How Hip-Hop’s Biggest Icons Have Changed Over The Years

Mason Zimmer | June 22, 2024 5:54 pm

Although this is often true of the music industry in general, hip-hop has been historically regarded as a young artist's game. It's a genre that thrives on energy, image, and the insight gleaned from fresh perspectives. So, for a rapper to avoid becoming a flash in the pan, they have to be iconic enough to achieve true longevity.

Although that's a hard tightrope to walk, it isn't impossible. Although these rap legends have had varying degrees of success after their commercial peaks, the fact that they were able to survive the trends they rode in on shows there was always something special about them.

Dr. Dre

Dr. Dre
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After emerging as an electrifying young beat producer and rapper during his stint in the legendary rap group N.W.A., Dr. Dre found even greater success with his first solo project, The Chronic, in 1992. However, issues with the management of Death Row Records led him to strike out on his own and found Aftermath Entertainment, through which he made the red-hot sophomore effort 2001.

Although rap fans awaited his third album, Detox, for over 15 years after this, Dr. Dre eventually shelved the project in favor of Compton, a 2015 release that was paired with the N.W.A. biopic Straight Outta Compton. As HuffPost reported, however, he hasn't needed to make much music after the success of his Beats line of headphones, which nearly made him a billionaire after he sold the brand to Apple.

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Eminem

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After he exploded on the scene in 1999, both those within and outside of the hip-hop community weren't sure what to do with Eminem. Although he demonstrated his immense creativity and impressive technical skills on records like The Slim Shady LP and The Marshall Mathers LP, his lyrics attracted no end of controversy, and his subject matter was wildly different from what typically prevailed in mainstream hip-hop.

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Although he experienced a creative slump soon after the album The Eminem Show and the film 8 Mile took him to the height of his career, he successfully rebounded with the album Recovery in 2010. This ushered in an area of a more mature Eminem, albeit one who's less prolific and less commercially successful. But while he hasn't recorded an album since 2020, his performances at the Oscars and the Superbowl have only confirmed his legacy.

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Snoop Dogg

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After rocketing to prominence by collaborating with Dr. Dre on the 1992 album The Chronic, Snoop Dogg showed he could carry a successful career on his own with the album Doggystyle. Although the decade that followed was tumultuous enough to see him leave two different record labels, he stayed on top with successful tracks like "Beautiful" and "Drop It Like It's Hot" in the 2000s.

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Although Snoop Dogg hasn't had a song chart since "Young, Wild & Free" with Wiz Khalifa and Bruno Mars in 2011, his career has since become so multi-faceted that music stopped being the main engine of his success over a decade ago. Between movie and TV appearances, long-time collaborations with Martha Stewart, and even a short stint on gaming brand FaZe Clan's board of directors, Snoop Dogg is as much of a public figure as he's ever been. According to NPR, he even owns the label that gave him his start, Death Row Records.

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Lil Kim

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After first making her name as a protégé of slain legend The Notorious B.I.G. and a member of Junior M.A.F.I.A., Lil Kim found success of her own during the late '90s and 2000s with her blend of racy and hardcore lyrics and her confident delivery.

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Although her last appearance on the Billboard Hot 100 saw her featured on the Keyshia Cole song "Let It Go" in 2007, Lil Kim stayed active throughout the 2010s. According to Allmusic.com, she has since gone independent and released the mixtapes Black Friday, Hard Core 2K14, and Lil Kim Season before making her most recent album, 9, in 2019.

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50 Cent

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After building some buzz in New York City, 50 Cent conquered 2003 with his best-selling and best-regarded major label debut, Get Rich Or Die Tryin'. According to The Guardian, the album sold 12 million copies that year, which not only made him a millionaire but seemed to give him a rap empire for a few years.

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Although his follow-ups, The Massacre and Curtis, both went platinum, 50 Cent was already seeing diminishing returns from his music by his third album. However, his stake in the Vitamin Water manufacturer Glaceau ended up making him at least $60 million when it sold to Coca-Cola, and he moved on to acting in films and TV and producing his own TV show, Power. Like many elder statesmen in rap, he's more of a business mogul than an artist nowadays.

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Missy Elliot

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After scoring her first platinum album, Supa Dupa Fly, in 1997 and rising to fame alongside the producer Timbaland and R&B singer Aaliyah, Missy Elliot released a series of acclaimed and commercially successful albums that included Miss E … So Addictive in 2001, Under Construction in 2002, and The Cookbook in 2005. According to A&E's Biography website, she also won five Grammy awards throughout her legendary run in the 200s.

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However, that run was cut short by Grave's disease, which she would focus on battling for several years. Regardless, she was able to stage a successful return to the spotlight after her 2015 Superbowl Halftime Show performance, which she followed up with the gold-selling single "WTF." In 2019, she dropped the EP Iconology, which would be her first record in 14 years.

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Lil Wayne

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Although he was already a famous rapper as a young teen due to his membership in the New Orleans group Hot Boyz, Lil Wayne's star wouldn't truly rise until the 2000s. During that time, a combination of his popular Tha Carter album series and an incredibly prolific run of mixtapes led to his self-proclaimed status as "the best rapper alive."

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His ill-fated 2010 rock album Rebirth and a string of shakier projects like Tha Carter IV and some disappointing sequels to popular mixtapes like Dedication and I Am Not A Human Being tarnished Lil Wayne's legend for a time. But after he regained some form with Tha Carter V in 2018, has remained active and celebrated in the years since. Most recently, he released a collaboration album with 2 Chaniz called Welcome 2 Collegrove.

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Lauryn Hill

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After emerging as the breakout star of beloved, eclectic New Jersey hip-hop collective The Fugees, Lauryn Hill went solo and released The Miseducation Of Lauryn Hill in 1998. According to the Berklee College of Music, this critically adored and incredibly successful album reached diamond status in 2011, making Hill the first female rapper to sell over 10 million copies of an album.

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However, the aftermath of this release would apparently throw her into a creative drought that still hasn't abated 25 years later. Although People reported that she and the reformed Fugees can still play to sold-out venues, the only follow-up she's had to her debut has been the ill-fated live recording of her erratic MTV Unplugged No. 2.0 performance in 2001.

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Ice Cube

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Ice Cube first established himself as a brash, fearless rapper while serving as a member of the group N.W.A., for whom he was the primary lyricist. However, he would find just as much success following his split with the group and emerged as an acclaimed yet controversial artist due to his incisive, often inflammatory lyrics.

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But while the early '90s saw a legendary run of albums in AmeriKKKa's Most Wanted, Death Certificate, and The Predator, movies like Boyz In The Hood and Friday also showed that he'd have a viable career as an actor. And while he would continue making albums until 2018's Everythangs Corrupt, he would largely focus on his film work once the success of his rap career waned.

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Kendrick Lamar

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After some introductory mixtapes and the release of his first album, Section .80, in 2011, Kendrick Lamar's impressive vocal dexterity and his complex, thought-provoking lyrics positioned him as one of the most exciting new voices in hip-hop. And after the release of his beloved Good Kid, M.A.A.D. City album during the following year, fans were already prepared to name him as one of the best rappers to ever live.

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But if that hype seemed premature at the time, the West Coast scion's further releases would only solidify his legend. His 2015 release, To Pimp A Butterfly, is widely regarded as one of the best rap albums of all time, and according to NPR, his 2017 album DAMN made him the only rapper to receive a Pulitzer Prize for their music. And the 2020s have proved fruitful for him as well, since his 2022 release Mr. Morale & the Big Steppers, and his collaborations with his cousin Baby Keem have both continued his eye-catching momentum.

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Nicki Minaj

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Of the strength of her mixtapes in the late 2000s, Nicki Minaj found herself on Lil Wayne's Young Money label, where she stood out for her unpredictable shifts in tone and persona during her verses and her clear talent for rapping. Although Billboard reported that her Pink Friday series of albums in the early 2010s afforded her multiple top 10 hits and Grammy nominations, it was often unclear as to whether she was making rap or pop albums.

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Her verse on Doja Cat's "Say So" secured her status and means she has now performed on a number-one hit, but Minaj's albums have consistently sat at the top of Billboard's album charts. In fact, the organization reported that with the release of Pink Friday 2 in 2023, she became the first female rapper to have three albums debut at number one and to have albums achieve this feat in subsequent decades.

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Jay-Z

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After releasing the classic album Reasonable Doubt under his independent Rocafella Records label, Jay-Z found a path to superstardom that was paved by his In My Lifetime album series. He scored massive hits with "Hard Knock Life" and "Big Pimpin'" before making The Blueprint, a 2001 album that is widely considered his masterpiece.

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After scoring major hits with "99 Problems" and "Dirt Off Your Shoulder" from his 2003 record The Black Album, Jay-Z announced his retirement from hip-hop. Of course, this was notoriously short-lived, as he would return to rap in 2006. Not only has he seen further success with songs like "Empire State Of Mind" and the album 4:44, but he's also become a sports and entertainment mogul through his Roc Nation brand.

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Eve

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Cutting an image as the tough, no-nonsense First Lady of DMX's Ruff Ryders label, Eve achieved international success in the early 2000s with her brand of confident, unbothered rap. She appeared on several top ten hits between 2001 and 2004, two of which being collaborations with former No Doubt lead singer Gwen Stefani.

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But while her albums Scorpion and Let There Be Eve sold well thanks to "Let Me Blow Ya Mind" and "Gangsta Lovin," she told The Guardian that a lack of interest in her 2013 release Lip Lock led her to retreat from the music industry. Although she still performs and has started a family with billionaire Maximillion Cooper, she hasn't released an album since then.

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Nelly

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At once smooth and energetic, St. Louis rapper Nelly blazed a fascinating trail as one of the first hip-hop artists from the Midwest to reach stardom and take pride in his rural roots. According to Billboard, Nelly secured four top-ten hits by 2003, two of which went to number one and remained there for weeks at a time.

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The Bad Boys 2 tie-in "Shake Ya Tailfeather" stayed atop the charts for four weeks, while the slow jam, "Dilemma," reigned for a staggering ten weeks. But while Nelly's commercial success would continue with his twin 2004 releases, Sweat and Suit, his career would largely slow down after this, save for a collaboration with the country band Floria Georgia Line on 2012's "Cruise."

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Busta Rhymes

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When he made his mark in the hip-hop world with his breakout single, "Woo-Hah!! Got You All in Check," Busta Rhymes stood out as a unique presence with his intensely animated and high-speed delivery. And while his biggest hits were great for starting a party, he maintained his albums retained respect among hardcore rap listeners with their apocalyptic tone and subject matter.

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And while he's continued to bring this energy to the 2020s with the album Extinction Level Event 2: The Wrath Of God, Busta Rhymes's career has since had its share of ups and downs due to the struggles of finding the right label in the 2000s and the 2010s. As he told Sway on SiriusXM radio, creative differences at both Aftermath Entertainment and Cash Money Records made his stints there fairly short-lived.

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Foxy Brown

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In many ways, Brooklyn rapper Foxy Brown didn't have a particularly lucky career. For each step forward she took as an artist, there seemed to be a setback. Although she scored a top ten hit with "I'll Be" from her debut album Il Na Na, secured high-profile collaborations with Jay-Z, and formed a whole supergroup with Nas, each achievement was tarnished in some way.

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Not only did no follow-up album reach the commercial and critical reception that Il Na Na did, but she was repeatedly accused of having her lyrics ghostwritten by Jay-Z, and the supergroup ended up splitting up after one ill-fated album. However, the worst spate of luck came in 2005, when MTV reported that she experienced a sudden and near-total loss of her hearing. Although she would regain her hearing thanks to surgery in the following year, her career never recovered from this setback.

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Drake

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After releasing his breakthrough So Far Gone mixtape in 2009, Toronto rapper Drake's blend of braggadocios rapping, smooth singing, and vulnerable, emotional songwriting made him a fresh new voice in hip-hop. And it scored him two top-ten hits in "Best I Ever Had" and "Forever," but these would only be the first of many.

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If Drake's career was starting to get big back then, it's only become titanic in the years since. About 15 years after this promising start, Billboard has credited Drake with 76 top-ten hits and 13 number-one hits. Variety reported that the most recent of these, 2023's "First Person Shooter," has tied Drake with Michael Jackson for the most number-one hits scored by a solo male artist.

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Method Man

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One of the rising stars of the legendary Wu-Tang Clan, Method Man, made a number of successful moves that made him a successful rapper and actor. Not only was his work with the powerhouse group deserving of its own acclaim, but solo records like Tical and his frequent collaborations with New Jersey rapper Redman would further elevate both of them into prominence.

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Although their album Blackout! was a fondly remembered success, their movie How High also put Method Man on the radar as an actor. This opened the door for more challenging roles like his recurring role in the celebrated crime series The Wire. Although Method Man hasn't released an album since 2018 and hasn't had a song chart since 2003, these accolades have put an impressive legacy behind anything he seeks to try next.

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Nas

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Nas broke into the major hip-hop scene in 1994 with Illmatic, which remains widely regarded as the best hip-hop album of all time. But while his 1996 follow-up It Was Written continued his commercial and critical momentum, his career would enter a slump afterward that was righted in 2001 by his explosive diss track toward Jay-Z called "Ether."

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Unlike many other artists who have been in the rap game for over 30 years, Nas remains as productive and acclaimed as he was during his auspicious start. His recent King's Disease album series has earned him a Grammy nomination every year like clockwork since 2021, and the first of this trilogy finally saw him win the award in a career that has included 17 nominations.

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André 3000

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Although both members of the Atlanta group Outkast proved to be gifted rappers and songwriters, André 3000 stood out as an unpredictable presence who combined his smooth delivery with sophisticated yet relatable lyrics. Yet, as his time with the group progressed, he found himself feeling limited by rap and more interested in exploring other genres.

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This was evident on Outkast's diamond-selling Speakerboxxx/The Love Below record, but it also appeared to underscore a curious career that only saw him make rare, if welcome, appearances on other rapper's songs. However, fans who awaited an André 3000 solo release finally got their wish in 2023 when he released the unexpected but celebrated New Blue Sun, which saw him step away from vocal performances to play the flute. Billboard reported that a 12-minute track from this release charted on the Hot 100.

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Queen Latifah

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After arising alongside the socially conscious Native Tongues movement in the late '80s and early '90s, Queen Latifah established herself as a powerful presence as a rapper while also flaunting her chops as a singer. At the same time, she also demonstrated her likability and acting talents in movies like Set It Off and her role in the sitcom Living Single. But perhaps her most iconic film role saw her portray Matron "Mama" Morton in the film adaptation of Chicago.

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Not only would Queen Latifah become more prominent in Hollywood after this role but her music would change and see her pursue vocal jazz and R&B throughout the 2000s. Although Billboard noted that her 2009 return to rap, Persona, charted higher on the Top Hip-Hop/R&B album charts than any of her previous efforts, she's mostly committed to acting in and producing movies and television nowadays.

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J. Cole

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After amassing some serious buzz on the mixtape circuit, North Carolina rapper J. Cole's long-awaited major label debut, Cole World: The Sideline Story, was released by Roc Nation. But while the album showed his promise as an artist, singles like "Work Out" suggested a compromised vision that famously disappointed Nas, which he addressed on his follow-up record, Born Sinner.

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In the years since this mixed start, however, J. Cole seems to have firmly shed his growing pains as an artist. Not only has Billboard credited him with 12 top-ten hits in the decade since, but he has seen success by starting his Dreamville record label, which is now a home for rising stars like Ari Lennox, Earthgang, and JID.

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Da Brat

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After emerging as a rising star on Jermaine Dupri's So So Def label with her 1994 debut, Funkdafied, Da Brat's brash and defiant delivery secured her a top-ten hit with the album's title track. She would then attain some further play with her 2000 summer anthem "What 'Chu Like" and appear on the big Dem Franchize Boyz hit "I Think They Like Me" in 2005, but would only sporadically release music after that.

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Indeed, Da Brat's career was already on a downward trend by the time "I Think They Like Me" came out, and in 2005, she would have been more recently known for appearing on the MTV reality show The Surreal Life than for her music. But while her career may have slowed since her heyday, People reported that she has recently started a family with her wife Jesseca Harris-Dupart.

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Ludacris

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Known for his crude yet clever lyrics and his larger-than-life and aggressive (yet still party-friendly) delivery, Ludacris was all but the face of mainstream rap during the early 2000s. He was also one of the voices credited for ushering in the rise of southern hip-hop during that period, alongside Outkast and the crunk movement spearheaded by Lil Jon.

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But while albums like Word Of Mouf, Chicken & Beer, and the Red Light District gave Ludacris a string of best sellers, his success would become more inconsistent by the time he released Theater Of The Mind in 2008. However, he pursued an acting career concurrently with his rap career, which has continued to bring Ludacris more reliable success thanks to the Fast and Furious franchise.

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LL Cool J

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One of hip-hop's first superstars, LL Cool J set the old-school rap world on fire with his 1985 debut Radio, which made "Rock The Bells" one of his enduring signature songs. And while he would see a slight dip with his third release, Walking With A Panther, he re-established himself as a force to be reckoned with via his explosive 1990 release, Mama Said Knock You Out. Although his rap career would continue to considerable success throughout the '90s and moderate success in the 2000s, LL Cool J would also act in movies like Deep Blue Sea.

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However, his later career was dominated by his starring role in NCIS: Los Angeles, which began in 2009 before the show wrapped up in 2023. Since the most noteworthy music project for LL Cool J since then was an incredibly ill-conceived collaboration with country singer Brad Paisley in 2013, it's little surprise that the world of television has attracted more of his focus than his music over the last decade.

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Common

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Also known as Common Sense, Chicago rapper Common attracted widespread acclaim within rap circles through his ambitious, sophisticated albums like 1994's Resurrection and 2000's Like Water For Chocolate. His career would receive an even bigger boost with the critically acclaimed 2005 record Be, which allowed him to amass enough cultural capital to start a high-profile acting career as well.

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In the years that followed, Common would record a respectable collection of albums from 2007 to 2021 that — with the exception of 2008's Universal Mind Control — consistently garnered positive reviews and maintained his respect among his fans. At the same time, Common secured high-profile roles in films like American Gangster, John Wick: Chapter 2, and Selma, the latter of which saw him collaborate with John Legend on the Oscar-winning original song "Glory."

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Jean Grae

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Although she's always been associated more with positive word-of-mouth and critical perception rather than mainstream success, Jean Grae has long been celebrated for her dense, complex lyricism and ambitious song concepts. According to AllMusic, however, her disillusionment with the music industry following the long-time delay of her album Jeanius prompted her to announce her retirement from music.

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As is often the case in rap, however, this retirement was temporary. After her engagement with fellow underground rapper Quelle Chris, the pair would collaborate on 2018's Everything's Fine. The album is darkly humorous, with guest appearances from comedians John Hodgman and Hannibal Buress, but its subject matter makes it abundantly clear that the title is ironic.

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Ice-T

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A pioneering force in gangster rap who's represented South Central Los Angeles since the late '80s, Ice-T first attracted recognition within the hip-hop community with his sprawling anthem "6 'N the Mornin'," which saw him run from the law. As Ice-T's career both as a solo rapper and as the frontman of the hard rock band Body Count progressed, his lyrics made him the subject of frequent controversy that reached a fever pitch with the latter project's infamous song, "Cop Killer."

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Although Ice-T would continue releasing albums until 2006 as a solo rapper and until 2020 with Body Count, his most lucrative and prominent gig after this controversy would be an ironic one. Although one of his earliest movie roles saw him co-star in the 1991 crime film New Jack City, his most long-running acting role has seen him play Detective Odafin 'Fin' Tutuola (now Sergeant) on Law And Order: Special Victims Unit for over 20 years.

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Will Smith

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Although Will Smith's acting career has long overshadowed his rap career, Will Smith's start in show business nonetheless came as a result of his collaborations with DJ Jazzy Jeff as the Fresh Prince. Not only did this result in hits like "Parents Just Don't Understand" and "Summertime," but it afforded Smith a foothold into the acting world with The Fresh Prince Of Bel Air.

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And while movies like Independence Day and Men In Black would rocket his film career to prominence during the '90s, he was able to maintain success as a rapper by taking a family-friendly tack on albums like Big Willie Style and Willennium. However, interest in his records started to wane by the time he released his last album, 2005's Lost And Found, and he pursued acting full-time, leading to an eventual (if tumultuous) Oscar win in 2022.

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MC Lyte

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A pioneering female rapper and among the first to address misogyny in hip-hop in her lyrics, MC Lyte emerged as a hard-hitting, confident presence on her 1988 debut, Lyte As A Rock. Although that album remains a classic part of hip-hop history, Billboard reported that MC Lyte wouldn't start seeing much commercial success for her work until the '90s.

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Her highest-charting hits would come from the 1996 album Bad as I Wanna B, and only "Keep On, Keepin' On" from that record would crack the top ten. AllMusic described MC Lyte as being active in anti-violence campaigns, various benefits to fund AIDS research, and the Rock the Vote nonprofit organization. However, she hasn't recorded any new music since 2003.

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The Game

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Although The Game first entered the scene as a Dr. Dre protégé known for his raspy voice, emotionally raw lyrics, and reverence for the history of West Coast hip-hop, his name would often be associated with drama in the decades that followed. This began with an acrimonious split from 50 Cent's G-Unit group but would also see him engage in often one-sided beefs with the likes of Jay-Z and Eminem.

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Nonetheless, The Game would remain prolific throughout the troubles and notch charting singles on the albums The Doctor's Advocate, L.A.X, and The R.E.D. Album. Although Billboard's data indicates that none of these singles charted as high as "Hate It Or Love It" and "How We Do" from his multi-platinum debut, The Documentary, The Game has the distinction of charting as recently as 2022 with the controversial single, "Eazy."

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Remy Ma

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According to People, Remy Ma's first major appearance came on the legendary late rapper Big Pun's final album Yeeeah Baby, where she showed her skills on the song "Ms. Martion." This would lead to a long-term stint on the group Terror Squad, which Brox rapper Fat Joe started with Big Pun. This position led Remy Ma to a high-profile verse on the 2004 hit "Lean Back."

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Although Remy Ma first entered the Billboard charts on her own with "Conceited" in 2006, it would take until 2016 when her name appeared on the Hot 100 list again, this time as a featured artist on Fate Joe's 2016 sing, "All The Way Up." According to People, that year would be big for her for another reason, as she married fellow rapper Papoose during an episode of Love & Hip-Hop. She would also enter a public feud with Nicki Minaj the following year, which inspired the viral song "Shether."

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Flavor Flav

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Although HipHopDX confirmed that Flavor Flav has been a wunderkind multi-instrumentalist for the length of the legendary rap group Public Enemy's impressive decades-spanning run, he's more commonly regarded as the group's hype man. This is a valuable role in and of itself, as the fiery political bleakness of his main bandmate, Chuck D, mixes well with his vivacious, humorous style.

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Although Public Enemy's initial run of albums that included It Takes a Nation Of Millions To Hold Us Back, and Fear Of A Black Planet is often the most fondly regarded portion in the group's extensive catalog, Flavor Flav and Chuck D have managed to stay recording at a consistent level of quality as recently as 2020. Flavor Flav's larger-than-life personality also brought him significant reality TV popularity on The Surreal Life and The Flavor Of Love.

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Diddy

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Although Sean Combs has gone through the names Puff Daddy and P. Diddy before simply landing on "Diddy," he's been a powerful figure in hip-hop through each stage of his nomenclature. He's released nine albums to various success over the course of his rap career, but he's been known more as a businessman than as a rapper since at least the early 2000s.

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This is not only because he founded the Bad Boy record label that produced The Notorious B.I.G.'s legendary albums but also because of the success of his Sean John clothing line. Although Forbes reported that his brand partnership with alcohol manufacturer Diageo has since ended on less-than-friendly terms, that was also a major revenue stream for him for years.

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Tyler, The Creator

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In the late 2000s and early 2010s, Tyler, The Creator rode a wave of controversy and hype in the company of Odd Future, a rap and skateboarding collective that included fellow acclaimed artists Frank Ocean and Earl Sweatshirt. This period saw Tyler make edgy and dark music with a humorous bent to it, which he and his collaborators parlayed into an Adult Swim sketch comedy show called Loiter Squad.

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But while the provocative video and homophobic lyrics in his song "Yonkers" earned him as much backlash as buzz, Tyler's creative ambitions have since all but left his more immature music in the dust. Through acclaimed albums like Flower Boy, Igor, and Call Me If You Get Lost, Tyler, The Creator has proven his mettle as a composer and songwriter who can work just as comfortably outside of rap as within the genre's limits.

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MC Hammer

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Although acts like Run DMC and LL Cool J had found stardom in hip-hop before MC Hammer's rise in 1990, it was hard to name a rap song that had ever gotten as big as "U Can't Touch This" by the time it came out. And while the Billboard Database noted that songs like "Pray" and "2 Legit 2 Quit" actually charted higher than his signature song, it nonetheless practically defined the pop-rap of the early '90s.

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However, Entertainment Weekly reported that by 1996, MC Hammer had filed for bankruptcy after his lavish (and often generous) lifestyle came face-to-face with a sea change in rap that saw gangster rap grab dollars and attention that once belonged to him. Although he tried to adapt to this with 1994's The Funky Headhunter and kept making albums as late as 2001, his career is more rooted in nostalgia than driven by any recent efforts nowadays.

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T.I.

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Known for his confident yet laid-back flows and lyrics about overcoming the challenges of street life by hustling hard, AllMusic explained that T.I.I practiced what he preaches by aggressively selling mixtapes until he returned to prominence following the failure of his first major label deal. T.I.'s critical acclaim, commercial success, and street respect throughout the 2000s threw some credibility behind the self-proclaimed King Of The South's claim to the throne.

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While the 2003 album Trap Muzik introduced T.I. to the world with his signature "Rubber Band Man" song, even more successful albums like 2006's King and 2008's Paper Trail would produce four top-ten hits between them, with "Dead And Gone" and "Live Your Life" both reaching number one on the Billboard Hot 100. But while he has continued releasing albums as late as 2020, only one single from that year's The L.I.B.R.A charted at number 97.

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Pusha T

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After spending seven years making music with his brother Malice as part of the Virginia Beach group Clipse, Pusha T struck out on his own and signed with the G.O.O.D. Music record label. Although his highest-charting songs would involve featured spots on other artists' work, his albums have become more acclaimed among fans and critics alike than the last.

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Although Variety reported that Pusha T cut all ties with G.O.O.D. Music after the release of his 2022 record It's Almost Dry, both that and his previous album Infrared are among his most celebrated releases. The period between those album cycles also saw him strike a devastating blow to Drake's public image with the methodical diss track "The Story Of Adidon" in 2018.

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Rapsody

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After a long period of working with acclaimed producer 9th Wonder, North Carolina rapper Rapsody bridged the long gap between her 2012 album The Idea of Beautiful and her 2017 release Laila's Wisdom with a series of mixtapes. According to AllMusic, these attracted significant enough underground buzz to see her work with major rap stars like Kendrick Lamar and fellow North Carolina native J. Cole.

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But while Billboard noted that Laila's Wisdom didn't quite crack their Hot 100 list, her follow-up album Eve performed significantly better. Although it took her some time to get here, Rapsody seems to be gaining prominence and success as a rapper, which makes her future look bright. Now, the only question is what she'll do next.

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Ja Rule

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Although the peak of Ja Rule's career didn't last long, he was nonetheless able to notch five top-ten hits — with one called "Always On Time" even making it to number one — while appearing on two number-one hits by Jennifer Lopez between 2000 and 2004. The secret to his success was the way he and his management paired up Ja Rule's gruff, deep vocals with the dulcet tones of various R&B singers (especially Ashanti).

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However, that success would become short-lived after an ill-fated beef with 50 Cent and Eminem severely damaged his public perception as a credible rapper and arguably contributed to the ruin of his label, Murder Inc. Although he released albums until 2012, he never had another hit again. And according to People, his non-musical projects haven't always gone smoothly either because he was unfortunate enough to be the co-founder of the infamous Fyre Fest in 2017.