37 Best 90s Hip Hop Rappers

The nineties are perhaps the best era of hip hop, and many 90s rappers still command respect within the industry as ideals to look up to. Here are some of the best hip hop rappers of the 90s.

37. LL Cool J

LL Cool J started music at a young age. Dealing with abuse and the near-murder of his mother and grandfather by his dad, plus abuse from his mother’s ex-boyfriend, he started rapping at age 10 after being influenced by an older group, The Treacherous Three.

One of his earliest releases helped establish Def Jam as a label, alongside some work from the Beastie Boys. Def Jam is one of the largest and most influential labels in rap and hip hop, supporting many other artists on this list, so establishing it this well may have helped pave the way for rap’s rise throughout the 90s.

LL moved on to release four albums throughout the 90s and has remained active since, including some work in film and television.

Album Recommendation: LL Cool J has many excellent releases, but consider starting with Radio, which is one of the first genuinely successful hip hop albums ever released.

36. Redman

Best known for hits like Funkorama in 1995, Redman was consistent and entertaining throughout the 1990s. Bouncing from threatening to comedy and showing off a consistent party vibe, Redman opened in 1990 and exploded outward within just a few years.

Rap has a long history with provocative and unexpected lyrics, and few rappers have managed unpredictable energy with the same degree of panache as Redman. It’s hard to overstate the value of an excellent body of work, too. Plenty of rappers release just one good song or album and then disappear, so consistency is what separates the skilled from the masters.

Album Recommendation: There’s no better place to start than Whut? Thee Album, Redman’s debut release. Although it only peaked at forty-ninth on the Billboard 200, The Source magazine was impressed enough to name him Rap Artist of the Year for his impressive technical performance.

35. Flavor Flav

Best known for his work with the rap group Public Enemy, Flavor Flav is a Grammy-winning star and cousin of several members of the Wu-Tang Clan. Flav famously wears a clock around his neck in public appearances, which he says helps remind him of the importance of time and how it keeps on going.

Unlike some other rappers, Flav has little solo work to his name, with only a single solo album that came out in 2006. He was overlooked in the initial signing of Public Enemy to Def Jam Records, but his partner Chuck D insisted on them signing together, and they went on to rapid fame.

Part of the reason for their success was the balance within the act. Chuck usually had a serious and political style, which Flav balanced with comedy to mainstream effect. The two have released more than a dozen studio albums and many additional works, remaining active within the industry.

Although not a chart-topping sensation like some other rappers, he remains well-liked within the industry, and the classic nature of some earlier albums ensures lingering popularity. Unusually, Public Enemy’s work tends to do better in the United Kingdom, so they’re a little more well-known there.

Album Recommendation: While he has a solo album, almost all of Flavor Flav’s work is part of Public Enemy. Of these, the ideal place to start is It Takes a Nation of Millions to Hold Us Back, their first platinum-certified release.

34. Eve

Hip-hop and rap trend towards male performers, but there are some outstanding female entertainers in the industry. Eve Cooper barely edges into the best rappers of the 90s with her debut album coming out in September 1999, but a technical qualification for this list still counts.

Not many singers can boast of hitting #1 on the Billboard 200 with their debut, and at the time, she was only the third female rapper to claim that achievement. Since then, Eve has diversified into everything from television presentation and acting to managing clothing lines, plus collaborations with modern fan-favorite personalities like Doja Cat.

Unfortunately, Eve doesn’t have as many albums as some other rappers, but she does have quite a few singles and collaborations that have come out over the years. We can’t count these towards her score because most of them came out past the 90s, but it’s hard to overstate Eve’s position or performance as one of the leading women in hip-hop.

Album Recommendation: As with many artists, Eve’s debut album is an excellent showcase of her skills. Let There Be Eve…Ruff Ryders’ First Lady is a twice-over platinum release, and she wrote every track on it.

33. Juvenile

Born Terius Gray but determined to live up to his stage name, Juvenile came onto the scene with his debut album Being Myself, released in 1995 through Warlock Records. Soon after, he signed with Cash Money Records and joined several other artists to form the Hot Boys group.

However, it wasn’t until 1998 that he hit national recognition. His album that year, 400 Degreez, had the benefit of joint distribution through Universal Records and access to a much wider audience. It remains his best-selling album to date.

Juvenile has remained active in music since his debut, releasing a mix of studio and collaboration albums throughout the mid-90s and on through the 2000s and 2010s. Although never selling quite well enough to qualify as a superstar, Juvenile has worked with some of the most famous names in rap and remains worth listening to.

Album Recommendation: Listening to his earlier works isn’t bad, but Juvenile hit his stride with 400 Degreez, a 4x Platinum release. That’s higher than almost any work from anyone else on this list, a clear showcase of his skills.

32. MCA

Best known for his work with the Beastie Boys, and one of the few non-black rappers to achieve significant fame, Adam Yauch was a founding member of his band brought in when a previous band split apart.

As a hip hop trio, the Beastie Boys released their first album through Def Jam Records when he was just 22, and he further supported the group by serving as director for most of their music videos. MCA died of cancer in 2012, which led to the Beastie Boys ceasing all operations as a band.

MCA’s work is heavily grounded in his band, appearing in nine albums with them. Unlike many other artists on this list, he doesn’t have solo studio albums, but the multi-platinum nature of most of the band’s albums showcases his skill.

Album Recommendation: It’s impossible to separate his work from the other Beastie Boys, so start with Licensed to Ill, which is one of a bare handful of hip hop albums to reach Diamond certification.

31. Ad-Rock

One of MCA’s partners in the Beastie Boys, Adam Horovitz came on to replace John Berry when the latter left the group. As part of the group, Ad-Rock was a part of creating the band’s many award-winning albums. He was also integral in changing their sound from hardcore punk to hip-hop, earning all of the Beastie Boys a place on this list.

Outside of his work with the Beastie Boys, Ad-Rock also has two albums with the group BS 2000, making him a little more spread out than his partners. Beyond that, he has some roles in film, but even more notoriety as a remixer helping produce tracks for other singers.

With four albums in the 90s and plenty of success in the years since Ad-Rock remains one of the most notable 90s rappers.

Album Recommendation: Just like the other Beastie Boys, it’s best to start with their album Licensed to Ill, which is one of the top releases of all time in hip hop.

30. Masta Killa

One of the lesser-known members of the Wu-Tang Clan, Masta Killa is relatively quiet and the last member to join the group. He also had less experience at the time of the debut album’s release, which is why he had few verses on it.

Although he didn’t release a solo album until 2004, he worked on many of the group’s classic projects. His raps also stand out for being laid-back and relaxed, a noticeable departure from the aggressive styles of most other members.

To date, Masta Killa has four studio albums, but a long slate of guest appearances. The general opinion is that he produces quality work in a rarer style, which serves as an excellent balance for songs that need it. While he’s not as prolific as some, Masta Killa deserves his place on this list thanks to his technical expertise.

Album Recommendation: Although he only had a small part in Da Mystery of Chessboxin in Enter the Wu-Tang (36 Chambers), hearing his lyrics alongside those of other members is a great way to see his early skill and provides a point of comparison for his work in later solo projects.

29. Eazy-E

Born in 1964, making him a little older than most other rappers of the 90s, Eazy-E was a prominent supporter of West Coast rap. This was most obvious in his participation in Ruthless Records, where he led the group N.W.A and in many ways helped popularize the gangsta rap genre.

The studio’s debut album, Straight Outta Compton, remains one of the most popular rap albums ever, and they released two more albums before the group split. Fellow members Ice Cube and Dr. Dre would go on for longer solo careers, but despite releasing two EPs, Eazy-E ultimately focused more on producing and activities behind the scenes.

Eazy-E died in 1995 from the onset of complications from AIDS, with most of his releases coming out in the late 80s and early 90s. N.W.A was hugely influential throughout the 90s, and all of his albums and EPs charted comfortably well on the Billboard 200.

Album Recommendation: Although he has independent albums, Eazy-E led the work on Straight Outta Compton, which remains a pivotal release in hip hop. That’s the place to start if you want to hear his work.

28. Cappadonna

Although originally slated to join the Wu-Tang Clan at its inception, especially with credentials from mentoring fellow member U-God, Darryl Hill’s time in prison stopped him from joining them properly, and he had only sporadic contributions. This has since been remedied, however, as he officially joined the group with the release of 8 Diagrams in 2007.

While he didn’t release a studio album until 1998, Cappadonna has been quite prolific since then, typically releasing an album every year or two and collaborating on other projects. He also features on several dozen tracks from other artists, lending his expertise to their songs.

As you might expect from someone who has served as a mentor to a member of one of rap’s all-time most popular groups, Cappadonna has a depth of knowledge of the styles and fundamental elements of music that sticks out even on this list of outstanding hip hop rappers. He’s a great choice to listen to if you’re looking for skill and complexity in music.

Album Recommendation: Cappadonna features extensively in The W, the third studio album of the Wu-Tang Clan, which has broadly performed better than many of his solo works. He’s mixed in with others, but it’s still an outstanding representation of his skill and work.

27. Busta Rhymes

Trevor George Smith Jr., better known to most as Busta Rhymes, is one of the most innovative 90s rappers. After releasing a debut album in 1996, he quickly started working on his next projects and released several more albums and hit singles in short order.

Although already capable with music, what sets Busta Rhymes apart from others is his impressive use of visuals in many music videos and performances. Dipping into video production isn’t rare among hip hop artists, but few have taken it this far.

Since his debut, Busta Rhymes has received more than 10 Grammy nominations, though he has yet to win an award for his work. Whether he eventually gets one or not, it’s worth watching his videos (and not just listening) to see why we rate him so highly.

Album Recommendation: Busta Rhymes has multiple platinum record releases, but his second album When Disaster Strikes… is a little better than his first, and a better place to start unless you want to hear his works chronologically.

26. Mike D

Part of the Beastie Boys rap group, Michael Diamond is one of the few non-black hip hop artists to achieve real fame and status before Eminem entered the scene. The whole group also predates most of the rappers from the 90s, having launched in 1981 after replacing some members from a previous band.

However, with a catalog of hits from the 80s powering them, the Beastie Boys were able to launch strong into the 90s. Check Your Head, an album released in 1992, was eventually certified double platinum, while Ill Communication debuted at #1 on the Billboard 200.

Most of his music stands out from more traditional hip hop thanks to the inclusion of many different elements into their music, including punk, jazz, and even Latin influences. Many top artists cite the entire band as an influence, though since the band stopped production after the death of Adam Yauch, he hasn’t made nearly as much music.

Album Recommendation: Like the other Beastie Boys, it’s best to start with their debut album, Licensed to Ill. It’s a pivotal release in rap and worth every listener’s time.

25. Snoop Dogg

Is there anyone who hasn’t heard of Snoop Dogg? Born Calvin Broadus Jr., he launched to fame as part of Dr. Dre’s debut solo singer and has catapulted into stardom where he’s remained ever since.

Snoop Dogg released his debut solo album Doggystyle in 1993, which was certified quadruple-platinum in 1994. He followed it up with Tha Doggfather, Da Game Is to Be Sold, Not to Be Told, and No Limit Top Dogg before the 90s were done, certifying him as one of the more prolific artists of the era.

Snoop has a prolific career in entertainment outside of music, appearing on television shows like King of the Hill and Robot Chicken, in various films, and even a wine brand. He also did some television work with Martha Stewart, which was an unexpected decision for many.

Snoop Dogg is particularly famous for a smooth, melodic delivery that uses effective yet simple terminology. He’s also known for his freestyle techniques, separating him from rappers who write and rehearse every syllable.

Album Recommendation: Snoop Dogg’s Doggystyle album is one of the most successful releases in the industry, with its distinctive G-Funk subgenre going mainstream and pushing the entire West Coast scene forward after its release.

24. U-God

Although he joined the Wu-Tang Clan early on, Lamont Hawkins was incarcerated and unable to contribute much to the debut album’s release. However, he quickly grew on fans through participation in other group tracks and featured heavily in the group’s second album.

U-God has released independent works slowly, starting with a studio album in 1999 and further releases every few years after. He’s also participated extensively as a guest in songs, particularly those of other Clan members.

U-God spent time learning under Cappadonna (another Wu-Tang Clan member), where he studied both rap and beatboxing. These remain present in his current works, and while he hasn’t had the individual success of some others, U-God remains popular with listeners and critics alike.

Album Recommendation: U-God’s work with the Wu-Tang Clan is more notable than his discography. He did particularly well with Wu-Tang Forever, which is a solid place for any listener to start.

23. Left Eye

Better known by some through her birth name Lisa Lopes, Left Eye was a rapper most famous for her time in the group TLC. Aside from being their main rapper, she also did much of the co-writing through the group and earned four Grammy Awards through it.

However, though she performed well in TLC, Left Eye noted during the release of their third album, FanMail, that she was mainly rapping and she couldn’t provide quite as much creative input as she wanted. To address that, she launched a solo career than ran from 1998 until 2002.

Unfortunately, Left Eye died in a car accident in early 2002 while filming a documentary in Honduras. She was the only one killed in the accident, which was recorded on video thanks to her current project.

As expected with any artist who dies so young, Left Eye’s actual discography is relatively short, though Mass Appeal Entertainment and eOne eventually released a collection of unreleased songs, remixes, and some new productions in a 2009 album.

Album Recommendation: Left Eye’s discography is so short that you can honestly start anywhere, but the posthumous release of Eye Legacy is her primary work available in the United States.

22. Lil’ Kim

Born in 1974 as Kimberly Jones, Lil’ Kim practiced freestyle rap in her early life before joining The Notorious B.I.G. and participating in the debut album Conspiracy, which generated two Top 20 singles.

However, her debut studio album Hard Core was what catapulted her to fame, becoming the strongest release for a female rap album at the time. It has since sold more than six million copies, part of fifteen million total album sales and more than 30 million single sales.

Although she didn’t release any new studio albums until 2000, she has since become an icon and inspiration for many in the industry, with numerous other women in hip hop crediting her as a major influence.

Today, her influence on the industry makes her worth listening to even if you’re only interested in the history of rap. Despite her fame, however, Lil’ Kim doesn’t have many studio releases. After releasing The Naked Truth in 2005, she didn’t have any other albums until releasing 9 (that’s the album’s name, not a number of albums) in 2019.

Album Recommendation: Lil’ Kim’s debut album, Hard Core, slightly outpaces her second release in the US and serves as a good gateway for her distinctive style.

21. 50 Cent

Known for lyrical brevity, 50 Cent is one of the all-time greatest influences on rap, a detail kicked into high gear when he was nearly killed in a shooting in 2000. Unlike some others, however, he survived the shooting and fully recovered about five months later.

Although he wouldn’t release an independent album until the 2000s, 50 Cent still qualifies as a 90s rapper thanks to his work with the group Onyx, especially on their 1998 album Shut ‘Em Down, where he appeared in the song React.

After recovering from the shooting, 50 Cent released a CD and got attention from Eminem, who then introduced him to Dr. Dre, and 50 Cent soon released his debut album at #1 on the Billboard 200.

Today, 50 Cent is actively involved in numerous business ventures, supporting everything from television and movies to books, video games, and real estate. His discography is relatively short, with five studio albums, but it was broadly successful enough to kick-start his later ventures.

Musically, he is especially involved with G-Unit Records, a label operating under Universal Music. G-Unit has sponsored numerous acts over the years, though 50 Cent’s works have been the label’s main success.

Album Recommendation: 50 Cent’s debut album Get Rich or Die Tryin’ isn’t quite Diamond-certified, but it’s close and will probably get there within a few more years. It’s also a rare title that’s hit multi-platinum in many different territories, marking it as an outstanding example of his work.

20. Method Man

A frequent collaborator with Redman, Clifford Smith Jr. is an all-star rapper and member of the legendary Wu-Tang Clan. He was one of two members to get a solo on the group’s first album and soon released a solo album under Def Jam Recordings.

Contrary to what his stage name implies, Method Man often tries out different styles for music, including some that lean towards funky beats and comedy instead of the speed and aggression of some others.

Since his debut, Method Man has been broadly prolific, releasing a series of studio and collaboration albums. He also has a moderate acting career, appearing in numerous movies and television shows. He has enough collaborations that it can be hard to separate him from group work, but he’s certainly worth a listen if you enjoy rap at all.

Album Recommendation: Although his independent works are excellent by themselves, the song Method Man from Enter the Wu-Tang (36 Chambers) is in many ways a much more personal introduction to his work.

19. Inspectah Deck

Inspectah Deck is one of the more unusual members of the Wu-Tang Clan. Unlike some of its more boisterous members, he typically maintains a relaxed and quiet attitude. Method Man noted that he has a sharp wit, however, and tends to see right through nonsense.

Although not a founding member of the group, Deck was the second-most-featured member of its debut album and provided some of the most iconic lyrics from it. From there, he also participated in many of the members’ other projects, further showcasing his lyric-writing skills.

Deck released a studio album in 1999, qualifying him for this list, and then several more throughout the years. Deck has also spent most of the 2010s working with Czarface (not to be confused with Scarface, the rapper), with whom he has nine albums.

Overall, despite his skill and surprisingly high number of works, Deck’s biggest contributions are often in his writing and support for other rappers. Lyrics have always been the heart of rap, and it’s those who excel here that truly stand apart from the crowd.

Album Recommendation: Inspectah Deck’s best work is with the Wu-Tang Clan, and he appears prominently throughout their first album.

18. DMX

Born Earl Simmons and usually known by the acronym for Dark Man X, DMX started his career in 1984. That predates many of the other rappers on this list, and he helped build his stardom by rapping on the streets of New York.  

By the time he released a major-label album in early 1998, DMX had positive reviews throughout the industry and quickly got more than five million sales. He released a second album at the end of the year, then a third at the end of 1999, all three of which debuted at #1 on the Billboard 200 and certified him as one of the top artists of the 90s.

DMX has slowed down since, releasing more albums in 2001, 2003, and 2006 before longer breaks between 2012 and 2021 releases. He died in early 2021, with the Medical Examiner’s Office ruling it a cocaine-induced heart attack. While he may still have some recorded and unreleased material, his discography is otherwise complete.

Despite the unfortunate loss of DMX, his sheer consistency of chart-topping releases makes him a worthwhile entry on this list. Very few artists can claim so many #1 albums, especially in quick succession.

Album Recommendation: DMX has plenty of good releases, but his best work is probably his third album, …And Then There Was X. However, you can just as easily start with his first album if you want to listen to his songs in order.

17. Ghostface Killah

Another member of the Wu-Tang Clan, Ghostface Killah (born Dennis Cles) rose to fame with the clan’s first album and launched his solo career with the album Ironman in 1996.

Today, he’s known for an impressively loud and fast-paced style that often mixes non-sequiturs and complex slang into stream-of-consciousness. The result is vividly colorful storytelling, which isn’t present in all other rap and distinguishes his songs from the crowd.

Ghostface Killah remains one of the most prolific rappers from the 90s, with more than a dozen studio albums and numerous other collaborations. He’s a frequent guest on albums from other artists, offering his unique style and flair to other musicians. While he’s been in movies and TV, he doesn’t do that quite as often as some other rappers.

Ghostface’s long discography means he’s an excellent artist if you want to hear a lot of music from one person. With practice, he’s also easier to pick out in collaboration songs, so you won’t run out too quickly if you actively seek his music. Few rappers, especially from the 90s, can boast quite anywhere near his number of releases.

Album Recommendation: As a member of the Wu-Tang Clan, much of Ghostface Killah’s best work is there. Notably, he provided the first verse on the group’s first song (after a chorus from RZA), as well as significant parts of several other songs.

16. Ol’ Dirty Bastard

One of the founding members of the Wu-Tang Clan, Russell Jones briefly performed as The Specialist before changing to the name he’d use for the rest of his career. His name was a dual reference to an old martial arts film and his unique rapping style.

Known for aggressively profane lyrics with an unusual half-rap, half-singing style, ODB released two main studio albums, plus a third never formally released but still made available on digital services. He died in 2004 after a drug overdose, which was a lifelong issue for him.

ODB was always closely tied to music, with GZA, RZA, and Flavor Flav as biological cousins. His relatively early death makes him one of the lesser-known members of the Wu-Tang Clan, but his lyrics and work remain a part of some of their most popular releases.

Album Recommendation: ODB doesn’t have many independent releases. If you don’t want to listen to the Wu-Tang Clan’s first album, consider his studio album Return to the 36 Chambers: The Dirty Version for more examples of his unusual style.

15. Ice Cube

Born O’Shea Jackson (and later adding Sr., after giving his son his name), Ice Cube arguably helped launch the spread of gangsta rap into truly mainstream culture with his work on the 1988 album Straight Outta Compton. He soon launched a solo career, releasing albums in 1990, 1991, and 1992 to both critical and commercial success.

Although he wouldn’t release another album in the 90s until 1998, Ice Cube’s impact at the start of the decade makes him one of its most influential members. He also has a busy life in entertainment outside of music, often appearing in at least one movie every year or two from the 90s through most of the 2010s.

Although no stranger to controversy, especially with his aggressive lyric style, Ice Cube’s skill at writing raps and directing films have ensured him a consistent place of prominence within the hip hop scene. Somewhat unusually, he also has a spot in the Rock and Roll Hall of Fame thanks to his work with N.W.A. in the late 80s. So he could also be called an 80s hip hop rapper.

Album Recommendation: Ice Cube’s third album, The Predator, stands out as his top-performing work. However, the previous album Death Certificate is also quite good and arguably the place where he hit his stride.

14. Common

Most rappers want to be anything but common, but Lonnie Lynn has embraced the name (as a shortened form of a previous name, Common Sense) following his album debut in 1992. However, it was 1994’s Resurrection that brought him critical acclaim and kickstarted his success.

Although somewhat underground throughout the 90s, he has continued growing and producing songs. Common is one of the most consistent rappers since the 90s, usually releasing an album every year or two.

Common is a highly-nominated star, with awards including several Grammys, a Golden Globe, an Academy Award, and more. His song Glory (from the movie Selma) is particularly acclaimed by critics, and is arguably his best work, though it leans more into soul music than traditional rap.

Today, Common stands out as a rather positive rapper, eschewing some of the violent lyrics of other artists in favor of pursuing his style.

Album Recommendation: Common’s sixth album, Be, is one of his best. It notably features help in production from Kanye West and is significantly better than his previous album Electric Circus.

13. RZA

The functional leader of the Wu-Tang Clan, Robert Diggs is both an outstanding rapper and one of the most notable rap producers of all time. He’s worked on numerous releases for the clan and individual members, and though described as a bit dictatorial, the group’s incredible success is in no small part due to RZA’s efforts.

A major highlight of RZA’s style is chopping up samples and either speeding them up or slowing them down to fit a beat better. He’s also quite active in television and especially film, with numerous credits in both acting and soundtrack work.

RZA is a notable fan of martial arts movies, and lesser-known is that he also enjoys chess.

While his discography is relatively short at five studio albums and another five collaboration albums, his production work is significantly longer and includes everything from single songs to entire albums. As the executive producer for some of the top songs and artists in rap, it’s nearly impossible to escape RZA’s influence in the genre.

Album Recommendation: He’s the primary producer of most of the Wu-Tang Clan’s work, so start with their first album and go from there.

12. GZA

A second founding member of the Wu-Tang Clan, alongside his cousin RZA, GZA has served as the spiritual head of the group thanks to being both the oldest member and the first one to receive a record deal. After his work with the clan, he debuted a solo album in 1995 and has managed a solo career ever since.

As indicated by one of his earlier names, The Genius, GZA is smarter than many people believe. In addition to having a particularly large vocabulary in use through his songs (beaten out only by Aesop Rock, a lesser-known artist who completely smashes the bell curve), GZA is a strong supporter of science and education.

In the years since his debut, GZA has often toured to support education, with speaking roles at Harvard and visits to major research universities like MIT. His discography is relatively short, with five studio albums, but he’s contributed to numerous other artists and albums over the years, especially with Wu-Tang Clan members.

Album Recommendation: Ditto to RZA. However, if you’re looking for something more uniquely his own, GZA’s second studio album Liquid Swords remains his best work to date.

11. Rakim

Born Willis Griffin Jr., Rakim is one of the most experienced rappers on this list, launching his first collaboration album with Eric B. in 1987. He eventually switched over to a solo career and released his first studio album in 1997.

Rakim stands out even among the crowded field of rap thanks to his technical style. Many rappers previously focused on simpler, freestyle rhymes, but Rakim sat down to write complex lyrics with internal and multisyllabic rhyming. Some rappers even credit him as the inventor of flow (complex patterns and pacing within rap).

Some publishers rate Rakim as the single greatest lyricist of all time, and even those who don’t usually have him quite high on the list. He’s worth listening to just for his impressive technical style, though his methodical pacing can sound quite different from faster singers.

Although skillful, Rakim’s discography is relatively short, with his last studio album released in 2009. His acting career is also rather limited, focusing more on music videos. Instead, he spends a lot of time working on soundtracks and helping write lyrics for others. That can make it a little hard to track down his work, but it’s often worth the effort.

For sheer technical skill and impact on hip hop, Rakim easily qualifies as one of the best 1990s rappers.

Album Recommendation: Rakim’s first studio album, The 18th Letter, is his most successful to date. Unfortunately, his sales have never quite matched his skill, but all of his works are worth listening to.

10. Missy Elliott

Melissa Elliott, who usually shortens her first name to Missy, is an active rapper and producer. She participated in several collaborative projects at the start of her career, which helped propel her debut album to number three on the Billboard 200 – the highest a female rapper had ever gotten at the time. 

Although she only released two albums in the 90s, Missy added several more over the next few years, ending with The Cookbook in 2005. Since then, she’s focused more on film, television, and production, plus participation in the occasional concert tour.

Missy is also one of the most highly-awarded rappers on this list, with four Grammys, two American Music Awards, and the distinctive status of being the first female rapper in the Songwriters Hall of Fame.

As the first Black female rapper to hit truly mainstream status in much of America, Missy stands out as an icon and inspiration for countless others within the industry. Although she’s taken a long break from music due to complications from a thyroid issue known as Graves’ disease, she has signaled interest in releasing more music in the future.

Album Recommendation: Missy Elliot’s fourth studio album, Under Construction, is the place to go if you want to hear her at her best.

9. Nas

Born Nasir Jones, Nas started his music career in 1989 and worked as a featured artist for several people in New York before releasing his debut album Illmatic through Columbia Records in 1994. While not a chart-topper, it impressed critics, and eventually went on to earn platinum certification by late 2001.

Today, Illmatic is considered an all-time top album, and his second release in 1996 topped the chart for four weeks. However, two 1999 albums were considered weaker, and he launched into a hugely public feud with Jay-Z that lasted from 2001 to 2005.

The two eventually reconciled, and Nas signed on with Jay-Z’s Def Jam Recordings to release several more albums. Despite a slightly rocky start, Nas is an extraordinarily talented lyricist and rapper, with more than a dozen studio albums released since his debut. That makes him one of the most consistent entries on this list.

Album Recommendation: Nas’ second album, It Was Written, takes the lessons from his first release and elevates his work even further, making it the best album for an introduction to his work.

8. Tupac Shakur

Also known as 2pac and Makaveli, Tupac was born in New York City but moved to the Baltimore area in 1984 and San Francisco in 1988, bursting onto the scene with his debut album 2Pacalypse Now in 1991. As a major part of the West Coast rap scene, he achieved rapid success, and the Diamond-certified All Eyes on Me from 1996 showed his range.

However, Tupac was murdered in a drive-by shooting in 1996, which remains officially unsolved. While there are some allegations, including against a gang known as the Southside Crips, it’s never been settled. The fallout from Tupac’s murder is thought to play a role in the death of The Notorious B.I.G. a few months later.

Tupac has a relatively large discography despite his short career, with four studio albums and six posthumous album releases. Notably, the double-disc Greatest Hits album, which came out in 1998, is one of just ten hip hop albums certified Diamond.

Having two diamond-certified albums despite such a short career is clear proof of Tupac’s reach. This is further amplified by his West Coast focus, in a time when the East Coast, and especially New York City, would be rising to prominence in the genre. He may well be the biggest example of what could have been in rap.

Album Recommendation: Tupac’s final album in life, All Eyez on Me, is one of his two Diamond-rated releases. His Greatest Hits album is also good, but it’s better to listen to that one second.

7. Raekwon

Born Corey Woods, Raekwon is a founding member of the Wu-Tang Clan and the creator of some staples of 90s rap. Like the rest of the clan, he also put out some solo works, starting with a studio album in 1995. Today, Raekwon usually releases an independent album every few years, making him a somewhat slow but consistent performer.

His earlier career was a little rougher when albums Immobilarity and The Lex Diamond Story garnered largely mixed reviews. However, he shot back up in 2009 with the second Cuban Linx album, where he collaborated with Busta Rhymes and RZA. His work has been broadly solid since then.

Beyond his steady music production, Raekwon often participates in music videos and soundtrack production, with the occasional movie and television appearance. He does less acting than some other rappers but remains an influential artist, especially so with anyone interested in mafioso-style rap.

Album Recommendation: Raekwon has excellent work within the Wu-Tang Clan, but if you want something of his own, his debut album Only Built 4 Cuban Link… is an exemplary display of his skill.

6. Dr. Dre

Born Andre Young, Dr. Dre is one of the standout figures in rap history. Although launched to fame as part of the gangsta rap group N.W.A., his real contribution in many ways has been his skill at producing.

Dre has worked with Snoop Dogg, Eminem, 50 Cent, and more. He works extensively with other writers for creating his songs, but while you can say many of those are a team effort, it’s his skills that bring them to the forefront.

As the producer for some of the highest-selling hip hop and rap albums of all time, Dr. Dre works more in the background than in the front. His discography is relatively short, with several collaboration albums in the late 80s and early 90s and just three studio albums in his career. Two of these were released in the 90s, though, which is why he’s on this list.

Dr. Dre is a known perfectionist with his work, which noticeably affects the production speed and quality through his label Aftermath Entertainment.

Several other rappers on this list, including Rakim and Raekwon, have tried to work with him but left without releasing something through his label. That said, practically everything he releases is top-quality, and it’s hard to argue with the results.

Album Recommendation: Dr. Dre’s second album, 2001, is a particularly good example of his work. We recommend listening to that so you can pick up his style, then listening to things he’s produced to see if you can spot his distinctive touch in various songs.

5. Scarface

Bradley Jordan was born in Houston, Texas, placing him far away from the center of rap culture in New York City. This hasn’t held him back much, especially when his time with the group Geto Boys helped propel him to fame.

Scarface started rapping earlier than many of the others on this list, allowing him to enter the 90s strong. He released five studio albums during the decade, starting with Mr. Scarface Is Back in 1991. His 2002 album The Fix is particularly notable, standing as one of the most popular albums of its time.

Although not as commercially successful as some other rappers, Scarface is popular within the industry, to the point he’s even gotten people engaged in high-profile feuds to appear on the same album together.

Scarface’s discography is relatively long, with eleven studio albums highlighting his work. However, he’s recently switched to a focus on public service, mentioning a desire to move into politics. His Positive Purpose Movement emphasizes educating children from underrepresented communities.

Album Recommendation: Scarface has plenty of good albums, but his fourth studio release, The Untouchable, is his best to date.

4. Andre 3000

Debuting in 1992 and releasing his first album in 1994, Andre 3000 is most notable as part of the Outkast duo alongside Big Boi. Together, they’ve released six collaboration albums, three of them back in the 90s. Unlike most rappers, Andre 3000 has few solo works, though he’s won several Grammys for work he’s participated in.

Andre’s work frequently features creative techniques and a mix of sounds from traditional black music genres, including funk, soul, and jungle. Andre is also notable for a more surreal and futuristic style, contrasting the violence and gangster focus of many other rappers.

Despite his comparatively short list of works, Andre 3000 has outstanding technical expertise and lyric writing ability, and even Eminem has cited him as a skillful rapper. He also has extensive work on soundtracks and appearances in numerous music videos.

In this sense, Andre 3000 is closer to a prominent supporting rapper, spending much more time helping others than creating his works. It’s impossible to deny his skill, though, and he’s worth listening to if you want to hear a different style.

Album Recommendation: Most of Andre 3000’s work is with Outkast. Of those, Speakerboxxx/The Love Below is Diamond-certified and unquestionably their best release.

3. Jay-Z

Jay-Z, born Shawn Carter, is easily one of the most influential rappers the genre has ever seen. With over 140 million records sold, literally dozens of Grammys, and an impressively long discography, he’s unquestionably one of rap’s top performers.

Although mainly active in the latter part of the 90s, with continuing work throughout the 2000s, Jay-Z’s other main contribution to the industry is his work as an entrepreneur, where he’s leveraged both fame and his cash to manage everything from clothing to sports.

Jay-Z married fellow hip hop singer Beyonce in 2008. Beyonce is independently successful, having sold over 120 million solo records, and the marriage has been unusually long-lasting and stable in an industry where shorter partnerships are common.

(Beyonce is an excellent artist in her own right, but didn’t engage in hip hop during the 90s, which is why she doesn’t have an entry on this list.)

Jay-Z is perhaps the biggest rags-to-riches story in hip hop, going from selling CDs out of his car in the mid-90s, to unquestioned superstardom. His 2017 album 4:44, notably, was his thirteenth straight studio album to debut at the top of the Billboard 200.

Album Recommendation: All of Jay-Z’s studio albums are platinum, and considering the number of them, that’s an incredible feat. However, his third album Vol. 2… Hard Knock Life is a particularly good showcase.

2. Eminem

Hip hop and rap are heavily influenced by African-American musicians, which makes Marshall Mathers III’s prominence within the industry all the more noteworthy. He released his first album, Infinite, in 1996, though it was considered a commercial failure at the time because it only sold about 70 copies.

The Slim Shady LP followed in 1999 to significantly more success, debuting second on the Billboard 200 and propelling him to fame. The album hit quadruple platinum by 2000, with a mix of hip hop, G-funk, and horrorcore styles.

Eminem often incorporates comedy into his lyrics, utilizing a large vocabulary and plenty of shock value. He also worked extensively with Dr. Dre in his earlier works, benefitting from the highly professional production values after the superstar producer noticed some lingering talent.

Today, Eminem is famous even among people who don’t know many rappers thanks to his skill at alliteration, enunciation, and lyrical complexity. His works are among the most complex in the industry, but while he’s often controversial, it’s hard to overstate his mastery of rap. Eminem stands out because he’s genuinely better than almost everyone else.

Album Recommendation: Eminem’s debut album Infinite was mixed at best, but worth listening to if you can find it before immediately moving on to The Slim Shady LP, where you’ll see the incredible improvement in his work. Outside of Infinite, all of his albums are excellent, so you can honestly start anywhere and be fine.

1. The Notorious B.I.G.

Also known popularly as Biggie Smalls, Christopher Wallace was born in 1972 and helped bring gangsta-style rap to the forefront. He released his first album in 1994 after signing with the Bad Boy Records label the previous year and helped contribute to New York’s explosive rise in the rap scene at a time when West Coast rappers were more prominent.

Despite the high quality of his releases, Biggie Smalls’ discography is relatively short due to his murder, a case that remains officially unsolved despite some allegations against various potential suspects.

With that said, many people consider him perhaps the greatest rapper of all time. The posthumous album Life After Death (which was essentially done and came out about two weeks after his death, as originally scheduled) was certified Diamond by 2000. This is a relatively rare distinction, surpassing multi-platinum and indicating ten million industry units.

Several other posthumous releases have followed, including a few that reached #1 on the Hot 100 list. He was the first to achieve this feat with two separate songs posthumously, further illustrating his ability within the industry.

The Notorious B.I.G. was planning on putting together a group known as the Commission, which notably would have included Jay-Z, but due to his death, they were never able to release a full album.

Regardless, his songs are worth listening to if you’re even slightly interested in rap. Biggie Smalls is unquestionably one of the greatest influences on the entire genre, an impact only magnified by his high-profile murder and the subsequent fallout within the genre.

Album Recommendation: Both of Biggie Smalls’ studio albums from life are outstanding releases. Life After Death is technically better, but since there are only two of them, we suggest starting with Ready to Die instead.

Top 90s Hip Hop Rappers, Final Thoughts

The 90s are truly a golden age for hip hop and rapping as a whole, showcasing the rise of many of the industry’s all-time top talents. It also showcases an incredibly dense network of collaboration between rappers, which is unusual in music but remains characteristic of their styles today. All of the 90s hip hop rappers on this list are great, so really, start anywhere you want.