These days, however, it’s nearly impossible to imagine him succeeding. In the limp, late punchline to the grim joke that is his career, Jackson — a rapper whose preoccupation with money was obsessive even in a genre fixated on it — recently declared bankruptcy. A man whose never-released Columbia debut was to be called The Power Of The Dollar, who made a reported $100 million from his stake in Vitamin Water, and who in 2007 was the second wealthiest rapper in the industry — a man who named himself after money — was now conceding he was not financially solvent. A man who rocketed to fame shirtlessly bragging about being richer than everyone else donned a suit to meekly inform the court that he was not the pillar of wealth he was pretending to be.

His popularity transcended racial, gender, class, and generational divides. Your grandmother knew who 50 Cent was. She may even have felt comfortable enough with the rapper to refer to him as “Fiddy,” as every white person in the world once did. Backed by his mentors Dr. Dre and Eminem, Jackson once had so much power behind him that it seemed nearly impossible for him to fail.

There was a time when Curtis “50 Cent” Jackson was unavoidable. With the exception of Snoop Doggy Dogg, it’s difficult to envision a rapper getting a bigger launch: his debut album Get Rich Or Die Tryin’ dominated the pop culture landscape in 2003, selling 12 million copies while its inescapable lead single “In Da Club” stayed at the top of the charts for nine weeks. The album made Rolling Stone’s list of the top 50 albums of the decade and became one of the most commercially successful rap albums of all time.

Jackson’s struggles were once a strength: he was a hip-hop Horatio Alger story who overcame his drug-dealing adolescence and getting shot nine times to become a massive superstar. But he has only himself to blame for his downfall, and now his story has a much darker context: it’s a cautionary tale of how hubris and bad decisions can torpedo any career. Twelve years ago, the idea of 50 Cent pleading for his financial life in bankruptcy court was inconceivable. Today, his bankruptcy engenders not shock or pity but Nelson Muntz-like cackles of "Ha ha!" That's because Jackson’s fall is among the most deserved in pop culture, to the point a would-be rhetorical question like "where did it all go wrong?" has multiple, specific answers. Here are 10 of the seemingly infinite mistakes he made en route from being one of rap’s biggest winners to one of its biggest losers.

2004: Jackson uses an early Playboy interview to out himself as a homophobe

By his own account, 50 Cent’s mother was bisexual, and like many heterosexual men, he’s a lot more accepting / turned-on by the concept of women loving women than he is about men loving men. In a 2004 interview with Playboy, 50 Cent told writer Rob Tennenbaum, "I ain’t into faggots. I don’t like gay people around me, because I’m not comfortable with what their thoughts are. I’m not prejudiced. I just don’t go with gay people and kick it — we don’t have that much in common. I’d rather hang out with a straight dude. But women who like women, that’s cool. I could actually get into that, having a woman who likes women, too. We might have more in common." "It’s okay to write that I’m prejudiced. This is as honest as I could possibly be with you." 50 Cent goes on to explain, "It’s okay to write that I’m prejudiced. This is as honest as I could possibly be with you. When people become celebrities, they change the way they speak. But my conversation with you is exactly the way I would have a conversation on the street. We refer to gay people as faggots, as homos. It could be disrespectful, but that’s the facts." So don’t hate on 50 Cent: he’s just being honest about his disdain for faggots and his desire to not have them around him, and he’s from the streets, where it’s okay to call people faggots and homos. Later, the rapper revised his public take on homosexuality, but in 2010 he did tweet, "Perez Hilton calld [sic] me a douchebag so I had my homie shoot up a gay wedding. wasnt [sic] his but still made me feel better."

2005: Jackson goes without an acting coach on the set of Get Rich Or Die Tryin’

Six-time Academy Award nominee Jim Sheridan famously implored Jackson to trust his own instincts rather than professionals on the set of 2005's Get Rich Or Die Tryin'. Crowing to CHUD.com that his lead's preparation included "No art. No voice coaches, no acting coaches, no bullshit," Sheridan went on to infamously boast that he told Jackson, "You know, if this movie fails, it won't be because you can't act, it's because I didn't direct you right." By Sheridan's criteria, he did a terrible job directing Get Rich, because the film was a critical — and commercial — failure. Despite the acclaim that greeted Sheridan's previous films, Get Rich Or Die Tryin' has a 16 percent on Rotten Tomatoes. Anne Hornaday of The Washington Post captured the tone of the film's pans when she dubbed it "shockingly inert" and said that Jackson was "oddly distant and detached as a performer." A decade later, Jackson has yet to prove to anyone that he can act. He remains an eternal dilettante, always aspiring, never quite there.

2005: Jackson goes after Jadakiss and Nas (and Kelis) on the diss track "Piggy Bank"

Jackson rose to fame partially on the strength of "Wanksta," a devastating early diss track that played a huge role in ending the career of the rapper’s arch-rival Ja Rule. In the years that followed, Jackson kept beefing with everyone and everything, but it wasn’t just his new music that paled in comparison to his early stuff: his new beefs were petty and strained, and informed by increasingly knee-jerk misogyny. In the dour 2005 diss song "Piggy Bank," Jackson pointlessly went after respected New York cult rapper Jadakiss for having the gall to record a song ("New York") with Ja Rule. But elsewhere, he seemed offended simply at the idea of rappers being in love with women they treat with respect. On "Piggy Bank," the rapper taunts, "Kelis say her milkshake bring all the boys to the yard / then Nas went and tattooed the bitch on his arm / I’m way out in Cali / Niggas know you cus / First thing they say about you is you’s a sucka for love." Ever eager to prove that he was not a sucker for love, the rapper later went after Shaniqua Tompkins, the mother of his son Marquise on the 2009 diss track, "So Disrespectful," taunting, "They say first comes love, then comes marriage / Instead I got Shaniqua and a baby carriage / Then came the cash and the baby mama drama / I gave that bitch half a mil she blew it on Prada." (In 2009, Tompkins unsuccessfully sued Jackson for tens of millions in child support.)

2007: Jackson says he’ll retire from his solo career if Kanye West outsells him, then reneges

When Kanye West decided to release his third album, Graduation, the same day as 50 Cent’s Curtis, Jackson spied an opportunity to create a rivalry to pump up sales. The rapper vowed to end his solo career if Kanye sold more copies the first week out. But when West won by something like a quarter million units, Jackson surprised no one by not making good on his promise. If Kanye won the battle against 50, he slaughtered him in the war From the perspective of 2015, the rivalry, which had the unmistakable feel of an internal sales stunt (the two rappers' labels were both under the Universal Music Group umbrella), was as much a battle between wildly conflicting ideologies as it was anything else. 50 embodied a retrograde conception of the alpha-male as boorish chauvinist pig, while West personified the endlessly complicated future. As Jackson’s defeats go, this wasn’t so bad — he still managed to sell over 600,000 copies in the first week. But if West conclusively won this particular battle, he slaughtered Jackson in the war. Eight years later, West is as relevant and respected as ever, while 50 Cent is a figure and phenomenon that people think about in the past tense. Of course, that doesn't stop Jackson from continuing to take shots from the sidelines. When asked by XXL in 2012 about "Perfect Bitch", West's ode to his current wife Kim Kardashian, Jackson opined, "One man’s trash is another man’s treasure."

2008: Jackson decides that publicly humiliating Young Buck would be good for a laugh

Young Buck is a rapper so loyal that he stood trial for allegedly attacking a man with some form of cutlery while defending Dr. Dre at The Vibe Awards (the police thought it was a knife, videotape suggested it was a fork). That's the kind of man you'd want on your side, unless you're 50 Cent. In an attempt to diversify G-Unit's sound and appeal, Young Buck joined Jackson's G-Unit crew / label at the height of its popularity, but like seemingly everyone in his circle, Young Buck came to regret joining forces with Jackson. After Young Buck reportedly led a chant of "Fuck G-Unit" at a show, Jackson decided to publicly humiliate his collaborator by furtively taping a phone conversation in which Buck tearfully professed his eternal allegiance to G-Unit. The idea was to expose Young Buck as a groveler who committed the shameful sin of possessing emotions, but the stunt just made 50 Cent seem like a sociopath who turns on protégés with shocking callousness. Taking a private, dark-night-of-the-soul phone call public wasn't a boss move, it was just a dick move.

2008: Jackson attempts to be the hip-hop Donald Trump on 50 Cent: The Money And The Power

Jackson could not resist the tawdry siren song of reality television. But what would his reality show be about? Why money, of course. In 2008, Jackson ripped huge chunks out of the Donald Trump celebrity playbook and launched 50 Cent: The Money And The Power. The show was a knockoff of The Apprentice that found a bunch of hungry hustlers, divided subtly into Team Money and Team Power, competing for the opportunity to win $100,000 and impress Jackson. Trump opined that the show would "fail because (50 Cent is) not Trump," which turned out to be a rare instance of Trump being correct. Usually, not being Trump is a strength; when launching a The Apprentice rip-off, however, it's a weakness. Beyond being nakedly derivative, The Money And The Power was further done in by clumsy plugs for other products in Jackson's media empire, degrading challenges (such as one in which the members of competing teams were shackled together, chain gang style), and competitors who were exactly the kind of loathsome exhibitionists you find on any other reality competition. The show was swiftly canceled due to low ratings, and its failure further diminished the credibility of the 50 Cent brand.

2009: Jackson stars in 50 Cent: Blood On The Sand, a video game set in the Middle East

Like seemingly everything he did circa 2005, Bulletproof, Jackson’s first foray into video games, was a success, selling over a million copies. Bulletproof found 50 and his G-Unit cronies in a comfortably on-brand street-revenge scenario involving Jackson going after the hit men who tried to kill him. But for some reason, the game’s follow-up, 2009’s Blood In The Sand, took the action from the inner city to an unnamed Middle Eastern country, where 50 and his sidekicks are tasked with retrieving a diamond-encrusted skull worth millions. The game got better reviews than Bulletproof, but sold a fraction of what the earlier game did, perhaps because Jackson making a Middle Eastern-set video game about a diamond skull was about as off-brand for the G-Unit head honcho as humanly possible, unless Jackson decided to sponsor an modern improvisational dance troupe.

2009: Jackson goes after Rick Ross, regrets it

Hip-hop’s code of authenticity should have given 50 Cent a huge advantage in his beef with Rick Ross. Jackson had sold crack and been shot multiple times, giving him instant cred, whereas Ross was a morbidly obese Notorious B.I.G. soundalike with a shameful past as a prison guard. That probably explains why Jackson felt confident going after him, but it turned out fans didn’t care about where rappers came from so much as what they were currently doing. Ross’ backstory consequently didn’t matter as much as his ability to crank out the kind of catchy hits Jackson once churned out effortlessly. There was a time when Jackson could have ended Rick Ross’ career with a diss track. Instead, the beef ended up irrevocably harming Jackson’s career: his constant attacks on Ross did nothing to harm the outsized rapper’s ascent to superstardom, while Jackson entered a steep professional downward spiral. In videos on his website and on YouTube, Jackson depicted himself as the champion of the unfortunate women Ross had abandoned and mistreated. To that end, he gives a forum to Ross’ ex Tia, who, in a rant that now feels deliciously ironic given Jackson’s recent woes, tells the camera that Ross was merely feigning wealth with rented jewels and cars. Ever the gentleman, Jackson then pulls out a sleazy skin mag and shows a picture of Lastonia Leviston (or "Brooke" as she is identified in the video), a woman he claims is a call girl (or "really exclusive whore" in his charming turn of phrase) in addition to being the mother of one of Ross’ children. The beef set in motion the chain of events that would lead to Jackson begging for mercy in bankruptcy court, when his undying desire to humiliate Ross led to him leaking a sex tape that ultimately resulted in a costly lawsuit for Jackson.

2009: Jackson introduces Pimpin’ Curly

After ascending to superstardom, Jackson puzzlingly seized upon YouTube as a showcase for his material that just couldn’t wait to go through traditional channels. This mostly consists of homemade videos in which he wears silly costumes, talks in silly voices, and mugs his way through ostensibly comic vignettes. Jackson’s signature YouTube character is Pimpin’ Curly, a procurer of prostitutes with Eriq LaSalle’s hair from Coming To America and a voice out of a blaxploitation movie. Unlike most YouTube videos, 50 Cent’s Pimpin’ Curly videos have millions of views on YouTube (they are also hosted on Jackson’s own website). But otherwise, they're remarkably similar to most other comedy videos on YouTube in that they are a self-indulgent waste of everyone’s time. That especially goes for Jackson himself, who became inexplicably fixated on amateur sketch comedy rather than, say, his music or his family. It’d be tempting to dismiss these curious exercises as harmless ways for Jackson to amuse himself (if only himself) except that Pimpin’ Curly put in a cameo in the leaked sex tape that is the source of his current financial woes.

2009: Jackson writes, directs, and stars in the insane vanity project Before I Self Destruct

Pimpin' Curly wasn't 50's only outlet for his extra-musical creativity. Jackson also took what appeared to be his grandma's camcorder and wrote, directed, and starred in the insanely awful Before I Self Destruct, a DVD of which was included with his album of the same name. Thus Jackson found a way to disappoint fans in multiple media at once with a hilariously inept melodrama about an athlete who gets wrapped up in gang violence in an attempt to provide for his brother, a 12-year-old genius who has already been accepted to every Ivy League institution. Yes, Jackson made a movie where the B plot involves a pint-sized super-genius, and remarkably, that's probably the film's most realistic aspect.

2011: In yet another bid for his non-existent acting career, Jackson co-writes a role for himself as a cancer-stricken college football player in All Things Fall Apart

Jackson didn’t get good roles following Get Rich for an understandable reason: he is a terrible actor incapable of playing a character based on himself, much less anyone else. Eager to broaden his range beyond his default role of "drug dealer in generic thrillers," Jackson took the unusual and extreme step of losing 54 pounds and co-writing and personally financing All Things Fall Apart, in which he plays a college football star who goes from being a serious contender for the Heisman Trophy to being diagnosed with cancer. That is remarkable dedication — especially since Jackson was a 35-year-old man playing a college kid — but even if he was born the same day as his character, he still wouldn’t have been able to sell it. The Raging Bull scary-weight-loss route may work for seasoned actors, but the response to his bid for respectability was the same as all his films: it was barely released in theaters and became a punchline for the critics that Jackson had hoped to impress. With All Things Fall Apart, Jackson tried to establish himself as a serious actor; instead he merely cemented his reputation as a deluded narcissist.

2015: Jackson's leak of a sex tape featuring an ex-girlfriend of Rick Ross costs him in more ways than one

While the path to Jackson’s bankruptcy was long and eventful, the ultimate catalyst was a multi-million-dollar lawsuit Jackson lost against Lastonia Leviston, the ex-girlfriend of rival Rick Ross, who accused Jackson of leaking a sex tape featuring her in an attempt to humiliate her ex-boyfriend back in 2009. The sex tape leak embodies everything that makes Jackson deplorable Leaking the sex tape neatly embodied everything that makes Jackson deplorable: the sociopathic intensity of his beefs, his entitlement, even Pimpin’ Curly, who makes an appearance early in the video through the magic of editing. Maybe Jackson can try to save face and argue that Pimpin’ Curly took over his mind, Jekyll and Hyde style, and made all the terrible mistakes that took his alter-ego from the penthouse to the gutter in 12 tumultuous years. After all, 50 Cent spent much of his career cultivating an image as a cool, collected, consummate businessman not ruled by emotions, and that person clearly could have not have consistently made such awful decisions. Pimpin’ Curly, on the other hand — now that is a man who is not to be trusted.



