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

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.

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.

12 Lauryn Hill

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.

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.

9 Ol' Dirty Bastard

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.

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.

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.

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.

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.

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.

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.

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!

Looking for an AD FREE EXPERIENCE on TheRichest?

Get Your Free Access Now!

More in Entertainment

15 Mugshots Of Legendary Rappers Who Did Jail Time