, and she claimed bankruptcy in 1998. She was flippant with her finances, but her bank account seems to be in a stable place now. “The 45-year-old agreed to pay $150,000 to settle the case. She had run up debts between $10 million and $50 million,” an article states.

She was in such a financial pit that she auctioned the copyrights to a few of her own songs, but she had to find a way to pay her debt. However, she seemed to finalize a deal with the help of a judge, so she could find relief from her financial burdens. She monitors her budget now, but her mistakes will always serve as important reminders.

Like the other fourteen celebrities, Braxton proves that more money can always mean more problems.

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