15 Mugshots Of Legendary Rappers Who Did Jail Time

Rap music has diversified tremendously over the last decade. What began as a street-centric-gangster genre of music, has evolved into a more mainstream art form.

Many of the legendary rappers that we have come to know have gone through incredible circumstances to find themselves as legends of the game. Some have had to endure extreme poverty and did whatever it took to accomplish their dreams, and for some it was simply a way to escape the harsh circumstances of their lives. We often find a way to relate to these people because their stories are so real. We can relate to their struggles, trials and tribulations. Anybody can pick up a microphone and start rapping, but very few people have the skillset and self-awareness needed to properly articulate their feelings and emotions and translate them into rhymes. The realer the experiences, the deeper the rhymes and the more connected we become to the artist. It’s really that simple. Because more often than not, the more an artist speaks truthfully, the more the audience will relate to their experiences.

Sometimes that truth is just too real and is a result of self-reflection after serious real life consequences. And although these rappers find themselves at the top pages of the hip hop history books, their offences will forever remain on their criminal records. Here are 15 Mugshots of Legendary Rappers Who Did Jail Time.


15 DMX

DMX grew up in Yonkers, New York, and went through a very abusive childhood. His venture into hip hop began at 21 years old as a beatboxer, and he eventually evolved into a rapper. Although having sold 54 million albums worldwide throughout his career, his excessive spending over the years has forced him into debt. This explains his most recent incarceration in 2015 for outstanding child support charges. He was sentenced to 6 months in jail for failing to pay $400,000 to his ex-wife and their four kids.

14 Flavor Flav

Flavor Flav’s claim to fame came in 1986 when his rap group, Public Enemy, was signed to Def Jam Records. His musical contributions to the group were minimal, as his role was primarily that of a hype man. He was known for being extremely eccentric, getting fans excited during live concerts, and wearing bizarre clothing like big hats and oversized clocks as necklaces. Many hip hop artists have payed homage to Flavor Flav over the years in their songs because of his powerful influence on hip hop culture.

Flavor Flav has had his fair share of legal issues. He served 30 days in jail in 1991 for assaulting his girlfriend. He was sentenced to 90 days in jail in 1993 for shooting his neighbor. In 2002, Flav spent nine weeks in jail for driving with a suspended license and unpaid parking tickets.

13 Lil Wayne

Lil Wayne was signed to Cash Money Records at 9 years old. Over the span of his career, he has sold over 100 million records worldwide and is one of the best-selling artists of all time. He propelled himself to superstardom in 2006, when he began to release back to back critically acclaimed mixtapes. He was also featured on over 200 songs between 2006 and 2009, something no other rapper has ever come close to matching.

Having been arrested multiple times throughout his career for gun and drug possession, Lil Wayne was convicted and served a one-year sentence on Riker Island in 2010.

12 Lauryn Hill

Lauryn Hill’s debut solo album, The Miseducation of Lauryn Hill, was a critical and commercial success. Her ability to blend singing and rapping together, and also her production involvement on the album, helped establish her as a legend of hip hop. Like many of her counterparts, Lauryn Hill’s poor management of finances landed her in jail for 3 months for 1.8 million dollars of tax evasion.

11 Snoop Dogg

Snoop Dogg was heavily featured on Dr. Dre’s solo albums, The Chronic and 2001. His affiliation with Dr. Dre, unique style and flow, and his laid back and cool demeanor helped him gain a huge, loyal fanbase very early on in his career. His debut album Doggystyle, has sold over 4 million copies, and his music catalogue has gone on to sell over 30 million copies worldwide.

Snoop Dogg was arrested multiple times starting from a very early age. Most of his arrests were drug related charges. He was charged as being an accomplice to a murder in 1993, but was found not guilty due to the jury being deadlocked.

10 Max B

Max B entered the music industry through his affiliation with Juelz Santana, Jim Jones and Cam’ron from the Dipset group. Although he never broke into mainstream hip hop, his Million Dollar Baby mixtape and Public Domain solo album generated a lot of street buzz. Max B then entered into the mainstream spotlight for the wrong reasons in 2009, when he was charged with murder, kidnapping and armed robbery, and sentenced to 75 years in prison.

You can hear Max B on Kanye West’s The Life of Pablo album. The interlude track, Silver Surfer Intermission, is a conversation between Kanye West and Max B while he is incarcerated.

9 Ol' Dirty Bastard

A true hip hop legend, O.D.B was a founding member of the Wu Tang Clan. ODB became as notorious for his erratic behavior as his hit singles, "Brooklyn Zoo" and "Shimmy Shimmy Ya." He will forever be remembered for his unique free-flowing rap style that mixed singing and warbling together. ODB served time for multiple assault charges, theft and drug charges, throughout his life until his death in 2004 of a drug overdose.


8 Sean Combs

One of hip hop's greatest moguls of all time, Sean Combs has amassed an incredible fortune thanks in part to his great business sense and ability to monetize on the hip hop culture. Sean Combs began his career in the music industry working as an intern at New York’s Uptown Records. In 1993, he formed his own record label, signed Notorious BIG, and the rest is history.

Despite having built an empire that includes a clothing line, TV network, record label and merchandise, Diddy has had his fair share of legal troubles. He was most recently arrested in June 2015, for assaulting his son’s football coach after witnessing the coach yelling at his son. He reportedly also swung a kettlebell at the coach and nearly seriously injured him.

7 Lil Kim

Lil Kim was a pioneer for all women in the hip hop industry. She carved her way to mainstream success in what was, and still is, a predominantly male dominated genre. Her music career took off in 1995 when she performed a freestyle rap for Notorious B.I.G. Impressed by her skills, he recruited her into his Junior M.A.F.I.A rap group. Her success in the music industry opened doors for countless female rappers after her, most notably Nicki Minaj, who is an international superstar today.

Lil Kim was sentenced to one year in prison in 2005, for lying to a Federal grand jury to protect her friends that were involved in a shootout outside a Miami radio station.

6 50 Cent

With Eminem and Dr. Dre by his side, 50 Cent rose to international fame with his debut album Get Rich or Die Trying. He began selling drugs at 12 years old and although having left the gangster life to pursue a career in music, he was shot nine times in 2000.

50 Cent has been arrested multiple times throughout his life, the first time being in 1994 at the age of 19, for selling cocaine to an undercover police officer.

5 T.I.

An Atlanta legend, T.I is best known as the artist that popularized trap music. His albums were a blend of both real, street centric music and mainstream hits. He has also release several highly successful singles throughout his career, featuring artists like Justin Timberlake, Rihanna and Lil Wayne.

No stranger to legal problems, T.I served two terms in county jail for both probation violations and weapons charges.

4 Vanilla Ice

A legendary rapper for literally all the wrong reasons, Vanilla Ice gained international fame for his hit single Ice Ice Baby, in 1990. It was the first hip hop single to ever top the Billboard charts. After a few years of riding the wave from the fame of his single, Vanilla Ice’s career quickly spiraled downwards as he was never able to top the success of that record. He began heavily using cocaine, ecstasy and heroin, and slowly disappeared off the radar.

He was arrested multiple times in his life, most notably in 2008 for hitting and kicking his wife.

3 Tupac Shakur

Tupac Shakur is consistently ranked as one of the greatest and most influential rappers of all time. He has sold over 75 million records worldwide before his tragic death in 1996 from a drive-by shooting incident. Tupac mastered every element and aspect of rapping. He was widely viewed as a poet. His lyrical content and song structure were never before seen in his genre of music. His influence has been noted by nearly every rapper that came after him.

He had many legal issues throughout his entire life, the most serious of which was an incident in which he was convicted of first degree sexual abuse and sentenced to 1-4 years in prison. He was released from prison after serving nine months. The CEO of Death Row Records posted a 1.4 million dollar bail for him, in exchange for three albums he would have to record under the label.

2 Eminem

Eminem is one of the best selling artists in the world, with 172 million album sales since he started his career. He is considered one of the greatest hip hop artists of all time and was widely considered to be a cultural icon during the prime of his career. He has won countless awards and many of his albums have been critically acclaimed. The Marshall Mathers LP was the fastest selling solo album in US history and was ranked one of the greatest albums of all time by Time, Rolling Stone and XXL magazine.

His controversial lyrics and lifestyle have caught up to him multiple times throughout his career. He has been arrested countless times for reasons stemming from assault to gun charges.

1 Jay-Z

From being a drug dealer in the Marcy Projects to building an empire, Jay-Z’s ascension into the history books of rap music is nothing short of remarkable. In 2012, Jay-Z beat Elvis in the record books for having the most number one albums by a solo artist on the Billboard 200. His combination of both artistry and business acumen ensured that he always remained in an ownership position of any situation he got himself into. From helping build a record label, clothing line, sports management company and entertainment company, Jay-Z always makes sure he gets a slice of the pie.

Although having never gotten caught by law enforcement from his previous life as a drug dealer, Jay-Z did get arrested in 1999 for stabbing Lance Riviera. Riviera allegedly was responsible for an early leak of Jay-Z’s Vol 3. album. When Jay confronted Riviera at a nightclub about the situation, he lost his temper and reportedly stabbed Riviera. He ended up pleading guilty to a misdemeanor and accepted a three-year probation sentence. He also vowed to himself that it would be the last time he puts himself in a compromising situation, and it was; he has never gotten arrested since.


Give TheRichest a Thumbs up!

More in Entertainment