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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. — CARL LAMARRE 

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. — NEENA ROUHANI 

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. — DAN RYS 

“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.   — JOE 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.L. 

 
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. — ANDREW UNTERBERGER 

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. — CARL LAMARRE 

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). – DAN RYS 

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.” — HERAN MAMO 

 
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. — JOE 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. — NEENA ROUHANI 

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. — ANDREW UNTERBERGER 

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. — RAQUELLE HARRIS 

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. — NEFERTITI AUSTIN