50 Greatest Rap Groups of All Time

Thanks to their hard-nosed demeanor and gruff wordplay, Brooklyn duo M.O.P. — rappers Lil Fame and Billy Danze — have proven their status on the East Coast circuit for more than 25 years. For 1998 album  First Family 4 Life, they secured rap stalwarts such as Jay-Z, Gang Starr and Naughty By Nature’s Treach and enlisted DJ Premier’s production prowess. In 2000, the pair reached their apex with their biggest hit to date, “Ante Up.” The bombastic track was a gumbo of brash energy and explosive production, a classic which later morphed into an even more indelible remix featuring Busta Rhymes, Remy Ma and Teflon.  — CARL LAMARRE

Proud descendants of the Black cultural and human experience, Brooklynites Mos Def and Talib Kweli stood as inheritors of the grand hip-hop tradition. They were also representative of artists rejecting the overt violence characterizing the Notorious B.I.G. and Tupac era of hip-hop. Taking their name from Black activist Marcus Garvey — and sprinkling references to Black music icons like Slick Rick, Erykah Badu and Gil Scott-Heron into their free-flowing bars/rhymes — they broke through with 1998’s Mos Def & Talib Kweli Are Black Star. The critically adored set was a crystal-clear distillation of that late-’90s sentiment, presented by two lyrically deft MCs and flow innovators, containing layers that still deliver new insights 25 years later. A follow-up album finally arrived in 2022 — but even if their output was limited to just that first, singular document, Black Star deserves its place in the pantheon. — DAN RYS

Longtime best friends Yung Miami and JT joined forces in the late 2010s to become rap’s rambunctious It-girls. The City Girls effused their addictive IDGAF energy through ratchet, bass-bumping club anthems filled with charismatic, cocksure bars about using men for money and splurging on name brands. “F–k that Netflix and chill – what’s your net-net-net worth?” Yung Miami rapped on Drake’s Billboard Hot 100-topping “In My Feelings,” for one of the group’s biggest crossover moments. Since then, the two have continuously promoted uncensored, sex-positive rap through platinum singles like “P—y Talk,” while expanding their storytelling skills into TV by executive producing Issa Rae’s HBO series Rap Sh!t. — HERAN MAMO

From the beginning, Rae Sremmurd had their creative formula down pat: Swae Lee floating across melodies; Slim Jxmmi croaking out pummeling bars. Together, the Tupelo, Miss. sibling duo specialized in hypnotically minimal party-starters like “No Flex Zone” and “No Type.” Yet Rae Sremmurd transcended their initial blueprint by evolving alongside each other — hits like “Powerglide” and the Hot 100-topping “Black Beatles” stretched outward while folding in guests Gucci Mane and Juicy J, respectively. And they also evolved separately, as 2018’s SR3MM gave Swae and Jxmmi their own solo albums, while a joint third disc plugged back into the duo’s powerful chemistry. — JASON LIPSHUTZ

The Ying Yang Twins reigned supreme over nightclubs, radio stations and middle school dances of the early 21st century after their 2000 debut single, “Whistle While You Twurk.” The Atlanta duo – consisting of not-brothers Kaine and D-Roc – followed that breakthrough with an epic string of party singles and collaborations: “Salt Shaker,” “Wait (The Whisper Song),” “Shake” with Pitbull and their unforgettable feature on Lil Jon & the East Side Boyz’s game-changer “Get Low.” The Ying Yang Twins’ crossover success was so undeniable that even pop princess Britney Spears enlisted the pair for her hip-hop-flavored In the Zone deep cut “(I Got That) Boom Boom.” With their gritty chants, earworm hooks and iconic ad-libs (“Ah, up!”), Kaine and D-Roc’s role in bringing southern crunk to the mainstream remains unequivocal. — NEENA ROUHANI

They only recorded together for four years, but Mount Vernon, New York’s Pete Rock & CL Smooth left an indelible imprint on ’90s hip-hop. Rock’s mix of tight drums and inspired funk, R&B and jazz crate-digging made his production style one of the standard-bearers for East Coast rap. That combined with CL’s dexterous, commanding and soulful flows made sets like breakout 1991 EP All Souled Out and all-killer 1992 debut LP Mecca and Soul Brother among the most essential listens of their era. The duo’s signature song remains an absolute all-timer: “They Reminisce Over You (T.R.O.Y.),” an impossibly poignant, smiling-through-the-tears elegy for late Heavy D & The Boyz dancer “Trouble T. Roy” Dixon — raised to the heavens by the greatest sax loop in rap history. — ANDREW UNTERBERGER

Who knew that wearing clothes backwards could ever become a thing? It did in 1992 when Atlanta duo Kris Kross bounced onto the scene with the effervescent “Jump.” Its eight-week stand atop the Hot 100 — the first rap record to reign for that long — coupled with its success around the globe made for an early portent of hip-hop’s current worldwide popularity. Discovered by producer Jermaine Dupri and signed to Ruffhouse/Columbia, young teens and best friends Chris “Mac Daddy” Kelly (who died in 2013) and Chris “Daddy Mac” Smith turned their switched-around nicknames into a fashion statement that millions of fans eagerly adopted. In addition to “Jump,” Kris Kross’s short but estimable run through 1996 included crossover hits “Warm It Up” and “Tonite’s Tha Night” and platinum albums Totally Krossed Out and Da Bomb — helping pave the way for Bow Wow and other young rap stars. — GAIL MITCHELL

“The Kid’s much more than hair and a smile” raps the hi-top fade-rocking half of Kid ‘N Play in 1990’s surprise hit film House Party. Even if skeptics saw the party-rap duo as too safe and friendly at a time when gangsta rappers were firing shots heard ‘round the world, the NYC duo’s impact on culture was undeniable. House Party (the first in the film series) set the template for rappers eyeing the silver screen, while their easygoing flow and relatable raps on lightly funky classics like “Rollin’ With Kid ‘N Play” and Hot Rap Songs No. 1s “Ain’t Gonna Hurt Nobody” and “Funhouse” influenced future crossover success stories like Flo Rida and The Black Eyed Peas. Plus, in the late ‘80s and early ‘90s, few (if any) rappers could boast a buzzier fashion aesthetic. — JOE LYNCH

Rapper Dwight “Heavy D” Myers & The Boyz (dancers/hype men Glen “G. Whiz” Parrish and Troy “Trouble T. Roy” Dixon; in-house producer Edward “DJ Eddie F” Ferrell) was another ‘90s hip-hop group — the first signed to Uptown, future home of Notorious B.I.G. and Mary J. Blige — that percolated on uplifting, feel-good party vibes and smooth dance moves. After Heavy’s guest feature on hit singles by Levert (“Just Coolin’”) and Janet Jackson (“Alright”) in 1989, the rapper (also Pete Rock’s cousin) and his crew definitively proved “We Got Our Own Thang” that same year, with their first top 5 rap hit. The gentle giant — who died in 2011 — put his melodic flow and signature diddly-dee vocal riffs to good use on more party classics including “Somebody for Me,” “Got Me Waiting” and the R&B/pop crossover “Now That We Found Love.” — G.M. 

North Carolina fixtures 9th Wonder, Phonte and Big Pooh lassoed the competition when they formed Little Brother in the early 2000s. The triumvirate boasted formidable wordsmiths in ‘Te and Pooh and a burgeoning producer in 9th, who earned his breakout moment when he produced Jay-Z’s 2003 The Black Album standout “Threat.” LB’s first two albums, 2003’s The Listening and 2005’s The Minstrel Show, won over a cult fanbase with lush production, scintillating skits and lyrical landmines planted by the group’s cerebral MCs, notably on “Lovin’ It” and “Speed.” Though 9th Wonder left before the group’s third album, 2009’s Getback, ‘Te and Pooh’s unrelenting hunger remained intact through three more projects, including their 2019 gem May the Lord Watch. — C.L. 

Onyx’s penchant for sheer aggression and grimy raps made the group — spearheaded by Fredro Starr, Sticky Fingaz, Big DS and Suave — an indomitable four-headed monster in the early ’90s. Signed by Run-DMC’s legendary DJ Jam Master Jay, the quartet hit the ground running with 1993 debut album Bacdafucup, powered by the rowdy Hot 100 top five smash “Slam.” Relishing stage dives and body slams in their live performance, the group’s raging solidarity – they all donned shaved heads – also gave New York rap an extra edge at a time when Wu-Tang Clan, Mobb Deep and A Tribe Called Quest began etching their paths as perennial mainstays. — C.L. 

Slum Village breathed life into the Midwest rap scene when it bubbled up in the 2000s with soul-grabbing lyrics and funky samples. Originally comprised of venerated beat maestro J. Dilla alongside rappers T-3 and Baatin, Slum Village rose within Detroit’s rap ranks following 2002’s Trinity (Past, Present, and Future) and 2004’s Detroit Deli (A Taste of Detroit). Unfortunately, Dilla, who exited the group in 2001 to pursue a solo career, died in 2006, while Baatin passed away three years later. However, the group still marched forward, after recruiting Elzhi, one of rap’s heralded rhymers, to join co-founder T-3 and Dilla’s younger brother IIIa J. The group’s notable later-era releases include 2010’s Villa Manifesto and 2015’s Yes!  — C.L. 

Cash Money co-founder Bryan “Birdman” Williams and the label’s former resident producer Mannie Fresh were also partnered in another impactful endeavor: Big Tymers. Hailing from New Orleans, the Big Tymers stepped onto the scene with 1997 debut album How You Luv That. But with the release of 2000 sophomore platinum set I Got That Work, the duo’s undeniable musical chemistry ignited massive hits — “#1 Stunna” featuring Juvenile and Lil Wayne, plus “Get Your Roll On” — that further entrenched their hometown’s distinct southern flavor within the rap mainstream. The Big Tymers scored a Billboard 200 chart-topper and a second platinum album in 2002 with Hood Rich, featuring the proud-to-be-broke anthem “Still Fly,” and released Big Money Heavyweight before parting ways in 2005. — N.R.

Before the emergence of OutKast, Goodie Mob, Three 6 Mafia or Cash Money Records, there was 8Ball & MJG. The influential Memphis duo was among the originators and cornerstones of southern hip-hop, with arguably only the Geto Boys proving as influential in the first half of the ‘90s. Their 1993 debut, Comin’ Out Hard, is an early classic of the region. But it wasn’t just that 8Ball & MJG was early, the pair was also inarguably great — both collectively and on their own — at the craft of rapping. Their longevity and influence were such that it wasn’t until 2005, when they joined fellow Tennessee group Three 6 Mafia for “Stay Fly,” that they reached their peak chart success. But almost every Southern rapper of the last 30 years is in their debt. — D.R.

“Rap ain’t about bustin’ caps and f–king b–ches / It’s about fluency with rhyming ingenuity,” rhymes Del the Funky Homosapien on Hieroglyphics’ spiky 3^rd Eye Vision highlight, “At the Helm.” That was a pointed statement in the gangsta rap–dominated landscape of 1998. Coming after Del and his Oakland, Calif., associates in Souls of Mischief found themselves dropped from their labels — despite releasing some of the most lyrically dexterous, musically adventurous and acclaimed hip-hop albums of the ‘90s — it might as well have been their manifesto. Forming their own label, Hieroglyphics Imperium, the Hieroglyphics collective became as much a group as it was a way of life for the devoted underground following the group fostered via touring and Internet fan engagement in the pre-social media era. — J. Lynch

When The Pharcyde released debut album Bizarre Ride II The Pharcyde in 1992, hip-hop hadn’t seen anything like it. The hilariously garrulous quartet of South Central Angelenos spun wild, cartoonish tales over jazzy live instrumentation, brittle funk drum breaks and turntable scratches. Trading NSFW, puerile insults (“Ya Mama”) one moment while offering wry social commentary the next (the diaristic account of racist cops on “Officer”; a discourse on hip-hop sellouts and phonies on “It’s J-ggaboo Time”), The Pharcyde came across like the wittiest smart-assess on the West Coast, if not America. The vibey, loquacious “Passin’ Me By” landed on the Hot 100, and follow-up LP Labcabincalifornia gave them two more Hot 100 hits. But the group’s real impact was through serving as a low-key, persistent Holy Grail for ensuing generations of rappers unafraid to think – and laugh – outside the box.  — J. Lynch 

 
Though the group came up as part of a rising wave of alternative hip-hop at the turn of the ’90s, Brand Nubian never totally fit into the DAISY Age, with their flavor of conscious hip-hop rooted in a more sober social reality. (Member Sadat X’s version of said reality would later veer into outspoken prejudice, as unfortunately presaged in the homophobia of the group’s otherwise standard-bearing 1992 hit “Punks Jump Up to Get Beat Down.”) Still, Brand Nubian’s early output was sensational in more positive ways than controversial ones, with classic 1990 debut album One for All in particular a mostly glorious melding of vibrant samples, thoughtful rhymes, keen pop instincts and a united energy befitting its title. — A.U.

A quartet of ATLiens connected with producers Organized Noize and the larger Dungeon Family collective, Goodie Mob ran deeper and a little darker than their chart-topping compatriots in OutKast. Though Goodie Mob’s own crossover impact was a little more limited, they still scored three consecutive acclaimed (and RIAA gold-certified) ’90s albums in 1995’s Soul Food, 1998’s Still Standing and 1999’s World Party, while also notching two of the most unshakeable hits in southern hip-hop history with the tiptoeing menace of “Cell Therapy” and the stark soulfulness of “Black Ice (Sky High).” And with the higher-register rasp of Cee Lo Green, the group produced a breakout star who’d ultimately become one of the most prolific and versatile left-field pop artists of the early 21st century. — A.U. 

2 Live Crew courted major success — and controversy — when the Miami bass group unapologetically brought “nasty” to the mainstream in the late ‘80s. Then comprised of Luther “Luke” Campbell, Fresh Kid Ice, Mr. Mixx and Brother Marquis, the foursome first gained major attention with 1986 gold debut The 2 Live Crew Is What We Are, which featured titillating yet raunchy anthems like “Throw the D” and “We Want Some P—y.” Channeling more big-booty odes laced with uptempo, infectious beats and X-rated videos, the Crew’s 1989 third outing As Nasty as They Wanna Be pushed the boundaries of misogyny and sexual explicitness even further with hit single “Me So Horny.” In addition to going platinum, the album reached another pinnacle as well when it was declared legally obscene by the U.S. District Court in Florida. — NEFERTITI AUSTIN 

Founded by genre trailblazers KRS-One and DJ Scott La Rock, with a collaborator lineup that included producer Lee Smith, DJ D-Nice and Ced Gee of the Ultramagnetic MC’s, this seminal group mapped an early blueprint for diss tracks (“The Bridge is Over”) and also pioneered the fusion of dancehall reggae and hip-hop (“9mm Goes Bang”) on their 1987 debut, Criminal Minded. LaRock’s murder six months later inspired KRS to deliver social commentary instead of gangsta rap street stories, and to also form the Stop the Violence Movement supergroup, which released the 1988 No. 1 rap hit “Self Destruction.” Subsequent albums, including that same year’s By Any Means Necessary, 1989’s Ghetto Music and 1990’s Edutainment, each went gold. — RAQUELLE HARRIS 

The summer of 2002 was scorching, courtesy of Pharrell and his latest DMV partners, The Clipse. Though the duo came out in the ’90s, it wasn’t until 2002 when Virginia natives Pusha T and his brother No Malice (formerly Malice), shook the rap landscape with their thunderous anthem “Grindin’.” Doused with cocaine bars that made every corner boy smile, “Grindin” impacted cities from “ghetto to ghetto” and “backyard to yard” while having every middle school kid in America remake the classic Neptunes beat on lunch tables. Beyond “Grindin’,” the Thornton brothers’ dexterity and flash made their debut album (2002’s Lord Willin‘) a beloved smash, while its grimier follow-up (2006’s Hell Hath No Fury) became one of the decade’s most acclaimed rap albums. — C.L.

Rapper-producer duos rarely come with such high-quality, distinctive styles as Gang Starr. The Boston-Houston-Brooklyn connection of DJ Premier and Guru combined jazz-hop production with stylized street tales to create some of the most intricate hip-hop the world had yet seen when they burst out of the late 1980s and early 1990s. Premier is now rightly regarded as one of the greatest producers of all time, but it was his work with Guru that arguably got the best out of both of them, with the best evidence coming through the career-defining Step In the Arena (1991) and the influential Hard to Earn (1994). – D.R. 

Simply put, the Geto Boys put Texas, and the South as a whole, on the map. Propelled by the group’s most consistent lineup — Scarface, Willie D and Bushwick Bill — they were innovators and trailblazers, the ones who introduced the world to Rap-A-Lot Records and the gangsta rap lyricism of Houston and paved the way for other Southern groups to follow. And the group’s signature song, their 1991 crossover hit “Mind Playing Tricks on Me,” remains one of the darkest, most vividly intense hip-hop songs of the past four decades. – D.R. 

In West Philadelphia born and raised, disc jockey Jeff Townes and rapper Will Smith (known as DJ Jazzy Jeff & The Fresh Prince) softened hip-hop’s rough edges with lighthearted, narrative raps and dynamic turntablism — and, in doing so, made the genre fully accessible to mainstream audiences. Smith later became a household name when he starred in his own sitcom The Fresh Prince of Bel-Air, for which he and Townes (who had a recurring role) recorded the iconic theme song. DJ Jazzy Jeff & The Fresh Prince were ultimately responsible for several milestone moments in hip-hop, from releasing the first double album in the genre with 1988’s He’s the DJ, I’m the Rapper to earning the first-ever Grammy for best rap performance in 1989, with their breakout story song “Parents Just Don’t Understand.” — H.M.

 
Straight outta Brentwood, N.Y., Erick Sermon and Parrish Smith teamed up as EPMD in the late ‘80s, two concrete-hard MCs who never suffered fools. They set a new template for the genre with their slow-cooked, deliberate flows, which carefully brought the hammer down on key syllables. Their minimalist DIY production proved wildly prescient: the duo bounced atop funk grooves well before G-funk’s commercial ascent, and delivered winking tweaks on pop radio hits well before Diddy. Their 1988 debut Strictly Business remains an ageless, unimpugnable classic; your mileage may vary on follow-up albums (all with “business” in the title) But 1992’s Business Never Personal is a brittle, uncompromising LP that produced their highest-charting track, “Crossover” (No. 42 on the Hot 100); ironically, it’s a testy takedown of rappers chasing mainstream success by dabbling in pop or R&B. — J. Lynch

The late-‘90s southern rap renaissance conversation isn’t complete without paying homage to the Hot Boys. Their 1999 sophomore album, Guerrilla Warfare, peaked at No. 1 on the Billboard Top R&B/Hip-Hop Albums chart, catapulting the group – made up of Juvenile, Turk, B.G., and a 15-year-old Lil Wayne – into mainstream recognition. But before then, their debut independent set Get It How U Live! via Cash Money Records dominated locally, selling 400,000 copies and establishing the trio’s undeniable chemistry. Although the group disbanded in 2001, only four years following their formation, the influence of their sound (and the later success of Lil Wayne and Juvenile as solo stars) changed the trajectory of rap music forever. — N.R.

Harlem’s superteam of Cam’ron, Jim Juelz, Juelz Santana, and Freaky Zeeky wreaked havoc on the hip-hop game when they assembled to form The Diplomats in the early 2000s. Oozing with swagger, the East Coast version of the Four Horsemen trampled adversaries when they gathered on 2003’s Diplomatic Immunity. Powered by high-octane production from Just Blaze and The Heatmakerz, the Dipset crew doled out hood classics such as “I Really Mean It,” “Dipset Anthem” and “Real N—as,” and further cemented their grip on East Coast rap when they unleashed their sequel Diplomatic Immunity 2 the following year. — C.L. 

Others were more influential, but maybe only Run-D.M.C. were more impactful among groups of hip-hop’s first 15 years than the Sugarhill Gang. “Rapper’s Delight” wasn’t technically the first hip-hop record, but it was the first most suburban Americans ever heard, and the first to cross over to the top 40, peaking at No. 36 on the Hot 100. With a disco groove borrowed from Chic’s “Good Times” (and some lyrics controversially swiped from Grandmaster Caz of the Cold Crush Brothers), the instant classic remains one of the most important and enduring records in American popular music, spawning countless quotes and mini-catchphrases that are still part of hip-hop’s shared language today. And while it remains the group’s signature song, subsequent hits “Apache” and “8th Wonder” were also iconic early-’80s party-starters, sampled and referenced for decades to come. — A.U.

Childhood friends Sheek Louch, Jadakiss and Styles P, were known for not only their cunning cadence and complementary craftsmanship, but brushing their own swagger on jams from pop titans J. Lo and Mariah Carey. They initially captured the spotlight on projects like Biggie’s Life After Death, Puff Daddy’s No Way Out and Ma$e’s Harlem World in 1997, before “Money, Power & Respect” — the Lil Kim- and DMX-featuring title anthem to their 1998 debut album — became a culture-shaping mentality. After parting ways with Bad Boy to join Ruff Ryders in 1999, the next year’s We Are the Streets brought gritty gems with “Ryde or Die, B–ch” (featuring Timbaland and Eve) and “Wild Out.” Their legacy was further cemented with a triumphant run against The Diplomats during their 2021 Verzuz, and a headline-making homecoming performance this June at Summer Jam 2023. — R.H.

Putting Cleveland on the hip-hop map, crooners and rhymers Bone Thugs-N-Harmony — comprised of Bizzy Bone, Wish Bone, Layzie Bone, Krayzie Bone and Flesh-n-Bone — first caught the ear of N.W.A’s Eazy-E in 1993. The quartet signed to Ruthless Records that year and enjoyed major breakouts with debut EP Creepin on ah Come Up in 1994 and first full-length E. 1999 Eternal in 1995. For over a decade, their unique style of gospel melodies, cinematic beats and a staccato lyrical flow made them a regular presence on the Hot 100, including the chart-topping “Tha Crossroads,” which spent eight weeks at No. 1 and earned the group their first Grammy. — N.A.

The duo, comprised of Bun B and Pimp C, may not have been the first great Houston rap group, but they came to define the city’s trunk-rattling grit with albums like 1996’s classic Ridin’ Dirty. The Underground Kings finally got their mainstream due by collaborating with Jay-Z on his crossover smash “Big Pimpin’” in 1999 (as well as Three 6 Mafia’s “Sippin’ on Some Syrup” the following year). Their greatest collab would come in 2007 with the OutKast-assisted “Int’l Players Anthem (I Choose You),” before Pimp C tragically died at age 33 from an overdose later that year. The duo’s influence extends even further than their output; artists from Kendrick Lamar to A$AP Rocky to Megan Thee Stallion regularly invoke their style, while Bun has become one of the true elder statesmen of the game. — D.R. 

In some ways, the history of hip-hop can be seen through two lenses: the era before G-Unit and the era after. Led by 50 Cent, the crew’s classic core (50, Lloyd Banks, Tony Yayo and Young Buck) took the world by storm, utilizing an endless flow of mixtapes, beefs and cold, hard lyricism to effectively put the rap game in a chokehold from 2002 to 2007. Infighting — and changing times in hip-hop — ultimately led to the group’s undoing. But there are few true crew albums that can stand alongside 2003’s Beg for Mercy in terms of unfiltered, sneering bangers, with earworm hooks and verses dripping with braggadocio. At its height, the crew was everywhere: MTV, the charts, Reebok sneakers, G-Unit clothing lines and relentless street marketing campaigns that left no oxygen remaining for anyone else who tried to claim some of their rarified air. New York City — and hip-hop in general — has never been the same since. — D.R. 

One of the all-time cult hip-hop groups, Three 6 Mafia sprouted from early-‘90s Memphis and proceeded to spend the next two decades tearing the club up. Three 6 captivated at their turn-of-the-century peak with raunchy, aggro floor-fillers built around thunderous bellowing from MCs Gangsta Boo, Crunchy Black, Koopsta Knicca, Lord Infamous, DJ Paul and Juicy J – the latter two members also providing the group’s imposing, darkly cinematic beats. After setting the table for crunk’s early-‘00s takeover (and now back down to the trio of DJ Paul, Juicy J and Crunchy Black), they scored their biggest crossover smash alongside kindred spirits 8Ball & MJG with 2005’s stoner classic “Stay Fly,” and then made Oscar history the next year with their Hustle & Flow anthem “It’s Hard Out Here for a Pimp.” Sadly, all three of the group’s former members would die in their early 40s: Lord Infamous in 2013, Koopsta Knicca in 2015 and Gangsta Boo in 2023. – A.U. 

Cypress Hill took hip-hop higher on their self-titled 1991 debut, with the mind-bending boast tracks “How I Could Just Kill a Man” and “Hand on the Pump.” DJ Muggs’ inventive, pulsating production accentuated B-Real’s frenetic timbre and Sen-Dog’s grimy register as they promoted love for and legalization of cheeba long before cannabis became legal. Their bilingual lyricism broke barriers when 1993’s Black Sunday debuted at No. 1 on the Billboard 200, featuring adrenalized hits like “Insane the Brain,” “I Ain’t Goin’ Out Like That,” “Hits from the Bong,” and percussionist Eric Bobo’s addition in 1994 amped up the group’s energy quotient. Cypress Hill also became the first Latino rap group to receive a star on the Hollywood Walk of Fame.  — R.H. 

Throughout their many iterations — from the party-rap shout-alongs of Licensed to Ill to the sample pastiche of Paul’s Boutique; from the rap-rock action drama of “Sabotage” to the old-school wiggle of “Intergalactic” — Michael “Mike D” Diamond, Adam “MCA” Yauch and Adam “Ad-Rock” Horovitz loved two things: rapping and rapping alongside each other. These three Jewish white boys from New York City discovered a shared passion and unbreakable artistic bond in the mid-‘80s. Then they spent decades preserving their vision, squeezing out anthemic hooks between hilarious music videos and unforgettable industry pranks together, as their creativity, humor and love of their craft earned the respect of the hip-hop community. The tragic 2012 passing of Yauch effectively ended the Beastie Boys, an iconic group unthinkable as anything but a trio. — J. Lipshutz 

 
When Naughty by Nature dropped its self-titled debut in 1991, members Treach, Vin Rock and DJ Kay Gee blazed a trail on which Biggie and ‘Pac would soon run marathons. Balancing an album of hard, menacing raps (“Uptown Anthem,” “Yoke the Joker”) with an irresistibly hooky single (the mischievous Jackson 5-sampling cheating celebration, “O.P.P.”), the East Coast MCs scored a No. 6 Hot 100 crossover hit without sacrificing street cred. Follow-up album NineteenNaughtyIII found the trio as tough as ever — Treach wields a frickin’ chainsaw on the cover art — while also producing one of hip-hop’s all-time sing-along classics, the funky and summery “Hip Hop Hooray.” Becoming another top 10 hit on the Hot 100, the track demonstrated that respected rappers could soar on the radio and still flaunt serpentine flows and clever wordplay.  — J. Lynch 

The Fugees breakout stands out as a momentous chapter in the genre’s history. Members Wyclef Jean, Pras Michel and a then-15-year-old Lauryn Hill contributed to the diversification of Black identity in popular culture through potent rhymes that were equal parts conscious and commercially relevant. Deriving the group name from the word “refugee” — a term often weaponized against immigrants from numerous countries (including Wyclef and Pras’ native Haiti) — the trio reclaimed the word, while creating music that countered the growing gangsta rap of the mid-‘90s. Multi-platinum-certified sophomore effort The Score proved the power of their authenticity: Recorded in Jean’s uncle’s basement, the Grammy-winning album featured the timeless hits “Killing Me Softly” and “Ready or Not.” Despite only releasing two albums, the Fugees became one of the best-selling hip-hop groups of all time. — N.R.

Death Row’s triumvirate of 2Pac, Dr. Dre and Snoop Dogg held the rap game in a Cobra clutch in 1994. The West Coast movement wreaked terror on the Billboard charts and the streets, to the dismay of their East Coast rivals. But Queens duo Mobb Deep upped their odds with the magnum opus “Shook Ones (Pt II).” The ominous heater evoked a certain edge and aggression that the East Coast lacked at the time. Prodigy’s 24 bars of fury became the gold standard for mid-’90s lyricism as he and Havoc dished out more indelible bars on debut album The Infamous, including such stellar tracks as “Give Up the Goods” and “Survival of the Fittest.” The duo’s chemistry remained unmatched when they tangoed on 1999’s Murda Muzik, highlighted by the club scorcher “Quiet Storm” (elevated by Brooklyn fireball Lil Kim appearing on the remix). Despite Prodigy’s untimely passing in 2017, his and Havoc’s legacy as prime-time rhymers is well-documented and well-remembered, also thanks to deeper classics like “Win or Lose,” “The Realest” and “Hell on Earth.” — C.L.

When the late ‘70s ushered in rap, Grandmaster Flash and the Furious 5 was among the genre’s early trailblazers founded in the South Bronx by the namesake DJ/producer, with a five-member crew of Melle Mel, Kidd Creole, Keef Cowboy, Scorpio and Rahiem. Grandmaster Flash manipulated the turntable with magical fingers that made vinyl talk, between cutting, scratching and back-spinning, while Melle Mel crafted social commentary about ghetto life. Signing in 1980 with Sugar Hill Records, the group first attracted national attention with “Freedom.” But with 1982’s signature hit “The Message” and 1983’s “White Lines (Don’t Don’t Do It)” the group brought social commentary to the forefront, influencing future conscious practitioners such as Public Enemy and KRS-One. Grandmaster Flash and the Furious Five went on to become the first hip-hop group inducted into the Rock & Roll Hall of Fame in 2007. — N.A. 

The culture-shifting trio from Atlanta changed the rap game forever with their rapid-fire triplet flow (nicknamed the “Migos flow”), memorable ad-libs and intricately layered trap production. Their 2013 breakout hit “Versace” showcased their infectious energy (which instantly lured Drake to its remix) and also set the stage for Migos’ chart-topping success, via their first Hot 100 No. 1 in 2017 with “Bad and Boujee.” Throughout their trilogy of Culture albums, Migos maximized all three members’ strengths – Quavo’s auto-tuned melodic hooks, Offset’s raw rags-to-riches narratives and Takeoff’s underrated consistency as the group’s best rapper – to create a mesmerizing sound that redefined rap, also thanks in part to go-to producers like DJ Durel, Zaytoven and Murda Beatz. Even after Takeoff’s untimely shooting death in 2022, Migos will always be remembered for shaking up the culture while staying true to their roots. — H.M.

The brainchild of Tariq “Black Thought” Trotter and Ahmir “Questlove” Thompson, both teenagers at the time of the group’s inception, The Roots achieved unprecedented success for a full band in hip-hop. Throughout all its member iterations, the group remained an authority in the experimental space, capturing the essence of what Black Thought called “organic hip-hop jazz” and delivering some of the genre’s most iconic moments. Their 2000 cut “You Got Me,” alongside Erykah Badu and Eve, took home the Grammy for best rap performance by a duo or group, while their 1995 debut album Do You Want More?!!!??! remains a genre classic. The Roots proved influential outside of their own catalog as well, accompanying Jay-Z during his famous MTV unplugged acoustic set and collaborating with R&B greats including D’Angelo, Jill Scott, Musiq Soulchild and others. Lyrically, Black Thought and the late Malik B. matched the group’s awe-inspiring instrumentation, fusing conscious themes with impressive rhyme schemes that captured listeners’ attention across generations and demographics. — N.R. 

With the release of 3 Feet and Higher in 1989, De La Soul (Posdnous, Trugoy the Dove and Maseo) dished up a game-changing debut album whose puckish rhymes and skillful sampling shifted hip-hop away from violence and materialism towards peace, love and having fun. The album also spawned the trio’s biggest hit with the delirious Hot 100 crossover smash “Me, Myself and I.” De La Soul further solidified its principal role in the evolution of jazz rap and alternative hip-hop through a series of albums — 1991’s De La Soul Is Dead, 1993’s Buhloone Mindstate, 1996’s Stakes Is High, 2000’s Art Official Intelligence: Mosaic Thump and 2001’s AOI: Bionix — while also moving beyond the “DAISY Age” trappings of their debut. Innovative sampling was also a De La Soul hallmark, with the group selecting beats from a diverse menu that included Parliament-Funkadelic, Johnny Cash and Bob Marley and The Wailers — though that edge also mired the group in litigation for decades. De La Soul went on to earn a Grammy in 2006 for best pop collaboration for “Feel Good Inc.” with Gorillaz. Sadly, Trugoy died in February 2023 — just weeks before De La Soul’s enduring catalogue finally hit streaming channels. — N.A.

Salt-N-Pepa led the charge for female empowerment when it came to commanding respect in a male-dominated industry back in the ‘80s. The pioneering trio — Cheryl “Salt” James, Sandra “Pepa” Denton and Deidra “DJ Spinderella” Roper — shook up the industry with 1985’s “The Showstopper,” a dismissive response to Doug E. and Slick Rick’s “The Show.” The track was featured on their 1986 debut album, Hot, Cool & Vicious, along with perpetual party anthem and top 20 Hot 100 hit “Push It.” Coming into their own creatively while living authentically as Black women took center stage on 1990 third album Blacks’ Magic, which included the exhilarating “Expression,” the melodic “Independent” and the socially conscious “Let’s Talk About Sex.” Platinum was struck with 1993 fourth album Very Necessary, which spun off the lustful “Shoop,” the celebratory “Whatta Man” (featuring En Vogue) and the daring “None of Your Business,” which won the trio the Grammy for best rap performance by a duo or group. Between their savvy beats, unapologetic lyrics and sexy fashion sense, Salt-N-Pepa singlehandedly changed the sound and look of hip hop. — R.H.

 
Still the prototypical DJ/rapper duo for many fans, Eric B. & Rakim magnetized the hip-hop world from the opening lines of their very first single, 1986’s “Eric B Is President.” The Long Island pair followed that iconic entrance with one of the greatest debut albums from any genre: 1987’s Paid in Full, which combined Eric B’s otherworldly ear for supercharged funk and jazz samples (and inspired scratches) with the voice-of-God delivery of Rakim, whose singular steeliness and Shakespearean aptitude for quotable and adaptable rhymes gave him an authority no one from hip-hop’s first decade of shouters could match. Beloved follow-up Follow the Leader (1988) was a similarly essential document of hip-hop’s golden age, while final album Don’t Sweat the Technique (1992) and its Juice-soundtracking single “Know the Ledge” proved they could stay vital into the ‘90s – though financial and legal disputes sadly led to the duo’s dissolution the following year. — A.U.

Long Island, NY’s Public Enemy is the rare musical act that could not only intelligently respond to the times, but also completely embody every emotion and mood that shapes a given sociopolitical period. With groundbreaking albums like Yo! Bum Rush the Show (1987), It Takes a Nation of Millions to Hold Us Back (1988) and Fear of a Black Planet (1990), PE — whose original members were Chuck D, Flavor Flav, Professor Griff and Terminator X — pioneered some of the most visceral and nuanced political commentary in hip-hop. Their innovative use of samples and fearless embrace of radical Black politics presented a group that was as committed to revolution and liberation as they were to storytelling and world-building.

From “911 Is a Joke,” their scathing takedown of intentional police laziness, to seminal protest anthem “Fight the Power,” Public Enemy didn’t just critique the action: They were directly involved in the fight for a brighter, Blacker future. Public Enemy kicked off this young decade by accepting the Grammy Lifetime Achievement Award, an indelible honor that doesn’t even begin to capture the breadth of their impact and influence. Then again, no trophy could. — KYLE DENIS

Jason “Jam Master Jay” Mizell, Joseph “Run” Simmons and Darryl “DMC” McDaniels pioneered hardcore East Coast hip-hop in the ‘80s by fusing rap and rock., helping push the genre into the mainstream during a period since tagged as the golden age of hip-hop. As their spare beats, socially conscious lyrics and aggressive delivery captured the spirit of the streets and shifted away from hip-hop’s disco- and funk-rooted sound, Run-D.M.C.’s genre-bending sonics – demonstrated by their groundbreaking “Walk This Way” collaboration with Aerosmith – broke racial and musical barriers. The group also revolutionized the aesthetics of hip-hop culture by introducing the street B-Boy style: Kangol hats, Adidas tracksuits and laceless sneakers. Run-D.M.C. paved the way for rap to dominate pop cultural spaces it had never entered before by becoming the first rap group to receive a Grammy nomination, score a platinum-certified album (with Raising Hell), get their music video aired on MTV (with “Rock Box”), sign a major endorsement deal (with Adidas) and be presented the Grammy Lifetime Achievement Award (in 2016), among countless other accolades. Sadly, Mizell was murdered in 2002. — H.M. 

Beginning its recording career on 1989’s “Native Tongue Decision” remix of “Buddy” by De La Soul, A Tribe Called Quest came out the gate with three unimpugnable classics — 1990’s People’s Instinctive Travels and the Paths of Rhythm, 1991’s The Low End Theory and 1993’s Midnight Marauders — which served as warmly glowing guideposts for a generation of rappers more concerned with self-expression than commerce.  Q-Tip, Phife Dawg, Ali Shaheed Muhammad and on-and-off member Jarobi White could wax philosophical (“Sucka N—a”), spin a silly yarn (“I Left My Wallet in El Segundo”) and get brainy while boasting (“Scenario”) without breaking a sweat. From day one up to their 2016 reunion swan song We Got It From Here… Thank You 4 Your Service (released shortly after Phife’s death at age 45), Tribe’s ganja-tinged grooves and conversational flows could relax the body while energizing the mind. A group that inspired countless artists but were equaled by none, you simply can’t understand the last three decades of rap or alternative music without an ATCQ immersion.  — J. Lynch

On the way to becoming the rap legends they are now, Ice Cube, Dr. Dre, and Eazy-E first began their quests as members of one of the most dominant groups of all-time, N.W.A. Originally comprised of Cube, Dre, Eazy, MC Ren, Arabian Prince, and DJ Yella, the California faction began in 1987 with the release of compilation album N.W.A and the Posse. Arabian left the group the following year, before their seminal debut album, Straight Outta Compton, dropped. Under Jerry Heller’s Ruthless Records banner, the quintet ushered in a new gangsta rap era that ruminated on the harrowing experiences of Black men in Compton. While “Straight Outta Compton” had the rap game in shambles, it was follow-up single “F–k tha Police” that drove shivers down the nation’s spine, ringing incessantly in every hood before the FBI wrote a letter decrying the track’s messaging — further bolstering N.W.A’s claim as rap’s most dangerous group. Though N.W.A disbanded after its second and final studio album N—az4Life — Cube left in 1989, and Dre departed in 1991 — the group’s legacy remains enshrined in American culture, following its induction into the Rock and Roll Hall of Fame in 2016 and its anthologizing in the smash 2015 biopic film Straight Outta Compton. — C.L.

“Wu-Tang again?” “Ah, yeah, again and again!” Never has a group before or since burst onto the scene with such unbridled power, self-assurance, bravado and top-level lyricism than the nine-headed monster that is the Wu-Tang Clan — thanks to 1993 debut album Enter the Wu-Tang (36 Chambers) and its bombastic, gritty lead single “Protect Ya Neck.” In a hip-hop world dominated by the G-Funk of Dr. Dre’s West Coast, the Wu reoriented the landscape through a deep love of martial arts movies, RZA’s minimalist soul beats and some of the most innovative MCs that hip-hop has ever seen. To quote GZA at the beginning of “Method Man”: “From the slums of Shaolin, Wu-Tang Clan strikes again/ The RZA, the GZA, Ol’ Dirty Bastard/ Inspectah Deck Raekwon the Chef/ U-God, Ghostface Killah and the METHOD Man,” with Masta Killa and later Cappadonna. The group revolutionized not just how hip-hop sounded, but how its business was handled — like RZA cutting a groundbreaking deal to allow each of the crew’s MCs to sign individual solo pacts with any label they wished. And while several of those solo albums are certified classics, the Wu-Tang Clan was always better when they banded together like Voltron and came for necks. — D.R.

 
“Nothing is for sure, nothing is for certain/ And nothing lasts forever, but until they close the curtain/ It’s him and I, Aquemini.” When André 3000 rapped that declaration on 1998’s “Aquemini,” he and Big Boi had already established an indelible sound and persona as OutKast, released a treasure trove of mind-bending Southern rap and helped establish Atlanta as a central hub in hip-hop. The immediate future was unexpected — a crossover explosion at the turn of the century, crystallized by No. 1 singles like “Ms. Jackson” and “Hey Ya!” and an album of the year Grammy win for 2003’s double-LP opus Speakerboxxx/The Love Below — and indeed, the reign would not last forever, with 2006’s Idlewild ostensibly marking the end of the pair’s studio output. Yet André Benjamin and Antwan Patton, teenage pals in early-‘90s Atlanta who imagined upending hip-hop together, will forever be linked; their creative luminescence and commercial impact as inseparable as an Aquarius and Gemini forming an undeniable ionic bond. 

The greatness was always in the contrast: Big Boi the tough-spitting realist, André 3000 the outlandish philosopher. And those differences deepened over time, to the point where the two MCs inhabited separate worlds (while still topping charts) on Speakerboxxx/The Love Below. Yet OutKast’s run from 1994’s gloriously brash Southernplayalisticadillacmuzik to 2000’s wildly innovative Stankonia remains unparalleled — a duo of polar opposites united in the dream of expanding rap’s sonic boundaries, one classic album at a time. Although Big Boi and André have moved on to other projects and mostly circled out of each other’s creative lives, their legacies will always be intertwined; distinct voices echoing across the annals of hip-hop in perfect harmony. OutKast set the gold standard for rap groups. Maybe nothing lasts forever, but it sure feels like their legacy will. — J. Lipshutz