Not too long ago 50 Cent was one of the richest rappers in the hip hop industry, second only to billionaire, Jay-Z.
At the height of his wealth, Curtis "50 Cent" Jackson was said to be worth $155 million after tax, according to Forbes' annual Hip Hop's Wealthiest Artists list. He'd been on the same list every year since its inception in 2007.
But a flailing music career, several legal battles and poor business investments plummeted his net worth by a whopping $200 million, forcing him into bankruptcy with a debt of $32.5 million.
For someone who was the pin-up hip hop star of the 2000s, with hits like Candy Shop and In da Club, and who also built an impressive investment portfolio worth tens of millions, the story of how "fif" fell from grace is astonishing.
Columbia Records signed 50 Cent, now 43, in 2000, before canning his first album Power of the Dollar after he was involved in a shooting.
50 was attacked by a gunman in May 2000 outside his grandmother's former home in South Jamaica, in broad daylight at 11.20am.
The attacker walked up and fired nine shots at close range with a handgun. 50 was shot in the hand, arm, hip, both legs, chest and left cheek, while his son was inside the home and his grandmother was only metres away in the frontyard.
His facial wound resulted in a swollen tongue, the loss of a wisdom tooth and a slurred voice.
He spent 13 days in hospital, while the alleged attacker, Darryl Baum, Mike Tyson's close friend and bodyguard, was killed three weeks later.
50 Cent had been dealing drugs since he was 12 years old in the volatile area.
In his autobiography, From Pieces to Weight: Once upon a Time in Southside Queens, he wrote: "After I got shot nine times at close range and didn't die, I started to think that I must have a purpose in life … How much more damage could that shell have done? Give me an inch in this direction or that one, and I'm gone".
50 made a full recovery after five months. When he left the hospital he stayed with his girlfriend, Shaniqua Tompkins, and their young son, Marquise Jackson.
Using the near-death experience as a means to turn his life around, 50 Cent began recording again when he was discovered by famous rapper Eminem, who signed him to Shady Records.
This is where he produced the album that would make him a bona fide star, Get Rich or Die Tryin'.
The album, released in 2003, debuted at number one on the Billboard 200, selling 872,000 copies in its first four days.
Over the course of his career he has sold over 30 million albums globally and has also picked up a sweep of awards, including a coveted Grammy Award, 13 Billboard Music Awards, six World Music Awards and three American Music Awards.
He also threw his hat at Hollywood, appearing in several films including the semi-autobiographical film Get Rich or Die Tryin', Home of the Brave and Righteous Kill.
While his music career has been stable ever since he started out, he never quite reached the same heights of his debut album. Luckily the rapper branched out as soon as his career took off and tried his luck in business, making most of his millions through investing in companies, stocks and bonds.
His business and investment portfolio has spanned across a broad sector of real estate, financial market investments, mining, boxing promotion, vodka, fragrances, consumer electronics and fashion.
He signed a five-year deal with Reebok in late 2003 to distribute a G-Unit Sneakers line for his G-Unit Clothing Company, named after his hip hop group which was formed in 2002.
One of his first ventures — and ultimately his most successful — was in 2004 with Glacéau VitaminWater, for which he created an enhanced water drink called Formula 50. He was given a share in the company to sign on as a spokesman for the brand, which he promoted in songs and interviews.
In 2007, Coca-Cola purchased Glacéau for a whopping $4.1 billion and, according to Forbes, 50 earned $100 million from the deal after taxes.
It was only the beginning of his lucrative business opportunities.
50 joined Right Guard to introduce a body spray (Pure 50 RGX), he endorsed Magic Stick condoms and signed a multi-year deal with Steiner Sports to sell his memorabilia.
He also founded two film production companies, G-Unit Films and Cheetah Vision.
In 2014, 50 became a minority shareholder in Effen Vodka, which is made in the Netherlands, after investing an undisclosed amount in the company Sire Spirits LLC.
Later that year he signed a giant $78 million deal with FRIGO Revolution Wear, a luxury underwear brand, which retails its underwear at about $US100.
"50 Cent made around $300 million in two years," Zack O'Malley Greenburg, Forbes senior editor, told The Post.
"He has always been really good at profiting off whatever his situation is. He even marketed getting shot nine times."
But in July 2015, in an announcement that shocked fans, 50 Cent declared bankruptcy with a debt of $US32.5 million. According to TMZ, he struck a deal to pay $23 million in debts over five years.
The filing came several days after a court ordered him to pay $7 million to Lastonia Leviston whose sex tape he posted online without her consent. The reason he did it was reportedly because she dated his long-time enemy, Rick Ross.
The previous year, 50 was ordered to pay $17 million to headphone manufacturer Sleek Audio, after a failed deal to launch his own headphone line.
50 partnered with Sleek Audio in 2011 for his own Sleek by 50 line, but after it fell through the rapper filed suit over allegations the company did not refund him his initial $2 million investment.
He then switched camps and launched an earphones line with rival company SMS Audio, which Sleek Audio executives claimed he ripped off.
Even after losing millions in several lawsuits and his music career no longer hugely profitable, there were still many questions about how 50 managed to fritter away more than $150 million. Finance experts predict it came down to several of his investments and businesses going bad and reckless spending, including renovations on his 18-bedroom mansion in Connecticut and a string of luxury cars.
A portion of his investments also lost value during the 2008 recession.
In addition, his movie production company G-Unit was shut down. His second movie company, Cheetah Vision, has not proved a huge financial success.
50's once hugely popular clothing company, G-Unit Clothing, severed ties with its parent company, Marc Ecko Enterprises, in 2008 and hasn't seen the same success since.
His boxing promotions company also went bust.
Documents from US Bankruptcy Court in 2015 revealed 50 was making $185,000 a month from existing marketing and promotional deals, but was spending $72,000 on his home — in addition to $108,000 in other expenses.
Remarkably, 50 emerged from bankruptcy earlier than expected in February 2017, after reportedly paying off all his debt.
His lawyers said he paid off the five-year plan early with $8.7 million of his own money and $13.65 million he received in a settlement of a legal malpractice lawsuit against his other lawyers.
He also just sold his mansion for $US2.9 million. A spokeswoman for 50 Cent told the Wall Street Journal proceeds of the sale were going to be donated to the rapper's not for profit charity, the G-Unity Foundation, which improves quality of life for low income earners across the US.
Despite being debt free and performing shows here and there, as well as maintaining several investments, it seems 50 is still in need of cash.
Only last week, he issued a bizarre warning on Instagram, seemingly directed at people that owe him money.
He posted a clip of a dead man with the caption: "Yeah what he said, but no mouth to mouth PUNK. if you die your debt moving to ya next of kin."
He regularly rants about being owed money on social media.
As of 2019, Celebrity Net Worth estimates 50 Cent's net worth at $US30 million.