50 Cent

On June 29, 1994, Jackson was arrested for selling four vials of cocaine to an undercover police officer. He was arrested again three weeks later, when police searched his home and found heroin, ten ounces of crack cocaine and a starting pistol. Although Jackson was sentenced to three to nine years in prison, he served six months in a boot camp and earned his GED. He has said that he did not use cocaine himself. Jackson adopted the nickname "50 Cent" as a metaphor for change. The name was inspired by Kelvin Martin, a 1980s Brooklyn robber known as "50 Cent"; Jackson chose it "because it says everything I want it to say. I'm the same kind of person 50 Cent was. I provide for myself by any means."

On June 29, 1994, Jackson was arrested for selling four vials of cocaine to an undercover police officer. He was arrested again three weeks later, when police searched his home and found heroin, ten ounces of crack cocaine and a starter's pistol. Although Jackson was sentenced to three to nine years in prison, he served six months in a boot camp (where he earned his high-school equivalency diploma). According to him, he did not use cocaine.

Jackson began rapping in a friend's basement, where he used turntables to record over instrumentals. In 1996, a friend introduced him to Jam Master Jay of Run-DMC, who was establishing Jam Master Jay Records. Jay taught him how to count bars, write choruses, structure songs and make records. Jackson's first appearance was on "React" with Onyx, for their 1998 album Shut 'Em Down. He credited Jam Master Jay for improving his ability to write hooks, and Jay produced Jackson's first (unreleased) album. In 1999, after Jackson left Jam Master Jay, the platinum-selling producers Trackmasters signed him to Columbia Records. They sent him to an upstate New York studio, where he produced thirty-six songs in two weeks; eighteen were included on his 2000 album, Power of the Dollar. Jackson founded Hollow Point Entertainment with former G-Unit member Bang 'Em Smurf.

On October 13, 1996, Jackson's girlfriend, Shaniqua Tompkins, gave birth to son Marquise Jackson. Tompkins later sued Jackson for $50 million, saying he promised to take care of her for life. The suit, with 15 causes of action, was dismissed by a judge who called it "an unfortunate tale of a love relationship gone sour." The two have bickered for years, and have even taken their feud to social media many times.

On May 24, 2000, Jackson was attacked by a gunman outside his grandmother's former home in South Jamaica. After getting into a friend's car, he was asked to return to the house to get some jewelry; his son was in the house, and his grandmother was in the front yard. Jackson returned to the back seat of the car, and another car pulled up nearby; an assailant walked up and fired nine shots at close range with a 9mm handgun. Jackson was shot in the hand, arm, hip, both legs, chest, and left cheek. His facial wound resulted in a swollen tongue, the loss of a wisdom tooth and a slightly slurred voice; his friend was wounded in the hand. They were driven to a hospital, where Jackson spent thirteen days. The alleged attacker, Darryl Baum, Mike Tyson's close friend and bodyguard, was killed three weeks later.

Before he signed with Interscope Records, Jackson engaged in a public dispute with rapper Ja Rule and his label, Murder Inc. Records, saying that a friend robbed jewelry from Ja Rule and the latter accused him of orchestrating the robbery. Ja Rule said that the conflict stemmed from a Queens video shoot, when Jackson did not like seeing him "getting so much love" from the neighborhood. At The Hit Factory in New York in March 2000, Jackson had an altercation with Murder Inc. associates and received three stitches for a stab wound. Rapper Black Child claimed responsibility for the stabbing, saying that he acted in self-defense when he thought someone reached for a gun.

In the hospital Jackson signed a publishing deal with Columbia Records before he was dropped from the label and blacklisted by the recording industry because of his song, "Ghetto Qu'ran". Unable to work in a U.S. studio, he went to Canada. With business partner Sha Money XL, Jackson recorded over thirty songs for mixtapes to build a reputation. In a HitQuarters interview, Marc Labelle of Shady Records A&R said that Jackson used the mixtape circuit to his advantage: "He took all the hottest beats from every artist and flipped them with better hooks. They then got into all the markets on the mixtapes and all the mixtape DJs were messing with them." Jackson's popularity increased, and in 2002 he released the mixtape Guess Who's Back?. He then released 50 Cent Is the Future backed by G-Unit, a mixtape revisiting material by Jay-Z and Raphael Saadiq.

In 2002, Eminem heard Jackson's Guess Who's Back? CD, received from Jackson's attorney (who was working with Eminem's manager, Paul Rosenberg). Impressed, Eminem invited Jackson to fly to Los Angeles and introduced him to Dr. Dre. After signing a $1 million record deal, Jackson released No Mercy, No Fear. The mixtape featured one new track, "Wanksta", which appeared on Eminem's 8 Mile soundtrack. Jackson was also signed by Chris Lighty's Violator Management and Sha Money XL's Money Management Group.

In 2002, Jackson filed an application with the United States Patent and Trademark Office to register the term "50 Cent" as a trademark for clothing, sound recordings, and live performances. The application was published in 2003, and registration issued in 2004. He has since filed for additional trademark registrations.

Jackson and four members of his entourage were arrested shortly before 2 a.m. on December 31, 2002, when police found a .25-caliber handgun and a .45-caliber pistol in a parked car (which they searched due to its tinted windows) outside a Manhattan nightclub. The rapper was charged with two counts of criminal possession of a weapon.

Jackson released his debut album, Get Rich or Die Tryin' (described by AllMusic as "probably the most hyped debut album by a rap artist in about a decade"), in February 2003. Rolling Stone noted its "dark synth grooves, buzzy keyboards and a persistently funky bounce", with Jackson complementing the production in "an unflappable, laid-back flow". It debuted at number one on the Billboard 200, selling 872,000 copies in its first four days. The lead single, "In da Club" (noted by The Source for its "blaring horns, funky organs, guitar riffs and sparse hand claps"), set a Billboard record as the most listened-to song in radio history within a week.

Interscope gave Jackson his own label, G-Unit Records, in 2003. He signed Lloyd Banks, Tony Yayo and Young Buck as members of G-Unit, and The Game was later signed in a joint venture with Dr. Dre's Aftermath Entertainment. In March 2005, Jackson's second commercial album, The Massacre, sold 1.14 million copies in its first four days (the highest in an abbreviated sales cycle) and was number one on the Billboard 200 for six weeks. He was the first solo artist with three singles in the Billboard top five in the same week with "Candy Shop", "Disco Inferno" and "How We Do". According to Rolling Stone, "50's secret weapon is his singing voice - the deceptively amateur-sounding tenor croon that he deploys on almost every chorus".

Jackson has had a highly successful business career. He is financially invested in a highly diversified variety of industries. Jackson is now involved in artist and talent management, record, television, and film production, footwear, apparel, fragrances, liquor, video games, mobile apps, book publishing, headphones and health drinks and dietary supplements. His broad business and investment portfolio contains investments in a variety of sectors including real estate, financial market investments, mining, boxing promotion, vodka, fragrances, consumer electronics and fashion. He established his own record label G-Unit Records in 2003 following his mainstream success. In November 2003, he signed a five-year deal with Reebok to distribute a G-Unit Sneakers line for his G-Unit Clothing Company. In an interview, Jackson said his businesses had a habit of doing well as he saw all of his ventures both past and present as revolving around his alter ego. Jackson has also started a book publishing imprint, G-Unit Books on January 4, 2007 at the Time Warner Building in New York. He has written a number of books including a memoir, From Pieces To Weight in 2005 where it sold 73,000 copies in hardcover and 14,000 copies in paperback; a crime novel and a book with Robert Greene titled The 50th Law, an urban take on The 48 Laws of Power. In November 2011, Jackson released 50 Cent's Playground, a young adult fiction novel about a bullied, violent boy and his gay mother.

Jackson has founded two film production companies: G-Unit Films in 2003 and Cheetah Vision in 2008. Cheetah Vision produces low budget action thrillers for foreign film markets across the world. When G-Unit Films folded, he focused on Cheetah Vision and the company obtained $200 million in funding in 2010. In 2010, Jackson revived G-Unit Films, renaming the company to G-Unit Films and Television Inc. The company has joint ventures with Will Packer's production company Will Packer Productions and Universal Television. In over 18 months, Jackson has sold projects to six different networks. Among them was Power, a STARZ drama in which he not only co-stars but also serves as co-creator and executive producer. Power debuted in June 2014 and was renewed for a second season after one episode. Power's August 2 season finale garnered the high ratings through the season, more than doubling the premiere and it generated 71% of the African-American viewership of any scripted premium series since 2006. Jackson serves as a co‐star, co-creator and executive television producer of the STARZ network drama where he signed a 2-year contract with representation coming from the Agency for the Performing Arts. Ratings have been a success for Starz. with the second-season premiere being the highest-ever season with 1.43 million people tuning in live. Jackson also serves as an executive television producer for Dream School for SundanceTV, a series that follows fifteen high school dropouts as they are taught by a series of celebrity "teachers".

One of Jackson's first business ventures was a partnership with Glacéau to create an enhanced water drink called Formula 50. In October 2004, Jackson became a beverage investor when he was given a minority share in the company in exchange for becoming a spokesperson after learning that he was a fan of the beverage. The health conscious Jackson noted that he first learned of the product while at a gym in Los Angeles, and stated that "they do such a good job making water taste good." After becoming a minority shareholder and celebrity spokesperson, Jackson worked with the company to create a new grape flavored "Formula 50" variant of VitaminWater and mentioned the drinks in various songs and interviews. In 2007, Coca-Cola purchased Glacéau for $4.1 billion and, according to Forbes, Jackson, who was a minority shareholder, earned $100 million from the deal after taxes. Though he no longer has an equity stake in the company, Jackson continues to act as a spokesperson for VitaminWater, supporting the product including singing about it at the BET Awards and expressing his excitement over the company's continuing to allow his input on products. He joined Right Guard to introduce a body spray (Pure 50 RGX) and endorsed Magic Stick condoms, planning to donate part of their proceeds to increasing HIV awareness. Jackson signed a multi-year deal with Steiner Sports to sell his memorabilia, and announced plans for a dietary-supplement company in conjunction with his film Spectacular Regret in August 2007.

In 2005, Jackson supported President George W. Bush after rapper Kanye West criticized Bush for a slow response to the victims of Hurricane Katrina. If his felony convictions did not prevent him from voting, he said, he would have voted for the president. Jackson later said that Bush "has less compassion than the average human. By all means, I don't aspire to be like George Bush." In September 2007 he told Time that although he would not endorse a candidate in 2008, he "liked Hillary [Clinton]". Six months later the rapper told MTV News that he had switched his support to Barack Obama after hearing him speak, but had lost interest in politics. Asked his opinion of President Obama's May 9, 2012 endorsement of gay marriage, Jackson said, "I'm for it ... I've encouraged same-sex activities. I've engaged in fetish areas a couple times." He had been criticized for anti-gay comments in the past.

Jackson was sentenced to two years' probation on July 22, 2005 for a May 2004 incident, when he was charged with three counts of assault and battery after jumping into an audience when he was hit by a water bottle.

In October 2006, The Game made a peace overture (which was not immediately answered) to Jackson, but two days later he said on Power 106 that the peace offer was valid for only one day. In several songs on Doctor's Advocate, he implied that the feud was over. He said in July 2009 that the feud had ended with help from Michael Jackson and Diddy, and apologized for his actions. According to Tony Yayo, neither Jackson nor G-Unit accepted his apology and The Game has resumed his calls for a "G-Unot" boycott at concerts. Jackson released "So Disrespectful" on Before I Self Destruct, targeting Jay-Z, The Game and Young Buck. The Game responded with "Shake", poking fun at the music video for Jackson's "Candy Shop".

In September 2007 Jackson released his third album, Curtis, which was inspired by his life before Get Rich or Die Tryin'. It debuted at number two on the Billboard 200, selling 691,000 copies during its first week. It sold behind Kanye West's Graduation, released the same day; the outcome of this highly-publicized sales battle between Jackson and West has been accredited to the commercial decline of the gangsta rap and "bling era" style that previously dominated mainstream hip-hop.

Forbes noted Jackson's wealth in 2007, ranking him second behind Jay-Z in the rap industry. He lives in a Farmington, Connecticut, mansion formerly owned by ex-boxer Mike Tyson, listing it for sale at $18.5 million to move closer to his son (who lives on Long Island with his ex-girlfriend). The mayor of Bridgeport, Connecticut declared October 12, 2007 "50 Cent Curtis Jackson Day", honoring the rapper with a proclamation and a key to the city. One of Jackson's New York homes, purchased in January 2007 for $2.4 million and the center of a lawsuit between Jackson and Shaniqua Tompkins, caught fire on May 31, 2008 while he was filming in Louisiana.

Jackson filed a lawsuit against an advertising company, Traffix of Pearl River, New York, on July 21, 2007, for using his image in a promotion he said threatened his safety. He was alerted by a staff member to an Internet advertisement on a Myspace page. According to court documents, the advertisement had a cartoon image of the rapper with "Shoot the rapper and you will win $5000 or five ring tones guaranteed". Although the ad did not use his name, the image allegedly resembled him and suggested that he endorsed the product. The lawsuit, calling the ad a "vile, tasteless and despicable" use of Jackson's image which "quite literally call[ed] for violence against him", sought unspecified punitive damages and a permanent injunction against the use of his image without permission.

One of his New York homes, purchased for $2.4 million in January 2007 and the center of a lawsuit between Jackson and Shaniqua Tompkins, caught fire on May 30, 2008 while he was filming in Louisiana. On August 5, 2013, Jackson pleaded not guilty to one count of domestic violence and four counts of vandalism in a Los Angeles County court. If convicted of all charges, he faced up to five years in prison and a $46,000 fine. Model-actress Daphne Joy accused Jackson of kicking her and ransacking her bedroom during an argument at her condominium in the Toluca Lake neighborhood of Los Angeles on June 23. He allegedly caused $7,100 in property damage, leaving the scene before police arrived.

Over the years, Jackson invested his earnings from music and celebrity endorsements in an array of privately controlled companies, real estate, and stocks and bonds. A portion of his investments lost value during the 2008 recession. In December 2008 he told the Canadian press that he had been affected by the recession, losing several million dollars in the stock market. Unable to sell his Connecticut mansion, Jackson postponed Before I Self-Destruct due to the severity of the economic downturn. His Farmington mansion located on 50 Poplar Hill Drive that he tried to sell for years filed for bankruptcy in Connecticut in 2015 listed an asking price for that property in 2012 at $10 million but was valued at $8.3 million in 2015. He first tried to sell the house in 2007 for $18.5 million, and dropped the price several times in the next five years, when it was on and off the market. In January 2011, Jackson reportedly made $10 million after using Twitter to promote a marketing company which he was part shareholder of. His endorsements company G Unit Brands Inc. revealed through a public SEC filing controls 12.9 per cent of H&H Imports, which is a parent company of TV Goods – the firm responsible for marketing his range of headphones, Sleek by 50 Cent. Jackson bought stock in the company on November 30, 2010, a week after it offered buyers 180 million shares at 17 cents each. Jackson later made a stock recommendation on Twitter, causing its share value to rise from four cents to nearly 50 cents (32p) each, closing on Monday at 39 cents (25p). Jackson was later investigated by the Securities and Exchange Commission for breaching securities laws following his tweet which may have constituted allegations of Insider trading via his Pump and dump stock investment strategy. In 2013, Jackson became a minority investor in Hang w/, a live video broadcasting mobile app used by dozens of celebrities to broadcast their daily activities and chat with fans. The app was downloaded more than 1 million times since its launch in March 2013 and had more than 1 million users as of February 2015. Other minority celebrity investors include former NFL player Terrell Owens and record producer Timbaland.

In 2008, Jackson visited a platinum, palladium and iridium mine shaft in South Africa, and met with South African billionaire Patrice Motsepe in talks of purchasing an equity stake in the mine. After his meeting with Motsepe, Jackson considered purchasing equity in the mine and launching his own line of 50 Cent branded platinum.

Marquise's birth changed Jackson's outlook on life: "When my son came into my life, my priorities changed, because I wanted to have the relationship with him that I didn't have with my father". He credited his son for inspiring his career and being the "motivation to go in a different direction". Despite this, the two have endured a fractured relationship that began when Jackson and Tompkins separated in 2008. Their feud has been taken to social media numerous times, including in 2020 when Jackson disclosed that he "used to" love his son. Jackson has a tattooed "Marquise" with an axe on his right biceps ("The axe is 'cause I'm a warrior. I don't want him to be one, though"), and has "50", "Southside" and "Cold World" on his back: "I'm a product of that environment. It's on my back, though, so it's all behind me".

In December 2008, he told the Canadian press that he had lost several million dollars in the stock market and, unable to sell his Connecticut mansion, had postponed Before I Self-Destruct because of the economic downturn. Jackson won a lawsuit in November 2009 against Taco Bell over the fast-food chain's use of his name without permission.

In 2008, Jackson sued Taco Bell over an ad campaign in which it invited him to change his name for one day from 50 Cent to 79 Cent, 89 Cent, or 99 Cent, in line with pricing for some of its items, and they would donate $10,000 to the charity of his choice. The case was settled out of court.

On the September 10, 2008 episode of Total Request Live Jackson said his fourth studio album, Before I Self Destruct, would be "done and released in November". He released "Ok, You're Right", produced by Dr. Dre for Before I Self Destruct, on May 18, 2009 and was scheduled to appear in a fall 2009 episode of VH1's Behind the Music. On September 3, 2009 Jackson posted a video for the Soundkillers' Phoenix- produced track, "Flight 187", introducing his mixtape and book (The 50th Law). The song, with lyrics inspiring speculation about tension between Jackson and Jay-Z, was a bonus track on the iTunes version of Before I Self Destruct. Before I Self Destruct was released on November 9, 2009.

Before leaving for Venezuela, Jackson uploaded a video ("Warning Shot") and the first of a series of "Officer Ricky" cartoons. In early February he uploaded a YouTube video in which he interviewed "Tia", the mother of one of Ross' children; according to her, Ross is in reality a correctional officer. On February 5, 2009, The Game phoned Seattle radio station KUBE. Asked about the dispute between Jackson and Ross, he sided with Jackson and offered to mediate: "Rick Ross, holla at your boy, man" and "50 eating you, boy."

In a Contactmusic.com interview, Jackson said he was working on a Eurodance album, Black Magic, inspired by European nightclubs: "First they played hip-hop which suddenly changed to uptempo songs, known as Eurodance". He later said he had changed his next album to The Return of the Heartless Monster after writing different material when he returned home from the Invitation Tour in 2010, shelving Black Magic. On September 3, Jackson supported Eminem on his and Jay-Z's The Home & Home Tour, performing "Crack A Bottle" with Eminem and Dr. Dre amid rumors of tension between Jackson and Dre.

He "recorded 20 songs to a whole different album concept" before putting them aside, wanting his new album to have the "aggression" of Get Rich or Die Tryin'. Jackson tweeted that the album was "80 percent done" and fans could expect it in the summer of 2011. It was ultimately delayed a year due to disagreements with Interscope Records, with Jackson saying that he would release it in November 2011 with a different title than Black Magic. Eminem would appear on the album, and Jackson said he was working with new producers such as Boi-1da and Alex da Kid. Cardiak, who produced Lloyd Banks' "Start It Up", confirmed that he produced a song for the upcoming album.

Jackson released a song, "Outlaw", from his fifth album on the Internet on June 16, 2011. The single, produced by Cardiak, was released on iTunes on July 19 (although Jackson tweeted that it was not the album's first single). The rapper planned to write a semi-autobiographical young-adult novel about bullying, different from his previous books which focused on his life and the rules of power. According to the book's publisher, the first-person novel (about a 13-year-old schoolyard bully "who finds redemption as he faces what he's done") was scheduled for publication in January 2012.

In a series of tweets Jackson told that the delay of his fifth album was due to disagreements with Interscope Records, later suggesting that it would be released in November 2011 with his headphone line (SMS by 50). He speculated to MTV News about not renewing his five-album contract with Interscope: "I don't know ... It will all be clear in the negotiations following me turning this actual album in. And, of course, the performance and how they actually treat the work will determine whether you still want to stay in that position or not."

On June 20, 2011, Jackson announced the release of Before I Self Destruct II after his fifth album. Although he planned to shoot a music video for the fifth album's lead single, "I'm On It", on June 26 the video was never filmed. Jackson told Shade45, "I did four songs in Detroit with Eminem. I did two with Just Blaze, a Boi-1da joint, and I did something with Alex da Kid. We made two that are definite singles and the other two are the kinds of records that we been making, more aimed at my core audience, more aggressive, more of a different kind of energy to it." He released "Street King Energy Track #7" in September 2011 to promote Street King, his charity-based energy drink. An announcement that Jackson was shooting a music video for "Girls Go Wild", the fifth-album lead single featuring Jeremih, was made on September 28, 2011.

In July 2011, Jackson launched a philanthropic initiative to provide food for one billion starving people in Africa by 2016, joining Pure Growth Partners to introduce Street King. A portion of the proceeds from each Street King purchase would be used to provide a daily meal to an underprivileged child. The partnership coincides with Jackson's goal to feed a billion people in Africa during the next five years. "50 Cent and I share a common vision: to address the world's problems through smart and sustainable business models," said Chris Clarke, founder and CEO of Pure Growth Partners. "With the rampant starvation in Africa and hunger afflicting children worldwide, we need socially responsible businesses that affect real change now more than ever." Jackson said, "I'm inspired by Clarke's vision and innovative approaches to tackling serious issues. It's our mission with Street King to really change children's lives around the world." In 2011, he founded SMS Audio, a consumer-electronics company selling Street by 50 headphones, pledging to donate a portion of their sales to charity. In April 2015, SMS announced new co-branding deals with Reebok and Marvel. It added those to existing partnerships with Walt Disney Parks, Lucasfilm's Star Wars, and Intel.

The end of the Jackson-Ja Rule feud was confirmed in May 2011. According to Ja Rule, "I'm cool. We ain't beefing no more. We'll never collaborate. That's just what it is. You don't have to be at war with somebody, but it's also kind of like U.S. and another country that they may not get along with. We don't gotta go to war, but we're not friends either. But we can coincide inside of a world. He's doing him, and he's not thinking about me, and I'm doing me and I'm not thinking about him."

Jackson's fifth album, Street King Immortal, was initially scheduled for a summer 2012 release and postponed until November 13. Disagreements with Interscope Records about its release and promotion led to its temporary cancellation. Its first promo single, "New Day" with Dr. Dre and Alicia Keys, was released on July 27. The song was produced by Dr. Dre, mixed by Eminem and written by 50 Cent, Alicia Keys, Royce da 5'9" and Dr. Dre. A solo version by Keys was leaked by her husband, Swizz Beatz. "My Life", the album's second promo single (with Eminem and Maroon 5 lead singer Adam Levine), was released on November 26, 2012.

On July 21, 2012, Jackson became a licensed boxing promoter when he formed his new company, TMT (The Money Team). Licensed to promote in New York, he was in the process of being licensed in Nevada (where most major fights are held in the U.S.). A former amateur boxer, Jackson signed gold medalist and former featherweight champion Yuriorkis Gamboa and middleweight Olympic medalist Andre Dirrell. On July 29, 2012, he and the boxer Floyd Mayweather, Jr., signed IBF featherweight champion Billy Dib. They unveiled plans to challenge the box-office dominance of mixed martial arts and change the landscape of boxing with TMT Promotions. Boxer Zab Judah also expressed interest in making a deal with Jackson. In December 2012, Mayweather and Jackson parted company, with Jackson taking over the promotion company and founding SMS Promotions with Gamboa, Dirrell, Dib, James Kirkland, Luis Olivares and Donte Strayhorn in his stable.

Jackson dated model Daphne Joy and had his second son, Sire Jackson, with her, on September 1, 2012. At the age of two years, Sire modeled for Kidz Safe, a headphone brand for kids, earning $700,000 through his contract.

On his album Deeper Than Rap, Ross refers to Jackson in "In Cold Blood" and Jackson's mock funeral is part of the song's video. When the song was released, Ross said that he ended Jackson's career. "Rick Ross is Albert From CB4. You ever seen the movie? He's Albert," Jackson replied in an interview. "It never gets worse than this. You get a guy that was a correctional officer come out and base his entire career on writing material from a drug dealer's perspective such as "Freeway" Ricky Ross." Their feud rekindled at the 2012 BET Hip Hop Awards, where Jackson and G-Unit members Kidd Kidd, Mike Knox, Tony Yayo were seen on video attacking Gunplay (a member of Ross' Maybach Music Group). Gunplay's Maybach Music diamond necklace was stolen during the brawl, and several days later Jackson appeared at a Washington, D.C. bowling alley wearing Gunplay's chain. On January 30, 2013, Jackson tweeted that Ross' attempted drive-by shooting on his birthday three days earlier was "staged".

In January 2014, Jackson said he planned to release Animal Ambition in the first quarter of the year, followed by Street King Immortal. On February 20 he left Shady Records, Aftermath Entertainment and Interscope, signing with Caroline and Capitol Music Group. According to Jackson, although he owed Interscope another album he was released from his contract because of his friendship with Eminem and Dr. Dre: "I'm a special case and situation. It's also because of the leverage of having the strong relationships with Eminem and Dr. Dre. They don't want me to be uncomfortable. They value our friendship to the point that they would never want [to jeopardize] it over that little bit of money."

In 2014, Jackson became a minority shareholder in Effen Vodka, a brand of vodka produced in the Netherlands, when he invested undisclosed amount in the company Sire Spirits LLC. He currently endorses the product via his live concert performances and social media. The rapper was asked to take part in two promotional bottle signings, one in Oak Creek and another in Sun Prairie. Jackson made an appearance at Liquor Warehouse in Syracuse, New York on April 25, 2015 where he reportedly sold 1,400 bottles (277 gallons) of Jackson's signature liquor brand. Liquor Warehouse's owner George Angeloro reportedly stocked 300 cases (1,800 bottles or 357 gallons) of Effen Vodka, which sells for $30 a bottle, prior to the event.

In December 2014, Jackson signed a $78 million deal with FRIGO Revolution Wear, a luxury underwear brand. The joint venture is partnered between Jackson, basketball player Carmelo Anthony, baseball player Derek Jeter and Mathias Ingvarsson, the former president of mattress company Tempur-Pedic. Jackson became the chief fashion designer for the brands single pair of Frigo boxers. In April 2015, Jackson mulled investing in Jamaica, exploring foreign investment opportunities on the island when he met with some local officials and had ongoing discussions on investment opportunities in the Montego Bay resort area.

On May 14, 2015, Jackson revealed in an interview that the first single from Street King Immortal, would be previewed Memorial Day weekend and would likely be released in June. Jackson released "Get Low" on May 20, 2015, as the intended first single from his sixth studio album, Street King Immortal (2015). The song, produced by Remo the Hitmaker, features vocals from fellow American rappers 2 Chainz and T.I., as well as American singer Jeremih. He announced bankruptcy on July 13, 2015.

On July 13, 2015, Jackson filed for Chapter 11 bankruptcy protection in the U.S. Bankruptcy Court for the District of Connecticut with a debt of $32,509,549.91. On July 17, 2015, the Court issued an order allowing a creditor to proceed with the punitive damages phase of a trial against Jackson in a New York state court, in connection with the alleged release of a private video. His assets were listed as between $10 million and $50 million in his bankruptcy petition, though he testified under oath that he is worth $4.4 million. Citing between $10 million and $50 million in debt, and the same amount in assets. Later in the week, Jackson's bankruptcy lawyers elucidated the court documents that legal fees and judgments exceeding $20 million over the past year were the primary cause of the filing.

On August 7, 2015, the feud between the two rappers later reignited when Ja Rule gave a feedback to a social follower via Twitter over a similar feud between Meek Mill and Drake. Enraged, Jackson later responded with photos and comments via Instagram, only siding with Drake. The feud resurfaced three years later on January 19, 2018, when Ja Rule took to Twitter, calling out 50 Cent on social media. 50 cent responded by purchasing and vacating the first four rows of his concert.

In 2016, regarding his beef with Meek Mill, he commented, "You know, he's really not that bright. The easiest thing you can do is bring other people into the statements you're saying, right, while you're writing music." On May 4, 2016, after making fun of a teenager who, unbeknownst to Jackson, had a disability, he donated $100,000 to Autism Speaks.

While walking through Cincinnati/Northern Kentucky International Airport in May 2016, Jackson harassed and insulted a janitor at the airport, accusing him of being under the influence. The janitor was a hearing-impaired, autistic teenager named Andrew Farrell. The parents of the janitor had seen the viral video as disrespect and wanted to sue Jackson for his action against their child. The lawsuit was originally over one million dollars, but the parents settled for a $100,000 donation to Autism Speaks and his apology.

In 2016, a judge declared that Brandon Parrott gave Dr. Dre and 50 Cent the rights to "Bamba" for the song "P.I.M.P."

Judge Ann Nevins has ordered Jackson back to court because of Instagram messages he made over several months. She said Jackson was not fully clear about his funds and indicated posts of the rapper showing stacks of his money. In March 2016, Jackson claimed that he would no longer use Instagram, electing instead to have his profile page operated by someone else.

On August 1, 2016, 50 Cent ended his twelve-year feud with The Game when the two were in the Ace of Diamonds Strip Club and The Game said "What happened, that shit was 12 years ago."

On March 31, 2017, Interscope Records released 50 Cent's final album for the label, a greatest hits album titled Best Of.

On June 25, 2019, The New York Times Magazine listed 50 Cent among hundreds of artists whose material was reportedly destroyed in the 2008 Universal fire.

In 2020, Jackson helmed the executive-producer duties for late rapper Pop Smoke's debut album, Shoot for the Stars, Aim for the Moon, having being one of Pop Smoke's biggest inspirations. The album was released on July 3, 2020. Jackson curated the album, desiring to finish it after Pop had died. He contacted many of the artists involved, and also features on one of the album tracks, "The Woo", which became a top ten single.

Jackson endorsed Democratic candidate Hillary Clinton in the run-up for the 2016 U.S. presidential election. He rejected an offer of $500,000 from the Trump campaign to make an appearance on the candidate's behalf. However, he endorsed Donald Trump in 2020, due to his dislike of Joe Biden's tax plans. A week later, he retracted his endorsement, saying on Twitter "F--k Donald Trump, I never liked him.", and endorsed Biden.

On August 9, 2020, 50 Cent and Rick Ross ended their feud