Before making it big and living it up in Hollywood, some of your favourite artists and actors had to sell drugs just to make ends meet. Some would take the “street” route – hustling on a corner of a store, waiting for customers to spread their business by word of mouth, praying that they wouldn’t be caught by the police. Others operated on a much larger scale – moving bigger quantities of schedule 1 narcotics over the border, serving a much more lucrative market.
As you read this article you’ll notice that a good percentage of the celebrities listed here come from the hip hop industry. This should come as no surprise, considering how popular the theme of ‘drugs and money’ is in rap culture. That said, other celebrities on this list will blow you away.
While some of these now-stars managed to hustle and grind without ever getting caught, others weren’t so lucky and ended up facing jail time. For most, jail time served as a wake-up call and led to them to pursue other (more legitimate) entrepreneurial avenues. In many cases, their inherent business-minded attitudes have helped kickstart their pop-culture careers, making them much more money than selling drugs ever did.
#25 – Bon Jovi
Born John Francis Bongiovi Jr. in Perth Amboy, New Jersey, the entertainer had a fairly average upbringing. He did all of the things you expect from kids and didn’t really come into his own until his early teens. By this time, John was hanging out at local clubs and was imagining his life as a rockstar. He began to act on his dream, and by the time he turned 16, he was already playing in clubs.
While in his teens, Bon Jovi also tried to make a few bucks by selling marijuana. He admits to buying a few quarter pounds of dope with the intent of “chopping it up” and selling at a profit. “I was entrepreneurial even then,” says the star.
At that time, Bon Jovi also smoked a fair bit of weed himself, and even admitted to smoking dope laced with “PCP.” Luckily, the singer decided that the whole ‘drug thing’ wasn’t working out for him, and started to channel his energy into music instead. Hard to argue against his decision, considering the superstar sold over 120 million albums since becoming an international sensation in the early 80s.
#24 – Mark Wahlberg
Mark Wahlberg is arguably one of the most talented people in Hollywood. From headlining Marky Mark and the Funky Bunch, to underwear modeling, to his outstanding acting career, Wahlberg has seemingly done it all. Although he is currently a devout Christian, Wahlberg wasn’t always so well behaved. His early years have earned him somewhat of a “bad boy” reputation, which also stuck around for his Hollywood days.
Wahlberg grew up the youngest of nine children in Dorchester, Massachusetts, where he had a troubling upbringing. Having dropped out of school at just fourteen, Wahlberg got involved with some questionable crowds. After deciding that school wasn’t panning out, he became a gang affiliate and picked up a cocaine habit.
During his early teens, Mark had somewhere between 20 and 25 run-ins with the law, including a 45-day jail term at age 16 for selling drugs (amongst other things). This experience acted as a wake-up call, and after his release, Mark began to turn his life around. With the help of his older brother, he got involved with rap and eventually transitioned into a successful Hollywood actor with projects like Lone Survivor (2013) and Ted 2 (2015) under his belt.
#23 – Idris Elba
He might have won a Golden Globe for his detective role on the British crime drama “Luther,” but ironically, the star had quite a bit of trouble with the law himself. Before becoming one of the hottest actors in Hollywood (best known for his role on The Wire) Elba had to overcome many challenges to get where he is today.
In a GQ interview, the 41-year-old actor opened up about selling drugs after coming to New York City from the UK. Elba’s story fits the mold of the classic American dream tale, where a struggling actor spends his days looking for auditions while working odd jobs.
Before landing his first acting gig in the US, Elba was DJ’ing, while at the same time selling weed. Elba admitted to dealing at the same club he worked at but said that he needed to do what he did in order to survive. At the time, the superstar spent a lot of his nights sleeping in his Astro van, so money was obviously a problem. Fortunately, Elba managed to turn his life around and now earns an honest living doing what he loves most.
#22 – Notorious B.I.G
Christopher Wallace, Biggie, or the Notorious B.I.G is still widely ranked as one of the most influential rappers of all time. Born in Brooklyn to a Jamaican preschool teacher, Biggie had a fairly rough childhood. His father abandoned him and his mother, Voletta Wallace, when he was just two years old. The unfortunate circumstance forced his mom to take on a second job in order to put food on the table. She continued to work multiple jobs to make ends meet, but as Biggie started to grow up he was also growing more and more dissatisfied with life in the lower class.
In his early teenage years, Biggie turned to the drug trade, selling everything from marijuana to cocaine in order to put some cash in his pockets. He and a few friends would take up spots all over Brooklyn, servicing clients from every walk of life. Biggie managed to make quite a bit of cash through his illicit activities, but eventually his party ended when his mom found a stash of cocaine under his bed.
She kicked him out of her home, and shortly after Biggie was arrested for drug dealing and was locked up for a 9-month stretch. Unfortunately the rapper never did manage to turn his life around, as he was murdered at an age of 24.
#21 – Snoop Dogg
Snoop Dogg has earned himself quite the reputation for the amount of marijuana that he consumes on a regular basis. In a recent Reddit AMA thread he said that he smokes “81 blunts x 7,” when asked how much weed he smokes a week. That’s right, 81 joints every single day – or so he says. Even if this figure is inflated, there is no doubting Snoop’s commitment to the plant.
Last year, the platinum-selling musician started his own brand of marijuana. ‘Leafs by Snoop’ went on sale in Colorado back in 2015 and Snoop believes that it will become the first mainstream cannabis brand in the world. Interestingly enough, he isn’t able to legally own his own brand since he isn’t a Colorado resident.
Although he now holds a medical marijuana card, allowing him the right to purchase at any given time, Snoop wasn’t always smoking legally. According to Cameron Diaz, who went to the same high school as Snoop, he smoked and sold a lot of marijuana. The actress also admits to becoming a regular customer herself. “He was tall and skinny. I’m pretty sure I bought weed from him,” says Diaz.
#20 – Jay-Z
Jay-Z is not so much a rapper as he is a businessman. Today, Jay-Z is half of the richest celebrity couple in the world – together with Beyonce he’s worth over a billion dollars. Jay managed to amass such an impressive net worth thanks to his successful hip-hop career, numerous endorsements, and many entrepreneurial ventures. Just 25 years ago, however, Sean Carter was just another teenager trying to survive by selling drugs in Brooklyn.
Hustling since an early age, Carter made a name for himself in his borough by selling everything from marijuana to crack cocaine. Jay says that his mother knew what he was doing, but chose to look the other way because putting food on the table was difficult at times. Although Jay-Z moved a fair bit of product, he says that he never used any of it himself.
While dealing drugs often results in serious consequences, the rapper says that it actually helped him better understand business. In a Vanity Fair interview a few years back, Jay-Z says that selling drugs taught him the basics of budgeting. “You need to know what you can spend [and] what you need to re-up,” says the music mogul.
#19 – Kid Rock
Like a lot of other musicians, Kid Rock released a lot of music that went nowhere. After about a decade of treading in place and releasing music that no one wanted, Kid Rock announced his fourth album titled Devil without a Cause, and proclaimed that he will be “going platinum.” Turns out the album was indeed riddled with instant classics, allowing Kid Rock to deliver on his promise in 1999. He went on to have a successful music career, amassing a net worth of more than $80 million.
Despite his current wealth, things weren’t always so easy for the singer-songwriter. Like a number of other ‘troubled artists,’ Kid Rock had a fairly rough upbringing. At the age of 15, he ran away from home and joined a gang called ‘Best Friends’. Through this gang, he began dealing drugs, earning himself a comfortable living.
Who knows where Kid Rock would end up had it not been for a local man interested in keeping teens out of trouble. One day he approached the gang and offered them to open for his band, “The Beast Crew.” Kid Rock agreed, and after performing at several shows, a producer (D-Nice) set up a meeting with Jive Records. After hearing some of his music, Jive offered Kid a record deal that same day, kickstarting his career.
#18 – T.I.
Before Clifford Joseph Harris Jr. was known as T.I. he had a nickname of Rubber Band Man, which was a reference to the rubber bands he wore on his wrist (which symbolize wealth). As a young teen, T.I. made a decent living by dealing drugs on the streets of Atlanta, and by the time he turned 14 he was already arrested several times. Despite the numerous arrests, T.I. continued to have more run-ins with the law over the next few years.
In an interview back in 2007, T.I. explained that (among other crimes) he dealt drugs as a means to garner independence. He claims that selling drugs helped put food on the table for him and his mother, as his father wasn’t around and did not provide for the family.
Luckily, the rapper managed to turn his life around and become a legitimate entrepreneur instead. Aside from rapping, T.I. has been involved in a number of community efforts – most notable of which was his involvement post Hurricane Katrina. Today, the rapper is still doing what he loves, and his passion earned him a net worth of approximately $50 million.
#17 – 50 Cent
Although 50 Cent received a lot of recognition on the underground hip-hop circuit, he remained relatively unknown for several years. In 2002, one of his singles, “Wanksta,” appeared on the soundtrack of 8 Mile, and his career started to take off. A year later he released his first studio album titled Get Rich or Die Tryin’, which quickly topped the charts and broke sales records.
Today, 50 Cent owns his own record label and is worth north of $150 million. That said, things weren’t always so peachy for the Queens rapper. Growing up in South Jamaica, 50 Cent was constantly exposed to gang violence and often surrounded by criminals. When 50 Cent was born, his mother, Sabrina Jackson, was only 15 years. Having no way to support her newborn, Sabrina turned to dealing drugs to earn a living. Over the next half decade, Sabrina became one of the best known and most feared drug dealers in Queens. Shortly after 50 Cent turned 8, his mother was mysteriously killed, likely as a result of her involvement with drugs.
Growing up with his grandmother, 50 Cent spent a lot of time on the streets – surrounded by questionable role models. By the time he was 12, 50 Cent started dealing crack to help his grandmother support the other nine children in her care.
#16 – Sam Hurd
Sam Hurd is not a ‘celebrity’ in the pop-culture, Hollywood, way, but he’s definitely worthy of mentioning. For those that don’t follow American football, Hurd is a former wide receiver that played in the NFL for six seasons. He had a very promising career ahead of him until he was arrested on federal drug charges, effectively sabotaging his own professional success.
Despite securing a multi-million dollar contract with the Chicago Bears, Hurd just couldn’t get enough. In 2011 he was arrested for an attempt to purchase and distribute as much as 1,000 pounds of marijuana and more than 20 pounds of cocaine each week. Unfortunately for Hurd, this deal happened with an undercover police officer – securing himself an investigation into his connection to the drug trade.
While awaiting trial on these charges, Hurd couldn’t resist the temptation of buying more drugs, a decision that got him busted in 2012. This move resulted in him being jailed indefinitely, until finally being sentenced to a 15-year stint at the Texas penitentiary in 2013. Last year, Hurd’s defense filed a motion to have his sentence reduced to 9 years, but it’s unclear whether or not they’ll be successful. Worst case scenario, Hurd will be 40 when he gets out of prison.
#15 – Frank Ocean
Frank Ocean is widely regarded as one of the best singer-songwriters in the industry. Although he was born in Long Beach, California, his family moved to New Orleans when he was a child. Ocean grew up there, being surrounded by the local jazz scene. He say’s that it was the jazz, along with this mother’s R&B CDs that have instilled a passion for music within him.
Ocean began writing and recording music while in high school. High school was a rough time period for the musician, and he admits to dealing drugs. Ocean says that “he didn’t know any better,” due to the lack of a strong father figure in his life. He used his illicit earnings (along with anything else he made doing odd jobs) to pay for studio time – chasing his dream. He didn’t fully commit to making music until Hurricane Katrina wreaked havoc on the region. During the disaster, his studio was flooded and robbed, which prompted him to set aside his education and pursue his music goals instead.
Today Frank Ocean leads a life that many musicians only dream of. He writes lyrics for world-renowned superstars like Jay-Z and Beyonce, while at the same putting out music of his own.
#14 – Brandi Brandt
Brandi Brandt is the first woman on this list, and although she is not a celebrity in a traditional sense, she was a popular Playboy model in the late 80s. Brandi was widely adored by men and women from all over the world, especially after featuring as the Playmate of the Month in October of 1987.
Almost exactly 20 after her centerfold, Brandi was arrested for dealing drugs. In this case, Brandi wasn’t just selling a few grams of weed here and there, but she was alleged to have been involved in a massive cocaine trafficking syndicate that was importing drugs into Australia.
After her arrest, Brandt was extradited to Sydney, Australia where she had to defend her charges in a Sydney court. On the recommendation of her council, Brandt plead guilty to the charge of conspiracy to import drugs and was sentenced to six years in prison. So far she has served two years of her sentence, and due to her good behavior, she will be eligible for parole this November.
#13 – Meek Mill
Meek Mill is a 29-year-old rapper from Philadelphia. The young hip-hop star captured the spotlight in 2012 after the debut of his first studio album, Dreams and Nightmares, which was released under Warner Bros. Records. The album debuted at number 2 on the Billboard 100 and remained there for quite some time.
While a vast majority of hip-hop artists just rap about selling drugs, Meek was out in the streets actually doing it. In 2008 he was arrested, then convicted of drug dealing (and gun possession) and was sentenced to 11 – 23 months in prison. He was released early on a five-year parole agreement, which he violated 3 years later. After numerous other warnings and arrests, Meek Mill was sentenced to another 6 months in prison, followed by house arrest.
His house arrest finally ran out on June 2, 2016, and for now, Meek remains law abiding, but time will tell whether or not he will be tempted to return back to his roots.
#12 – Allen Iverson
Allen Iverson played 14 seasons in the NBA, excelling both as a shooting guard and as a point guard. Over the course of his career, Iverson won the All-Star game MVP award twice, was crowned NBA’s MVP, and played in the NBA All-Star game 11 of his 14 seasons. Regardless of your personal opinion of the man, it’s hard to deny his talent as a basketball player.
That said, Iverson had led a very rough life off the court. He grew up poor in Hampton, Virginia with his single mother. His father left him and his then-15-year-old mom, when he was still a baby. Many believe that it was the lack of a strong male role model in his childhood that sparked his rebellious behavior.
Iverson’s legal issues started back in the late ‘90s when he and a few friends were pulled over for speeding. Iverson was arrested for possession of marijuana and carrying a concealed weapon. After pleading no contest, Iverson was only sentenced to community service. Around that same time a lot of his closest friends were arrested and charged with dealing drugs out of Iverson’s Mercedes.
#11 – Pusha T
As you can tell from this list, a lot of rappers have sold drugs at one point or another before their careers took off. American hip-hop artist, Pusha T, continues to reinforce that stereotype. Before making it big in the hip-hop community, Pusha T openly admits that he used to deal drugs in order to get by.
If you’ve ever listed to any Pusha T songs, the fact that his roots lie in the streets shouldn’t come as a big surprise. He often raps about his struggles, tough upbringing, and selling drugs. One of his songs has a catchy line that claims that he “sold more dope than records,” and although that might be a slight hyperbole, Pusha isn’t shy when it comes to talking about his criminal past.
While his history and early years might be a bit questionable, Pusha T is on the come-up today. As of 2016, his net worth is estimated at a cool $15 million but is set to rise with the release of the highly anticipated King Push album said to drop sometime later this year.
#10 – Floyd Mayweather Sr.
Floyd Mayweather Sr, a former boxer, is the third athlete on our list with a history of dealing drugs. The senior Mayweather had a fairly impressive fighting career and did quite well in the welterweight division in the 1970s and 1980s. Obviously, the fighter thought that his career winnings weren’t enough, so he turned to a life in the drug trade.
It’s uncertain how much time Mayweather spent dealing drugs, but his operation began to crumble in the early ‘90s. By 1993 he was arrested for selling cocaine and was convicted of trafficking. Allegedly, Money Mayweather’s father was part of a smuggling ring, who as a group would move a lot of cocaine in laundry detergent boxes.
After his arrest, Mayweather was sentenced to a five-year stretch, leaving his son without a boxing coach. While he was in prison, his younger brother, Roger, took over the training regimen of Junior. This put a lot of stress of the relationship of the family as a whole, and although Sr. eventually started training Money Mayweather again, the two never fully reconciled.
#9 – Fat Joe
Joseph Cartagena, better known by his stage name ‘Fat Joe’ is a Bronx rapper that was heavily influenced by the Zulu Nation culture in his youth. His love for hip-hop began growing when his older brother, Angel, would bring home tapes of music played at those events. Aside from rap, there was a lot more that Fat Joe learned from his brother, for example, the life on the street.
At the same time, as he was getting interested in hip-hop, Fat Joe also got heavily involved in the drug trade. His involvement earned him his first nickname of Joey Crack. Some say that it was his fascination with the hip-hop culture that influenced him to sell cocaine (since a lot of other rappers were doing it).
Luckily, before he managed to get in too deep, Fat Joe decided to seek other revenue streams and began to pursue his true passion – music. After cleaning himself up, Joe began working on his demo tapes, eventually being approached by Relativity Records with a record deal. Joe accepted the offer, and the rest is history.
#8 – The Game
Jayceon Terrell Taylor (a.k.a The Game) is best known as a West Coast rapper. The Game rose to fame after being signed by Dr. Dre to Aftermath Records back in 2003. After a few mediocre mixtapes, The Game finally rose to fame with his debut album The Documentary. In less than a year after its release, the album was certified double platinum, with record sales of over 5 million copies worldwide.
The Game continued to strive in the music industry through the 2000s, but not without his fair share of legal troubles. The Game has a very impressive rap sheet (pun intended). From battery to weapons possession to gang affiliation to intentional infliction of emotional distress and everything in between, it’s fair to say that The Game doesn’t think too highly of the legal system.
The legal issues started way before he was a mainstream rapper, though. Graduating from Compton High School, The Game was enrolled in Washington State University on a basketball scholarship. His full ride didn’t last very long, as he eventually got kicked out of the school for possession of drugs. After the formal expulsion, The Game completely embraced the street life and began selling drugs and running with gangs.
#7 – Wu Tang Clan
Wu Tang Clan is a hip-hop group composed of ten rappers (one of which is now deceased) that managed to rock the world with their seven gold and platinum studio albums. Combined, the albums sold more than 40 million copies since the formation of the group in the early ‘90s. In fact, their debut album, Enter the Wu-Tang, is widely considered to be on the greatest albums in hip-hop’s history.
Despite being considered legitimate businessmen today, the group wasn’t always so law abiding. Aside from numerous insignificant run-ins with the law, the group was under an FBI investigation back in 2012. Secret FBI showed that the group was linked to carjackings, murders, drug dealing and money laundering.
Independent files of the group members are riddled with a history of violent crime and other serious transgressions which took place in the late 90s. A more serious allegation involved one of the WTC members being alleged as a suspect in an unsolved murdered. That FBI document was heavily redacted, making it unclear whether or not the allegation holds any merit. That said, the group continues to work together and put out great music to this day.
#6 – Lil’ Kim
Lil’ Kim (real name Kim Jones) found her way to the spotlight after being discovered by the Notorious B.I.G on the streets of Brooklyn. After working with Biggie, Lil’ Kim developed a voice of her own and gained notoriety for her explicit raps often highlighting female sexuality.
She raps about her many lovers, most notable of which was a drug lord known as Damion “World” Hardy. Her ex was recently sentenced to six consecutive life sentences for ordering numerous murders and trafficking drugs. Judging by the type of people Lil’ Kim associated herself with, it shouldn’t come as a huge surprise that the 4-foot 11-inch artist sold a fair bit of drugs herself.
Although she never served any prison time, Kim Jones says that she had to sell drugs for financial support. The death of Biggie also hit her hard, and she was forced to cope with that in her own (often illicit) way. Today, however, Lil’ Kim is a respectable businesswoman, artist, and actress with a modest net worth of $18 million.
#5 – Tim Allen
In a drug related article full of rappers, America’s favorite dad probably stands out the most. Believe it or not, Tim Allen was a convicted drug dealer before scoring his big break. Prior to his arrest, Allen worked at an advertising firm while at the same time trying to kickstart his stand-up comedy career. All of that came to a halt when he was caught with 650 grams of cocaine.
Allen was busted by drug-sniffing dogs at the Kalamazoo International Airport with nearly 1.5 pounds of cocaine – let that sink in for a second. Transporting this large of an amount over an international border can easily warrant a life sentence in the United States. Luckily, Tim managed to score a plea deal by exposing some bigger players in the business and had his sentence reduced to 3-7 years.
Due to good behavior, Allen was released from prison just 28 months after being admitted. Obviously, he managed to turn his life around, considering that he eventually became a world beloved superstar. From briefly becoming an A-list celebrity on the kid-friendly entertainment scene to cashing out with $1.25 million per episode in the final season of Home Improvement, Allen definitely made up for the time lost at the Federal Correctional Institution of Sandstone Minnesota.
#4 – Killer Mike
Michael Render, better known by his stage name Killer Mike made his hip-hop debut in 2000 when he featured on OutKast’s album Stankonia. He quickly gained the respect of the hip-hop community and started releasing his own music which did quite well on the Billboard Hot 100 list. Aside from music, Killer Mike has also starred in a number of films and even lent his voice to an Adult Swim cartoon back in 2006.
Although he might be worth a fair bit these days, Killer Mike didn’t always earn an honest living. In an exclusive VladTV interview, Killer Mike talked about his upbringing and the lessons that he learned from his father, who used to be a police officer. According to his track record, though – he didn’t learn much. Mike admits to selling large amounts of marijuana when he was in college, apparently to help pay his tuition.
As he became more popular, Mike also started to get more vocal on the War on Drugs. He became a loud proponent of ending the War on Drugs, claiming that it unfairly targets lower-class men, usually those of color. He and his father disagreed on a lot of things but stood on common ground when it came to racial discrimination.
#3 – O.T. Genasis
You probably remember O.T. Genasis from his entrance into the mainstream hip-hop scene back in 2014 with his bombastic anthem – “CoCo.” For those not in the know, CoCo was an over the top praise to dealing cocaine, with its most catchy line chanting “I’m in love with the CoCo” over and over again. The catchy song made the Long Beach rapper on overnight sensation, but O.T. has been quietly grinding for years.
Prior to CoCo blowing up, O.T. Genasis struggled to get in the spotlight. He caught his first break back in 2011 with his track, Jackie Chan, which caught the attention of 50 Cent who would eventually sign him to G-Unit records.
Before making it in the hip-hop community, O.T. Genasis had to resort to illicit means of making ends meet. While he just raps about CoCo now, he has confirmed that his lyrics also allude to his past, when used to sell cocaine to get by. In an interview with Hot 97 O.T. Genasis also admitted to using large amounts of the drug prior to the birth of his son, he claims to be completely clean now.
#2 – Young Jeezy
Jay Wayne Jenkins, or how you probably know him, Young Jeezy, got his rise to fame as a young rapper from Atlanta, Georgia. As for many rappers, Jeezy’s childhood was somewhat rough. Caught in the middle of both of his parents in a custody battle, Jeezy spent a lot of time traveling between family members, never really getting time to properly settle down. When asked about his childhood, Jeezy described it as “empty.”
It was his rough upbringing that likely contributed to the many run-ins he had with the law, most notable of which was for narcotics possession. In 1994 he spent nine months in a youth challenge academy boot camp, in an effort at rehabilitation.
In an interview with the Rolling Stone, Jeezy recalled dealing drugs. He says that he was selling crack cocaine on the streets of New York as young as 11. After his parents separated, his mother turned to alcohol and became emotionally unavailable, so Jeezy coped in his own way. His coping mechanism revolved around dealing drugs, and at the time, he was selling crack out of his grandmother’s house every morning before making his way to his middle school classes.
#1 – Busta Rhymes
Topping off our list is yet another American rapper, Trevor George Smith, Jr., better known by his stage name Busta Rhymes. Before becoming a platinum-selling hip-hop artist, Busta had to go through his fair share of trouble. He lived with his mom, who had to work long hours as a receptionist in order to provide for the family.
In an interview with Complex, Busta says that he got fed up with seeing his mom come home with swollen ankles, and decided to help out. That’s when the hip-hop artist started selling drugs to help provide for the family. Busta also admits to commits a slew of other crimes at that time, including assault and robbery.
Luckily, Busta managed to channel his energy into making music, which eventually paid off. Today he is worth more than $20 million and is still widely considered one of the best performers in the industry. Aside from music, Busta is now working alongside advocacy groups helping drive prison reform – particularly advocating against mandatory minimum sentencing laws.