The Greatest Rappers of All-Time

AKA: L Boogie

Region: East Coast

Resume: The Score (The Fugees) (1996)

Lauryn Hill may be most well known for her multi-platinum 1998 album The Miseducation of Lauryn Hill but her early work with Fugees already had her in contention for the best female rapper of all time. Hailing from South Orange, New Jersey, Hill flirted with acting in the early 90s and landed roles on the TV show As the World Turns and the 1993 film Sister Act 2: Back in the Habit where she showcased her soulful singing skills. She joined the Fugees shortly after and released the albums Blunted on Reality in 1994 and the Grammy Award-winning The Score in 1996.

Lauryn’s ability to sing beautifully, combined with a steady flow of sharply delivered rhymes, makes her a talent the likes of which we’ve never seen before or since. Her wide array of skills are perhaps best displayed with her work on the track “Ready Or Not” where she is not only responsible for one of the 90s most memorable hooks, but also raps with the distinctive flow that has her “defecating on the microphone.” If not for her public breakdown in the late 90s and a subsequent prison stint, Lauryn Hill would most likely have been on track to become the greatest selling female artist of all time.

AKA: Yeezy, Yeezus

Region: Midwest

Resume: College Dropout (2004)

While he may be better know these days for his outlandish behavior, Kanye West’s stamp on hip-hop is undeniable. From his humble beginnings as an outsider backpack rapper on his first two albums College Dropout (2004), and Late Registration (2005), to the much more experimental 2016 release Life of Pablo, Kanye has provided an endless stream of hit tracks. Early in Kanye’s career, he rapped with a chip on his shoulder after being denied by several labels and finally found a home with Rockafella after producing Jay-Z’s acclaimed Blueprint album in 2001.

Kanye’s ability to produce some of the best beats of the era is on full display with the heavily soul-sampled College Dropout and coupled with Yeezy’s expansive vocabulary and relatable lyrics, the album stands as one of the best of the 21st century. He’s been a pioneer in the progression of hip-hop over the past decade and he’s never been afraid to push the boundaries of the genre. Kanye has always been an outlier that marched to the beat of his own drum and it’s unfortunate that his antics and cold personality have clouded his legacy.

AKA: Flaco, Yasiin Bey, Black Dante

Region: East Coast

Resume: Black on Both Sides (1999)

Known for his work as part of the Brooklyn based duo Black Star alongside Talib Kweli, Mos Def would go on to have a successful solo career, as well as being featured on multiple albums throughout the late 90s and early 2000s. Mos Def’s solo debut album Black on Both Sides released in October 1999 through the Rawkus label and reached #25 on the Billboard Top 200 with the single “Ms. Fat Booty” also charting. A master of the multi-syllabic rhyme scheme that evolved from the late 80s mono-syllabic flow made popular by rappers of the time, Def’s rhymes and lyrics flow like poetry and he has a unique ability to adapt his cadence to any beat, fast or slow.

After a blossoming film career with roles in films such as Be Kind Rewind, 16 Blocks, and The Hitchhiker’s Guide to the Galaxy, Mos shifted his focus to becoming an actor but he still found time to release True Magic in 2006. In September 2011, Mos Def announced that he legally changed his name to Yasiin Bey, and has since been dedicated to social causes such as racism and the torture of prisoners in US custody. In February 2018, Yasiin Bey announced that a new Black Star project was in the works and slated for release later this year.

AKA: K-Dot, Kung Fu Kenny

Region: West Coast

Resume: Good Kid, M.A.A.D. City (2012)

Part of the next wave of West Coast rap, Kendrick Lamar bust on the scene with the 2012 album, Good Kid, M.A.A.D. City and has since cemented himself as the best rapper to come along this decade. He began to gain recognition in 2010 after his first retail release, Overly Dedicated, was well received by critics. By 2012, he had amassed a large following after collaborating with several prominent artists in the industry, including The Game, Busta Rhymes, and Snoop Dogg.

In his brief time at the forefront of rap, Kendrick has released two albums that could be considered contemporary classics with the aforementioned Good Kid, M.A.A.D. City and 2017’s DAMN. Kendrick’s style is a blend of the 90s West Coast golden era and the new generation of experimental sound we’re seeing from today’s artists. Lamar has quickly become one of the most decorated rappers of the decade with several Grammy Awards, including Album Of The Year for Good Kid, M.A.A.D. City and recently became the first rap artist to win the Pulitzer Prize for music.

AKA: Big Punisher, Moon Dog

Region: East Coast

Resume: Capital Punishment (1998)

A product of the underground hip-hop scene in The Bronx in the early 1990s, Christopher Lee Rios, known as Big Punisher, was the first Latino rapper to have an album certified platinum as a solo act. Fans were first introduced to Big Pun when he was featured on Fat Joe’s 1995 album Jealous One’s Envy and later on, the Beatnuts’ 1997 album Stone Crazy, where he spits one of the greatest opening verses ever on the track “Off The Books.” Pun’s signature flow was known for its technical efficiency, heavy use of alliteration, internal and multi-syllabic rhyming schemes, as well as needing minimal pauses to take a breath, but when he did take a breath you knew it.

After signing with Loud Records, Big Pun released his first solo album Capital Punishment in 1998 and the album was a massive hit, becoming the first album by a solo Latino rapper to go platinum. Capital Punishment peaked at #5 on the Billboard 200 and Capital Punishment was nominated for a Grammy later that year. On February 5, 2000, Rios withdrew from a planned Saturday Night Live performance with Fat Joe and Jennifer Lopez due to illness and two days later, he suffered a heart attack and was taken to a hospital where he died at the age of 28. Pun isn’t the last rapper on this list to pass away prematurely and we can only wonder what may have been if he hadn’t gone so soon.

AKA: 3000, 3 Stacks

Region: South

Resume: ATLiens (Outkast) (1996)

Atlanta rapper André Benjamin a.k.a André 3000 is known for his flamboyant style and cerebral rhymes that made him one of the most unique rappers of the 1990s and 2000s. Despite never releasing a solo album, 3 Stacks has become known as a “feature killer” over the past ten years, laying down some memorable verses for rap’s most popular acts. A member of the iconic duo Outkast which features fellow Dirty South rapper Big Boi, André 3000 was first introduced on the group’s debut release of Southernplayalisticadillacmuzik in 1994.

Outkast achieved both critical acclaim and commercial success in the 1990s and early 2000s, helping to popularize Southern hip-hop along with acts like Goodie Mob and the Ghetto Boys. Outkast, while featuring that distinct Southern sound, added their own flavor adding funk, jazz, techno, and rock elements to round out the aesthetic. There may not be a more anticipated solo album in the history of hip-hop; unfortunately, that day may never come with André publicly stating that he doesn’t want to be rapping on stage as a 50-year-old man.

AKA: The Big Fish, The Don Mega

Region: West Coast

Resume: The Predator (1992)

One of the pioneers of Gangster Rap, Ice Cube first gained notoriety as the primary songwriter and member of the iconic hip-hop group N.W.A. The group, which also featured members Easy-E, Dr. Dre, MC Ren, and DJ Yella, were known for pushing the boundaries of lyrical content in mainstream popular music. The group’s first album, Straight Outta Compton, is one of the most important releases in rap history and Ice Cube was responsible for a good amount of the lyrics, including the majority of Easy-E’s verses. While Ice Cube’s writing was on point, it was his delivery that made him one of the greatest rappers of all time.

After a contract dispute with Easy-E, Ice Cube went out on his own and released his first solo album AmeriKKKa’s Most Wanted in 1990. Ice Cube’s commanding flow was on full display when he delivered the most powerful verses in history in the opening lines of Straight Outta Compton, but he was at his best with the release of the 1992 album The Predator, which featured the classic tracks “It Was A Good Day” and “Check Yo Self.“

AKA: King of the South

Region: South

Resume: The Untouchable (1997)

There’s a good chance that Scarface is your favorite rapper’s favorite rapper. A pioneer of Southern Rap, Scarface first gained notoriety as a founding member of The Ghetto Boys which included Bushwick Bill and Willie D. The Ghetto Boys are most well known for the track “Mind Playing Tricks on Me” which is widely regarded as one of the best hip-hop songs of all time and features a powerful opening verse from Scarface. The Texas-based rapper would venture out on his own with the groundbreaking 1991 release of Mr. Scarface Is Back and his success as a solo artist would soon outshine his work with The Ghetto Boys.

The track “I’m Dead” has Scarface die at the end of the album Mr. Scarface Is Back, a dark concept that was later used by the Notorious B.I.G. on his 1994 album Ready To Die. With a career that spans nearly 30 years, the Houston legend has made a memorable impression on fans, critics, and the charts in four different decades. There’s a reason why some of the greatest rappers of all time, including Jay-Z, consider Scarface the King of The South and one of the greatest in the game.

AKA: Teacha, The Blastmaster

Region: East Coast

Resume: KRS One (1995)

A true genius and one of the greatest to ever pick up a microphone, KRS-One is a poet among rappers. In an era when artists were rapping about violence and drugs, he opted instead to deliver lyrics with a meaning and truth that captured the attention of fans and critics alike. The New York-based rapper would get his start with the group Boogie Down Productions in 1987 with the release of the album Criminal Minded alongside fellow Bronk rapper D-Nice and DJ Scott La Rock. After the shooting and subsequent death of La Rock, KRS-One began his solo career and made the shift to a more conscious and political style of rap.

With his first solo album, 1993’s Return of the Boom Bap, KRS worked together with producers DJ Premier, Kid Capri, and Showbiz, the latter being responsible for classic track “Sound of da Police.” KRS-One is known for his intellectual and technical flow and is unique in that he has the ability to hold his own in a battle against pretty much anyone on the planet. KRS has lectured at Harvard, Yale, Columbia, N.Y.U. and Stanford, which has earned him the nickname “Teacha.”

AKA: Slim Shady, Marshall Mathers

Region: Midwest

Resume: The Marshall Mathers LP (2000)

One of the few rappers on this list with the ability to hold his own in a battle rap with the world’s best (including KRS-One), Marshall Mathers a.k.a. Eminem falls just outside our top 5 rappers of all time. This Detroit, Michigan native first gained the attention of hip-hop fans with his sadistic and violent alter ego Slim Shady. The character allowed him to express his anger, with lyrics about drugs, rape, and murder, and the themes would resonate with the youth in the late 1990s. Eminem’s major label debut, The Slim Shady LP, was released in 1997 would receive positive reviews from critics earning a Grammy for Best Rap Album and quadruple-platinum status in album sales.

Eminem has sold over 170 million albums and is the best selling artist of the 2000s. While album sales alone aren’t enough for us to call him “The Greatest Rapper Of All Time” he has an undeniable set of skills that include extremely tight lyricism, which won him accolades among hardcore and casual fans of hip-hop alike. The speed at which he rattles off syllables impresses to this day and was showcased in his track 2013 Rap God, which pretty much saw Eminem declare himself a deity. Love him or hate him, Eminem is well deserving of a top 10 spot on any list of the greatest rappers of all time.

AKA: Makavelli, 2Pac

Region: West Coast

Resume: The Don Killuminati: The 7 Day Theory (Makavelli) (1996)

We have entered the sacred and highly contested top 5 of all time and while many of you are likely salty about Eminem being left out, let’s remember that this is a subjective process; everyone will have a different list. That being said, a top 5 list that doesn’t include Tupac is blasphemy. Tupac Amaru Shakur, also known as 2Pac, was born in Harlem, New York but is one of the most influential West Coast rappers of all time. Tupac’s greatness transcended the genre, with Rolling Stone ranking him 86th on its list of  The 100 Greatest Artists of All Time. In April 2017, Shakur was inducted into the Rock and Roll Hall of Fame in his first year of eligibility.

Tupac’s ability to communicate what was going on around him was second-to-none. Early on in his career, he took inspiration from the politically-charged music of Public Enemy and Ice Cube, and much of his music revolved around the violence and hardship in inner cities, racism, and other social issues. His music has inspired an entire generation of rappers, including the likes of Kendrick Lamar. Tupac’s aggressive flow and poetic lyrical skill are why many argue he is the greatest of all time.

AKA: Hova, Jigga

Region: East Coast

Resume: Reasonable Doubt (1995)

Jay-Z certainly has an impressive resume. He’s one of the best-selling musicians of all time, having sold more than 50 million albums and 75 million singles worldwide while receiving 21 Grammy Awards for his music. MTV ranked him the “Greatest MC of all time” in 2006 and Rolling Stone magazine ranked three of his albums— Reasonable Doubt (1996), The Blueprint (2001), and The Black Album (2003)—among The 500 Greatest Albums of All Time. Jay-Z is also the first rapper to be inducted in the Songwriters Hall Of Fame, an accolade that speaks to his excellence and longevity in the rap game. As we mentioned earlier though, album sales and awards are only part of the formula that gives a rapper a spot in our top 15.

Fortunately, Jay-Z has emerged as that rare artist that has successfully melded street cred, popular mass appeal, swagger, and the classic American rags-to-riches storyline that has made him a fixture since his 1996 debut Reasonable Doubt. With a career that has spanned three decades, Jay-Z has connected with hip-hop fans through his lyrical wizardry that features rhymes about everything from living the street life to living large.

AKA: Esco, Nasty Nas

Region: East Coast

Resume: It Was Written (1996)

Nas unleashed the fury on Jay-Z during their late 90s rap beef with “Ether,” a diss track so lethal that its title has become hip-hop shorthand for lyrical annihilation. While Nas was already considered one of the greatest rappers of all time, he cemented his place ahead of Jay-Z in our top 5. A native of Queens, New York, Nas exploded on to the scene with his 1991 debut Illmatic, which was universally praised by critics and the hip-hop community. While Illmatic was Nas’ introduction to most hip-hop fans, hardcore fans got their first taste of Nas’ skill with his collaboration on Main Source’s 1991 track Live at the Barbecue. Never has there been a rapper who could create so much hype from a 16-line verse and Nas rode that wave into the successful launch of his career.

Illmatic introduced us to Nas’ poetic lyrics and surreal flow that would have hip-hop fans excited to see what he would do next. Nas’s follow-up, It Was Written, debuted at #1 on the Billboard 200 and remained on top for four consecutive weeks reaching Double Platinum status in two months and made Nas internationally recognized. Ranked by The Source as the #2 lyricist on their list of the “Top 50 Lyricists of All Time”, Nas has eight consecutive platinum and multi-platinum albums with over 25 million records sold worldwide.

AKA: Biggie, Biggie Smalls

Region: East Coast

Resume: Life After Death (1997)

A legend who built his legacy upon the strength of freestyle battles throughout the New York borough of Brooklyn, Christopher Wallace a.k.a. The Notorious B.I.G. would become a rap icon during his short-lived career and life. Born of Jamaican descent, B.I.G.’s booming voice featured a hint of patois that dominated the streets and airwaves in the 90s. With the aid of Sean “Puffy” Combs, the pair created a portly playboy persona with a thirst for beautiful women, fancy cars, fine dining, and expensive property. A central component to the East Coast vs.West Coast rivalry, his involvement would set off a chain of events that would eventually lead to his murder in 1997 at the age of 25.

Biggie’s debut album Ready to Die released in 1994, reached No. 13 on the Billboard 200 chart, and eventually went quadruple platinum. His follow up album Life After Death released on March 25, 1997, 16 days after his death. The monumental album rose to No. 1 on the U.S. album charts and was certified diamond in 2000 by the Recording Industry Association of America, one of the few hip-hop albums to receive this certification. The Notorious B.I.G. was one of the few artists that had both mainstream appeal and street credit that bled through into his rhymes. Unfortunately, he left us too soon and hip-hop fans are left wondering what may have been.

AKA: The God MC, Rakim Allah

Region: East Coast

Resume: The 18th Letter (1996)

Rakim was the pioneer of the internal rhyme scheme and the history of hip-hop can be divided into the pre and post-Rakim eras. He elevated rap from an era known for their simplistic patterns which mainly revolved around party themes, introduced a higher standard of lyricism. He reinvented the genre and gave birth to a more complex form of lyricism influencing every rapper that came after him. Rakim first rose to fame with his early collaboration with fellow New York native and DJ, Eric B. The album Paid in Full released in 1987 and was an instant classic, featuring some of the greatest and most sampled rap songs of all time.

Rakim’s razor-sharp lyrics were like nothing hip-hop fans had ever heard before and would transform the airwaves in subsequent years. His smooth and laid back cadence and flow would be studied and replicated by up and coming rappers like Nas, The Notorious B.I.G, and Jay-Z. Rakim has been at the top of the mountain for decades with The Source Magazine ranking him #1 on their list of the “Top 50 Lyricists of All Time” in 2012. Simply put, Rakim single handily changed rap and is directly responsible for many of the rappers on this list.