17 Old School Rappers Over 40 Still Making Music

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We list some of the best Old school rappers over 40 still making music. Staying relevant is the most challenging part of being a rapper, especially when the genre has a low barrier to entry. When the fans love you, it’s all about living the high life. When the new school rappers comes along, veteran or old school rappers seem to fade into the background. However, some of the old school rappers have been able to stay relevant for a long period of time. They’ve consistently put out lots of music that fans, new and old, have come to like.

1. Jay-Z

Jay-Z is not only one of the most successful rappers but also a successful entrepreneur, who owns an entertainment company named ‘Roc Nation’. The New York rapper is the embodiment of the rags-to-riches rap dream, largely due to his unsurpassed lyrical talent, incredible dedication, and industry smarts. Growing up, he explored his rap skills when he briefly attended Eli Whitney High School with fellow rappers Notorious B.I.G and Busta Rhymes. Later on, he co-founded the record label Roc-A-Fella Records in 1995 and released his debut studio album Reasonable Doubt in 1996. The album was released to widespread critical success, and solidified his standing in the music industry. After several multi-platinum albums, Jay-Z is now one of the world’s best-selling music artists, with over 140 million records sold, and has won multiple Grammy Awards.

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2. EMINEM

Eminem is known as one of the most-controversial and best-selling artists of the early 21st century. He dropped out of school in the ninth grade and worked odd jobs until finally making it as a rapper upon the release of The Slim Shady LP in early 1999. The album went multi-platinum, garnering Eminem two Grammy Awards and four MTV Video Music Awards. One of the best-selling white rappers of all time, Eminem has won numerous awards, including at least 15 Grammy Awards.

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3. Snoop Dogg

Snoop Dogg is a veteran in the game and the very definition of a real OG, synonymous not only with West Coast hip-hop. During his youth that was after graduating from high school, Snoop Dogg was frequently in trouble with drugs and law, in and out of jail for nearly three years. Released from jail he embarked on making homemade rap tapes with his friend Warren G, who was a stepbrother of Dr. Dre of N.W.A. After all, Dr. Dre asked him for collaborations, first on the theme song of the film “Deep Cover,” and then on Dr. Dre’s debut solo album “The Chronic.” Since then his career that has spanned gangsta rap to R&B. Snoop Dogg is regarded as one of the best old school rappers out there.

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4. Kanye West

Kanye West has been responsible for cultural movements and progressions within mainstream hip hop and popular music at large. In the span of three short years, Kanye West went from hip-hop beatmaker to worldwide hitmaker, as his stellar production work for Jay-Z led to a major-label recording contract and, ultimately, a wildly successful solo career. Each of his albums has been massive critical and commercial successes, including his collaboration album with JAY-Z, Watch the Throne. West has won an astounding 21 Grammy’s, tied with JAY-Z as the most decorated hip-hop artist in Grammy history.

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5. Dr. Dre

Dr. Dre‘s influence on hip-hop is vast and far-reaching. He played a major role in the G-Funk movement of the late 80s/early 90s. The West Coast music producer and rapper immersed himself in the early Los Angeles hip-hop scene and in 1984 formed the World Class Wrecking Cru, a romance-themed, techno-style group whose song “Surgery” was a local hit. In 1986 Dr. Dre teamed up with Eazy-E , Ice Cube, MC Ren and DJ Yella) to form the seminal rap group Niggaz Wit Attitude, or N.W.A.. Dre’s production talents received widespread exposure on N.W.A.’s second album Straight Outta Compton (1988), which sold over 500,000 copies in six weeks with virtually no radio or video play. He also helped propel West Coast hip-hop to new heights with his masterwork, The Chronic.

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6. Nas

The son of jazz musician Olu Dara, Nas was raised in the infamous Queensbridge housing projects in Queensbridge, New York. Regarded as one of the best New York rappers of all time, Nas released his debut album called Illmatic which rose to No. 12 on Billboard Hot 200 and garnered positive review from music lovers. With high expectations, Illmatic proved to be just as astounding as it had been billed. It sold very well, spawned multiple hits, and earned unanimous acclaim, followed soon after by classic status.

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7. Diddy

Diddy also known as Puff Daddy, successfully carved a niche for himself, and went on to become one of the most popular artists in the music industry. He’s a Grammy Award-winning hip-hop mogul whose debut album, No Way Out, went 7x platinum, and whose song, “I’ll Be Missing You,” became a No. 1 Billboard hit. Forbes magazine also ranked him as one of the richest rappers hip hop.

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8. Missy Elliott

Missy Elliott made a mark on the male-dominated hip-hop world with her talents for writing, rapping, singing, and music production. Involved in her local church and choir, Elliott in 1991 started Fayze, an all-female R&B group whose producer was neighborhood friend Timothy “Timbaland” Mosley. In 1996, Elliott worked with SWV, 702, Total, Destiny’s Child, and Aaliyah. Later that year she became a featured vocalist rapping on Sean “Puffy” Combs Bad Boy Records’ remixes. Her big breakthrough came when “The Rain”, a single from her debut album, Supa Dupa Fly (1997), became certified platinum.

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9. Juicy J

Juicy J is a founding member of the Southern hip hop group Three 6 Mafia, established in 1991, and also the younger brother of rapper Project Pat. Together with production partner DJ Paul, Juicy J played an important role in the South’s rise to prominence within the once East and West Coast dominated rap industry. In 2002, he released his solo debut album Chronicles of the Juice Man, in between Three 6 Mafia projects. Juicy J also received a Grammy Award nomination for his feature on the Katy Perry single “Dark Horse”, which peaked at number one in the US.

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10. Fabolous

Fabolous began his career in 1998 when he rapped live on a Hot 97 show hosted by DJ Clue. His debut album, Ghetto Fabolous, was released in 2001 and featured the hit singles “Can’t Deny It” and “Young’n (Holla Black)”, which led him to prominence. His second album, 2003’s Street Dreams, was supported by two Top 10 singles “Can’t Let You Go” and “Into You”. The album was also a success, selling over a million copies and peaking at the third position on the US Billboard 200. Fabolous is recognized as one of the best old school rappers of his generation.

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11. Jeezy

At the age of 24, Jeezy released an indie album called “Thuggin’ Under Influence” with Lil J as his moniker. The following years, he spawned more mixtapes that impressively sold averagely around 100,000 copies within a year. Soon Bad Boy Records signed him in 2004 as one part of rap group Boyz N Da Hood. With the boys, he released a self-titled album in 2005 that peaked at No. 5 on Billboard Hot 200 chart. Despite the success, he left the group and the label to go under Def Jam as a solo artist. He released a debut solo album Let’s Get It: Thug Motivation 101 under the new label. It went on platinum at the end of 2005 and propelled him as a capable solo artist. Jeezy was unconcerned about mainstream response to his music, considering the poor people on the streets to be his true audience. He consistently refused to become commercial or to cross over to other genres.

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12. Jadakiss

Jadakiss is a member of the music group The LOX, and one of the three founders of the imprint D-Block Records. The group, especially Jadakiss, developed a close relationship with The Notorious B.I.G., during which time Jadakiss was taken under Biggie’s wing. After releasing two albums as a member of The LOX, Jadakiss released his debut solo album, Kiss tha Game Goodbye, in 2001 to mixed reviews from critics. His second album, Kiss of Death, was released in 2004 and featured his most successful song to date, “Why?”, which charted at No. 11 on the Hot 100.

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13. E-40

In the beginning, E-40 was an underground artist and debuted his 1995 solo album In a Major Way. He then started working with more mainstream rappers outside the Bay Area in 1998. With his only “Tell Me When to Go”, produced by Lil Jon, in 2006, he started to gain recognition. However, E-40 is also an old school veteran who has done collabos with rap icons such as Tupac Shakur, Too $hort, Lil’ Jon, C-BO, Snoop Dogg, Spice 1, Richie Rich, Mac Dre, Mac Mall, The Luniz, The Outlawz, and many more.

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14. Camron

Camron is the de facto leader of East Coast hip hop groups The Diplomats and U.N. After earning airplay for his own single, “Pull It,” in May of 1998, Cam’ron emerged again for cuts on two movie soundtracks. The first was a track with Lil Cease for How to Be a Player entitled “Casanova,” followed by “3-5-7,” featuring rap star DMX, for the film Woo. The latter song provided Cam’ron with his first entry into the Billboard R&B chart in June of 1998. Subsequently, in July, Cam’ron returned with the single “Horse and Carriage,” featuring Mase. With this effort, Cam’ron rose into the R&B top ten and just missed entering the Billboard Top 40.  Cam’ron continued to rap, and he released his solo debut album, Confessions of Fire, in 1998. He has since released 2000’s S.D.E, 2002’s Come Home With Me, 2004’s Purple Haze, 2006’s Killa Season and 2009’s Crime Pays.

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15. Killer Mike

Killer Mike was first heard on “Snappin’ and Trappin'”, a song from OutKast’s album Stankonia (2000). He later appeared on the Grammy-winning song “The Whole World”, a single from OutKast’s greatest hits album Big Boi and Dre Present…OutKast. In December 2008, Mike signed to T.I.’s Grand Hustle Records. In 2012, he released R.A.P. Music, produced by rapper-producer El-P. In 2013, the two formed a duo called Run the Jewels. The two signed to Fool’s Gold Records and released Run the Jewels in June of that year. He was named to NME’s “The Ten People Who Defined 2020” list for his powerful lyrics and activism, his album, RTJ4, made Variety’s “Best Albums of 2020” list alongside Taylor Swift, The Weeknd, and he was named as the recipient of 2020’s Billboard Change Maker Award.

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16. Jim Jones

Bronx born and Harlem raised rapper Jim Jones is a founding member of the hip hop collective The Diplomats, who are also known as Dipset. He hit the scene alongside Cam’ron, Freekey Zekey and Juelz Santana in 1997. The group made their first commercial appearance on Cam’ron’s album, S.D.E., which was released in 2000. In 2004, Jim Jones released his first solo album On My Way to Church. The release of his second album, Harlem: Diary of a Summer in 2005, coincided with Jones landing an executive position in A&R at E1 Music. A year later he was on his third album which spawned his biggest single to date “We Fly High”.

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17. Jay Electronica

Jay Electronica first received widespread attention after the release of his debut mixtape, Act I: Eternal Sunshine (The Pledge), in 2007, and was signed to Jay-Z’s record label Roc Nation in 2010. His debut studio album, A Written Testimony was released in 2020 and followed up by Act II: The Patents of Nobility (The Turn). 

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