The 100 Best East Coast Hip-Hop Songs of All Time

A powder keg (and a publicist’s nightmare), Azealia Banks held true to the technical fundamentals of rapping while separating herself from conventional New York hip-hop by fusing her music with house and electronic elements. “212”was different from anything else to gain traction in the blog era. Even though the song had no real hook, Bankscaptivated the masses by pivoting between rapping and singing with a series of unique accents that culminated with a repeated chaotically yelped refrain. A true one-of-one act, her dynamic personality bled through her music and into real life, for better or worse. —J.F.

Nobody was anywhere near Big Daddy Kane’s zone on the mic — a one-two punch of loverman charisma and virtuoso poetics. Antonio Hardy was born in Bed-Stuy but joined Marley Marl’s Juice Crew out in Queens, writing rhymes for his high school friend Biz Markie. But “Ain’t No Half Steppin’” is the wrath of Kane: He goes Friday the 13th on any rival MC fool enough to step to his throne, over Marl’s rump-shaker of a Stax soul sample. Only Kane could get so ill on his creative process: “Brain cells are lit, ideas start to hit/Next the formation of words that fit/At the table I sit making it legit / And when my pen hits the paper … aaaaw shiiit!” For golden age fiends, Kane will forever be the King Asiatic Nobody’s Equal. —R.S.

“Planet Rock” is a landmark collaboration by producer Arthur Baker; keyboardist John Robie; vocal troupe Planet Patrol; and the Soulsonic MCs Pow Wow, G.L.O.B.E., and Mr. Biggs. At its center is Afrika Bambaataa, the onetime Black Spades leader from the Bronx who evolved into the founder of the Zulu Nation and a DJ renowned as a “master of records.” His “Planet Rock” is not only hailed as the first electro-rap banger, but also as a representation of his curatorial taste: It interpolates snippets of Kraftwerk’s “Numbers” and “Trans-Europe Express,” all while the Soulsonic MCs engage in a unique staccato flow full of onomatopoeia. “Planet Rock” remains one of the most influential rap songs ever and virtually birthed the electro genre.Recent allegations against Bambaataathat have damaged his personal legacy can’t change that. —M.R.

Big Pun had been honing his agility as a rapper for roughly a decade before his commercial breakthrough, Capital Punishment, and its second single, “Still Not a Player.” The hit sprung from the confluence of his 1997 underground favorite “I’m Not a Player” and a similarly titled single by the R&B singer Joe that came out just months before. Pun floated over new production by Knobody (who also made Jay-Z’s “Can’t Knock the Hustle”), with its cheery piano loop pulled from Brenda Russel’s “A Little Bit of Love.” While Fat Joe, Pun’s friend and mentor, insists that he gave Pun the iconic, uncensored line “I’m not a player, I just fuck a lot,” it’s Pun’s nimble verses that are truly impressive. Pieces of “Still Not a Player” have been repurposed in songs by artists as disparate as Davido, Ariana Grande, and YoungBoy Never Broke Again, a testament to its solid place in the pop-rap canon. —M.C.

Even though A$AP Rocky’s “1 Train” is just an album cut from his debut album, Long.Live.A$AP, it remains one of his most famous songs. That’s not only due to the guests he gathered for this posse cut — Action Bronson, Big K.R.I.T., Danny Brown, Joey Bada$$, Kendrick Lamar, and Yelawolf, all from different regions in the U.S. — but also for the way it captures the increasingly online nature of East Coast hip-hop. Rocky’s A$AP crew specialized in blurring styles, from the slushy, “screwed” sound of Houston to the gauzy forms of Bay Area “cloud rap,” that drew favor on online platforms like Tumblr. “1 Train” has a boom-bap beat, yet it’s courtesy of California-raised producer Hit-Boy, and the song has a transnational flavor typical of rap in the early 2010s. At its center is the slyly charismatic A$AP Rocky, the future husband of Rihanna, leading NYC into a brave new era. —M.R.

One of the sharpest, most savage MCs of the golden era, MC Lyte slashed through hip-hop machismo on her relentless “Paper Thin,” a chorus-free dissection of a cheating partner. The rap had been chilling in her rhyme book since the early ’80s, back before she ever had a boyfriend, but the sentiment proved so relatable and the rhymes so timeless that it would end up remade by both Bahamadia and Missy Elliott. “Yeah, you know, Missy, every time we get a chance to really talk, she starts quoting lyrics of any of my songs,” Lyte told Rolling Stone. —C.W.

In 2002, Curtis “50 Cent” Jackson was more legend than star, a promising up-and-comer who had his debut album derailed after getting shot nine times. Surviving his brush with death — and emerging with a gravelly, slurred texture to his voice after catching a bullet with his left cheek — 50 Cent returned as New York’s new model for street mixtapes. His return single, “Wanksta,” was possibly a barely-veiled jab at fellow Queens rapper Ja Rule. The biting, sardonic lyrics — aimed to impugn the street credibility of fake gangsters — were delivered emotionless and with disregard, performed over a nursery-rhyme-style melody. “We put that shit on a mixtape.No Mercy, No Fear. Track 18,” producer Sha Money XL told Okayplayer. “It took off and then Eminem put it on the soundtrack to8 Mile. We were the first ones taking mixtapes and turning them into albums, breaking real artists.” —S.I.

The proudly feminist landmark “Ladies First” lays plain, in unambiguous terms, that women were always critical members of the hip-hop community. On the song, Newark’s Queen Latifah and London’s Monie Love demand equal acknowledgment for women’s prowess and proficiency in a way that’s righteous, defiant, and incredibly catchy. The video is a defiantly Afro-feminist history lesson that recenters women’s positions at the forefront of every major Black movement. “I’m gonna give it to Latifah and say that she had more cognizant intentions for that song than I did,” Monie Love told Talib Kweli. “I just wanted to rhyme. And I just wanted to shit on every dude.… I wanted to strike fear in the hearts of men in hip-hop, as far as what I sounded like on the mic.” —S.I.

In the annals of coke rap, few opening bars could contend with the illustrative, Moby Dick-sized allegory with which Jadakiss kicks off the first verse on this bona fide hustler’s anthem. In a deliberate departure from his earlier appearances via Bad Boy Records, the raspy Yonkers MC reveled in the decidedly grimier Ruff Ryders aesthetic for his solo debut. Over a triumphant beat by future production legend The Alchemist, he embodies tough talk and outsized ambition on this overt drug-dealer motivational. Trading off every few lines with Styles P, his more-than-capable cohort from The LOX, he conjures up King of New York references while essentially advertising his prowess as a kingpin. —G.S.

Everything else recorded by Beastie Boys after the Rick Rubin-produced Licensed to Ill technically qualifies as West Coast hip-hop. But nothing’s more Eighties NYC than sitting on a stoop outside a Gramercy recording studio nursing quarts of beer, Run-D.M.C. racing toward you screaming “Here’s a little story I got to tell!!!,” and recording a song that rap’s greatest group basically gifted you weeks later. This cowboy-themed origin story of Ad-Rock, MCA, and Mike D came inspired by the Sergio Leone spaghetti western Once Upon a Time in the West, its titular horse’s name taken from Guys and Dolls. But when MCA casually suggested, “Let’s just make a simple [Roland TR-808] drum pattern but flip the tape over and record the drum machine backwards,” heads were blown forevermore. —M.M.L.

There’s some disagreement about whether the irrepressible “Rapper’s Delight” was technically the first rap record on wax, but there’s no question that it was the first rap record the world ever heard, instantly repositioning the artform from New York underground expression to global phenomenon. A trio cobbled together in the parking lot of a pizza parlor by Sugar Hill Records CEO Sylvia Robinson, the Gang spit rhymes — both original and borrowed — for nearly 15 minutes. The world had heard nothing like it, and untold numbers of now-legendary MCs were instantly inspired to start writing rhymes. “People were waiting in stores for weeks upon weeks. We couldn’t sell the record fast enough; we couldn’t press it fast enough,” Joey Robinson of Sugar Hill Records said in Yes Yes Y’all: Oral History of Hip-Hop’s First Decade. “The radio would go on the air and say, ‘Stop calling … We’re going to play it at 7 o’clock’ … Just so the phone lines would be free, because so many calls were coming in on this record.” —C.W.

The streets-dominating cut from Raekwon’s classic solo debut, 1995’s Only Built 4 Cuban Linx, is a brashly uncompromising anthem — a veritable street-holler how-to for guys who have limited sexy-time moments between hand-to-hand coke sales. Neatly every line here resonates with gauche charm. When Method Man thunders, “Watch these rap niggas get all up in your guts,” after Ghostface Killah admits, “You can have anything in this world except C.R.E.A.M.,” the effect is both melodic and sweet — a gutter rendition of an ice-cream truck’s Pied Piper jingle. The result is the finest Wu Tang solo moment. —W.D.

Cam’ron did more for the color pink than Friz Freleng. When the high-pitch coo of “Oh Boy” rang off, it was like a siren call for the tall-white-tee-rocking set; almost instantly, they donned lavender in homage to Killa. That’s how serious Dipset’s movement was when Cam released this Just Blaze-produced banger. The swag, slang, and bop are quintessentially Harlem — all flash, flavor, and impossible charm. And Cam keeps the zingers as dense as a fall look book. “Clap at your soldiers sober, then leave after it’s over,” he sneers. Cam didn’t just popularize a pastel; he blessed us with sharply colorful bars. —W.D.

“It came out and within a day or two, people in the Tunnel knew every word,” DJ Cipha Sounds told Complex about how this Biggie single went over at the storied hip-hop club. “Flex played it for like 45 minutes straight. The last song released in Biggie’s lifetime played to all of his strengths: his technical dexterity, his pop star charisma, and his ability to rock clubs. The song’s trippy backbone was built off Herb Alpert’s 1979 Number One hit “Rise.” “Over the years I was approached by Ice Cube, Eazy-E, Vanilla Ice, and maybe another four to five artists to use the song and I never said yes until I heard a rough version of Biggie’s recording,” songwriter (and Herb’s nephew) Randy Alpert told Songfacts. [W]hen I cranked it up I not only immediately loved it, but my gut thought that this could be a Number One record once again.” Alpert’s instincts were correct, and “Hypnotize” became the second of four Bad Boy records to top the charts in 1997. —C.W.

The pulsing bass, hard drums, and wailing vocal sample on this classic 12-inch perfectly encapsulate the hopped-up aura of New York City in the late Eighties — a place where Wall Street bros sniffed coke off ill-earned Ben Franklins, and crack titans pushed Lambos up and down the blocks. Tapping into that mayhem, Rakim kicked knowledge that showed he could rise above the chaos. For the original’s historic remix, English electronic duo Coldcut sampled a Hebrew poem — Ofra Haza’s 1984 version of “Im Nin’alu” — to make this riveting tale of reinvention sound both worldly and enlightening. Clocking in at Number 65 on Billboard’s Hot R&B/Hip-Hop Songs, “Paid in Full (Seven Minutes of Madness)” was monumental; it introduced the self-styled “microphone fiend” to marquee nightclubs. —W.D.

Lil’ Kim charged out the gate on the blush-inducing “Big Momma Thang” pontificating on the joys of oral sex, shouting out porn stars, bragging about owning land in Switzerland, and turning down marriage proposals. Today Queen Bee’s culture-shifting influence among the current movement of empowered female rappers from Megan Thee Stallion to the City Girls is omnipresent. But back in the Nineties, Kim was a revelation: a tough, sexually liberated, new-age feminist whose star wattage blazed so brightly that an appearance here by Brooklyn up-and-comer Jay-Z seemed downright pedestrian. —K.M.

By 1994, Gang Starr were one of the most acclaimed hip-hop groups in New York. But the Brooklyn duo, a pairing between the late Boston MC Guru and Texas émigré DJ Premier, was frequently misclassified as “jazz rappers,” a sobriquet that suggested their work wasn’t as tough or street-oriented as their peers. “Mass Appeal,” the lead single from their fourth album,Hard to Earn, destroyed that misconception once and for all. It finds Guru rapping “calm” yet “wild” with his “monotone style,” while Premier turns a jazz-fusion sample into a grimy boom-bap groove that pulses with nocturnal energy. There’s nothing jazzy about it at all, and Premier’s turntable cuts of Big Daddy Kane’s “Raw” and a stray line from Da Youngsta’s “Pass Da Mic (Remix)” sound like a line in the sand separating pop and radio gimmicks from the hardcore elite. —M.R.

“Rock the Bells” was the hardest-rocking, hardest-boasting track from a teenage sensation with unlimited confidence: If LL Cool J wasn’t the greatest rapper of all time in 1985, he certainly acted like it. One of the earliest productions from Rick Rubin, “Rock the Bells” mixed go-go rhythms with sharp guitar stabs — incredibly heavy at the time and a turntablist staple to this day. “This came from hearing old-school rappers and old records in the street, mixtapes. It was a phrase that was creeping around,” Cool J told Entertainment Weekly about the title, which lives on as a SiriusXM radio station and a music festival. —C.W.

When director Spike Lee asked Public Enemy to compose “Fight the Power,” the incendiary anthem for his 1989 landmark drama, Do the Right Thing, New York was a racial powder keg ready to explode. Booming orator Chuck D, irreverent hype man Flavor Flav and revolutionary production crew the Bomb Squad created a sample-stacked rallying cry for Black pride that called out white supremacy, community apathy, and the cult of Elvis Presley (“Motherfuck him and John Wayne!”). “I feel like Pete Seeger singing ‘We Shall Overcome,’ ” Chuck said of the song’s defiant message. “Fight the Power” points to the legacy of the strengths of standing up in music. —K.M.

Puff Daddy didn’t invent the rap remix, but he arguably perfected it with “Flava in Ya Ear,” proving that sometimes lightning can strike twice. “Flava” was already a hit for Craig Mack, but it got a second life thanks to this all-star cipher of New York’s most formidable rappers: Rampage the Last Boy Scout remembers that Biggie, Puff, Cool J, and Busta were all present in the same session. The high-octane Busta verse primed the pump for his solo debut, the knotty LL Cool J verse reasserted his legendary status after the mixed response to 1993’s 14 Shots to the Dome, and the show-stealing Biggie verse helped launch an icon. “Craig Mack is like, ‘This Mickey Mouse beat, man … I don’t know what the fuck I’mma do on this,’” producer Poke told Complex about the now-indelible Easy Mo Bee production heard on both versions. “And so we had this 30-to-50 minute argument. Puff was jumping up and down kicking the walls like, ‘N***a, if you don’t rhyme on this fucking record!’ He was going in.” —C.W.

Originally released on the soundtrack to the Jackie Chan and Chris Tucker vehicle Rush Hour, this party-starting battle of the genders was a landmark recording for all three of its MCs. Jay-Z found the perfect balance between the gritty raps of 1996’s Reasonable Doubt and the glossier pop on his maligned second album, 1997’s In My Lifetime, Volume 1, resulting in 1998’s Vol. 2 garnering his first of many platinum plaques. And it was a career-making moment for the serpentine Amil, the gruff Ja Rule, and producer Irv Gotti — the last two would end up dominating rap radio for the next few years thanks to the soon-to-be-minted Def Jam imprint Murder Inc. The track was originally intended for Ja Rule’s album, but Jay-Z asked if he could take it for his own. —C.W.

Brownsville, Brooklyn’s Mash Out Posse were the hardest of the hardcore at the turn of the millennium. The shoutfest “Ante Up” was their pugilistic peak — an exhilarating, frenetic, hard-rock record that unleashed fans’ inner stickup kid. “People just think it’s a robbery record,” M.O.P.’s Billy Danze told Passion of the Weiss, “but for me, when I actually think about it, the track was more about our careers at the time and the music business as a whole. We had already put out three albums by that point and smashed everybody when it came to live shows onstage.… But still we were not getting our due respect.” The record was elevated to new heights thanks to a remix with Busta Rhymes, Teflon, and a young Remy Ma, who recorded her breakout verse while freshly mourning the passing of her mentor Big Pun and pregnant with her first child. —S.I.

The Nineties’ East Coast vs. West Coast hip-hop beef proved highly exaggerated. A far more authentic conflict took place between backpackers and shiny-suit men: rappers who held originality and lyricism in the highest regard vs. more commercially minded stormers of the mainstream gates. Eventual billionaire Sean “Puff Daddy” Combs, the Shiny Suit Man himself, enlisted producer Deric “D-Dot” Angelettie to craft a walloping beat for his unabashed celebration of materialism with Jadakiss and Sheek Louch of the Lox for mixtapes in late 1996. (D-Dot’s coup de grâce? A decelerated guitar lick from Love Unlimited’s “I Did It for Love.”) Puff added one of Lil’ Kim’s most signature stanzas months later, along with his Bad Boy record label’s newly deceased marquee artist, Biggie Smalls. —M.M.L.

Before any of her 100-plus Billboard Hot 100 appearances, Nicki Minaj was a mixtape sensation, an up-and-comer spitting highly technical, idiosyncratic rhymes on her 2009 breakout, Beam Me Up Scotty. The relentless “Itty Bitty Piggy,” featured Minaj at her rawest, making cheeky rhymes and unpredictable melodic detours over the beat from Soulja Boy’s “Donk.” The brash attitude and limitless swagger that spawned an army of Barbz was there from the beginning: “I’m gettin’ the munchies/I think I’ll have a rap bitch for my entrée/’Cause they be thinking they can spit, spit shine my shoes.” —A.L.L.

The late drill innovator Pop Smoke possessed a disarmingly gruff voice that echoed the rough underbelly of the Canarsie, Brooklyn, streets that raised him. And yet the hypnotic “Dior” displayed an artist who also could deliver alluring yet intricate club bangers. Even when Pop flexes (“When I walk in the spot, 30 on me …”) he’s still an engaging character. Sadly, the charismatic spitter was gunned down in Los Angeles in early 2020, before he had time to witness the lane he helped create for future NYC drill stars like Fivio Foreign, Kay Flock, and Ice Spice. —K.M.

As hip-hop posse cuts go, you would be hard pressed to find a more exhilarating rap-along than A Tribe Called Quest’s “Scenario.” Its power lies in its unbridled relentlessness, from the late Phife Dawg’s off-the-rails punch lines (“Bust a nut inside ya eye to show you where I come from …”) and the crowd-amping theatrics of Leaders of the New School’s Charlie Brown and Dinco D, to singular Tribe frontman Q-Tip passing the mic to a 19-year-old Busta Rhymes, who unleashed an unforgettable A Star Is Born moment. —K.M.

The party-crashing minimalist noise that killed disco-rap dead. Run-D.M.C. ushered in hip-hop’s new school with this booming, boasting B side that instantly replaced the slick studio bands of labels like Sugar Hill Records with the steady artillery of the Oberheim DMX drum machine. The lyrics were simply one of Run-D.M.C.’s practiced routines with a few tweaks, its bare-bones sound aspiring to capture the energy of a block party, not mainstream records. “To radio programmers, ‘Sucker MC’s’ was the absolute worst record on the radio in years,” Joseph “Run” Simmons wrote in his memoir. “No one could even imagine what the fuck it was. No melody. No harmony. No keyboards. Just a beat, some fake-sounding handclaps and these n****s from Queens yelling over the track. For that record to be a hit on the radio baffled all the people whose job it was to know what good music is.” —C.W.

A timely response to the excessive, luxury-driven aesthetic of the Bad Boy era, “Get at Me Dog” was a thugged-out wake-up call, reminding listeners that the streets are the essence of hip-hop. Irv Gotti, one of the song’s executive producers, once explained to a blossoming Jay-Z that DMX would win because more people related to struggle than prosperity. And DMX brought this point full circle with the couplet, “I’m just robbing to eat, and there’s at least a thousand others like me mobbing the streets.” Reenacting a pitbull’s gruff bark (on top of a memorably aggressive hook), X established a stark sense of authenticity — assuredly cementing “Get at Me Dog” as one of the pivotal songs of the late 1990s. —J.F.

In the summer of 2017, Cardi B laid the framework for her total domination, shifting from a reality-TV rap hopeful to a bona fide hitmaker with “Bodak Yellow.” It crept into the American consciousness just like its beat crawls from gentle menace to full-forced terror, with a rap from Cardi as vicious as it is earnest. It took balls and charm to turn a bar about her formerly imperfect teeth into a source of superiority — and to borrow the flow of a distinctly different rapper and make it completely her own (with credit). She said that when she first heard the track, courtesy of her producer J. White, “Every bitch that I don’t like came to my head … and I pictured me, slapping it to them.” Cardi’s nose is in the air and her foot is on your neck all over the track, and bad bitches everywhere still rejoice in the mayhem. —M.C.

Dancer Troy Dixon of Heavy D and the Boyz, professionally known as “Trouble” T. Roy, accidentally fell from a two-story height while on tour in 1990 and died at age 22. His elegy — penned by C.L. Smooth and produced by Heavy’s cousin, the legendary Pete Rock — became one of the most universally recognized and beloved songs in hip-hop history. Centered on sax and bass from Tom Scott and the California Dreamers’ cover of the Jefferson Airplane folk-rock ballad “Today,” Smooth’s slice-of-life reminiscences make it the greatest hip-hop tribute ever recorded. In 2007, Rock told The Village Voice, “When I mixed the song down … we all just started crying.” —M.M.L.

Nas opened his seminal debut, Illmatic, with a sneering, revelatory statement. “I’m like Scarface sniffin’ cocaine/Holdin’ an M16, see, with the pen I’m extreme,” the kid from theQueensbridge projects proclaimed on the menacing DJ Premier-composed track “N.Y. State of Mind.” This song, and Illmatic, hailed Nas as the Nineties inheritor to Rakim’s crown. “I’ve been rapping in the 2000s longer than I have been in the ’90s,” Nas said in 2020, “but I still represent the ’90s in everywhere I go, even if the music is different and sounds fresher, newer, I still bring that time with me in the music.” —K.M.

Self-declared kings of rock Run-D.M.C. came for it all on their third album, the Rick Rubin-produced Raising Hell, beginning with this double A-side single. Name-checking nursery rhyme characters for a tribute to their DJ, Jam Master Jay, the Queens MCs made unforgettable use of the cowbell intro from Bob James’s 1975 cover of Paul Simon’s “Take Me to the Mardi Gras” (played by percussionist Ralph McDonald, popularized in Bronx park jams by Grandmaster Flash), under a tag-team delivery recalling the legendary Cold Crush Brothers. LL Cool J had wanted that same breakbeat for “Rock the Bells” (hence the title). After “Peter Piper,” he went back to the drawing board. —M.M.L.

Bobby Shmurda’s rambunctious “Hot N*gga” all but ruled 2014. Initially rejected by Meek Mill before resurfacing later as a Lloyd Banks freebie, the grisly track — consisting of sirens and an eerie church-like organ — went to another dimension once East Flatbush’s GS9 representative threw his hat into the ring. The Catch-22 here is that Shmurda’s energy and roguish charm turned his life around — but the NYPD used his lyrical confessions against him, and detailing the true-to-life misdeeds of his comrades played a role in his serving a seven-year prison stint. Famous for Shmurda’s now-notorious toss of his Knicks cap and bold two-step, the song’s rowdy video hit over 850 million YouTube views and set a precedent for the rise of New York’s ubiquitous drill sound. —J.F.

Lauryn Hill came out swinging at the start of successful solo career, frontloading her landmark debut album, The Miseducation of Lauryn Hill, with a venomous diss track that many assume is aimed at former Fugees bandmate and ex-lover Wyclef Jean. Though the Grammy-winning album seamlessly blended neo-soul, R&B, hip-hop, reggae, and a heroic Carlos Santana guitar solo, “Lost Ones” was pure boom-bap, with Hill effortlessly shooting lyrical daggers: “Your movement’s similar to a serpent,” she raps. “Tried to play straight, how your whole style bent?” Fellow Fugee Pras confirmed that Jean thought the song was about him, but when asked directly by VladTV,Jean said, “I wouldn’t know that. I think that y’all would have to interview Lauryn Hill. Personally, I don’t take it as a shot at me.” —A.L.L.

Rap fans of a certain age will never forget the moment they saw the “Shook Ones” video, where the late Prodigy strode confidently toward the camera, Solo red cup full of liquor in his hand. He looked terrifyingly real as he delivered one of the most famous verses in hip-hop history: “I’ve got you stuck on the realness/We be the infamous/You’ve heard of us/Official Queensbridge murderers.” Actually, Prodigy was originally from Hempstead, Long Island; he met Queens rapper Havoc when both attended the High School of Art and Design in Manhattan. Signed to 4th& Broadway in their teens, the two issued a 1993 debut,Juvenile Hell, that got middling reviews. Back in the lab, Havoc devised a coldly minimalist sound inspired by jazz downbeats and their crew of friends in Queensbridge. The result is a cornerstone of what became known as thug rap. “All we cared about was makin’ some gangsta shit thatweliked,” Prodigy told Brian Coleman inCheck the Technique: Liner Notes for Hip-Hop Junkies. “If we was gonna like it, then the world was gonna like it.” —M.R.

Amityville, New York-based trio De La Soul’s debut single, “Plug Tunin’,” sounded like little else before it. The sound of hip-hop in 1988 was funky like James Brown, with maybe a little hip-house or New Jack Swing thrown in. By contrast, “Plug Tunin’” had a loping pace akin to a soul 45 played at 78 RPM and seemed enveloped in crackly hiss. Before he passed away in February 2023, Dave “Trugoy the Dove” Jolicouer told Rolling Stone that with “Plug Tunin’,” “we also knew we had something totally obscure, something totally different.” It begins with DJ Maseo announcing, “Yo, Pos and Dove, stand clear to be clear to be plugged up into line one and two so y’all can flaunt that new style of speak.” Trugoy and Posdnous then rhyme utilizing cryptically organized phrases and in-jokes over a patchwork of obscure samples knitted together by the group and mentor Prince Paul, and they punctuate each verse with a dusty voice crooning, “mmmm-yeah.” The song was subtitled “Are You Ready for This?” — and truth be told, not everyone got it on first listen. But even “Plug Tunin’” skeptics eventually realized De La Soul were on the verge of creating something special. —M.R.

Jay-Z was arguably King of New York in 1999 when he dropped this DJ Premier-produced deep cut. Kicking some of his cleverest bars ever, Hov proved why he belongs on rap’s Mount Rushmore.“So I’m cruisin’ in the car with this bougee broad/She said, ‘Jiggaman, you rich; take the do-rag off’” perfectly summarized his role as around-the-way Forbes fave. Jay was already richer than God when he dropped Hard Knock Life Vol 3 … Life and Times of S. Carter. But where most rappers would have mainlined the models-on-an-exotic-vacay thing (à la the “Big Pimpin’” video), he cranked out this caustic banger. No yachts here — just guns at the Grammys, bottles on the White House lawn, and endless, effortless swag. —W.D.

Before the release of Eric B. and Rakim’s pivotal introductory single, rappers could inhibit the role of chief party rocker, wise street poet or around-the-way B-boy. That all changed with “Eric B. Is President.” Not only does it boast arguably the genre’s most iconic first line (“I came in the door, I said it before …”), the influential jam single-handedly expanded the syntax of rap. Over Marley Marl’s uncredited flip of Fonda Rae’s 1982 post disco gem “Over Like a Fat Rat,” Rakim displays a commitment to his craft that set a new standard; he’s not even the protagonist of his raps, his beguiling mic is, “fighting” and “inviting” the most revered writer of hip-hop’s golden age to rhyme. Hip-hop lyricism would never be the same. —K.M.

“It was the first dominant rap group with the most dominant MC saying something that meant something,” Public Enemy’s Chuck D once said of “The Message.” Indeed, few songs have rerouted the artistic and cultural possibilities of a genre like this synth-funk shot of stark, confrontational, inner-city realism. Written in 1980 by rapper and musician Duke Bootee,a member of the Sugar Hill Records house band, and originally titled “The Jungle,” the song caught the ear of Sugar Hill label owner Sylvia Robinson, who asked the Furious Five’s Melle Mel to add some verses. The results moved hip-hop’s focus beyond post-disco party jams and out into the mean streets of a New York reeling from years of neglect and apathy. Over four decades later, it remains the template for political rap records. —J.D.

“Juicy,” the Notorious B.I.G.’s quintessential rags-to-riches debut, is so enthralling that rap purists could not deny the sheer perfection of this radio-or-bust single. Just a year earlier, he was seemingly content with rocking New York’s grimy underground with the spirited Who’s the Man soundtrack throw down “Party and Bullshit.” But Biggie’s 1994 anthem “Juicy,” the anchor to his six-times platinum Ready to Die, would spark the East Coast’s return to commercial glory following a few years of West Coast dominance. Here B.I.G.’s gifted storytelling is on full display: fantasies of limo rides with Salt-N-Pepa and Heavy D; memories of being so broke that “birthdays was the worst days”; images of going from getting chased by the cops to achieving Champagne-soaked stardom. It’s still jarring hearing Christopher Wallace detail his perilous, violent crack-dealing days over a sample of Mtume’s early Eighties bowtie R&B. But Biggie goes beyond mere myth-making here. He encompasses the American Dream. —K.M.

The sample on P.E.’s iconic 1987 single hits like a canister of mustard gas landing next to a sax player riffing on John Coltrane. But everything about “Rebel Without a Pause ”— that searing sax glissando and those cranium-piercing snares — still sounds anthemic. Save for Grandmaster Flash and the Furious Five’s “The Message,” rap music with a conscious outlook was nonexistent until “Rebel Without a Pause.” Chuck D’s bold flow and Flava Flav’s blithe ad-libs cracked the whole culture open.Chuck honors Assata Shakur after dismissing mainstream radio. But the Bomb Squad’s joyously abrasive soundscapes — evoking a soiree in a fallout shelter — are made to charm multitudes. —W.D.

In this song, built from the piano trill of the Charmels’ “As Long As I’ve Got You,” Wu-Tang MVPs Raekwon and Inspectah Deck reminisce on hardscrabble childhoods as Method Man spits the instantly infectious hook spelling out the title’s acronym: “Cash rules everything around me, cream get the money, dollar dollar bill, y’all.” RZA first laid the foundation for “C.R.E.A.M.” in his Stapleton Houses apartment studio in Staten Island as an early demo. And its reverberations shockwaved throughout an early Nineties hip-hop culture then dominated by the G-funk sound of Dr. Dre and Snoop Dogg. Prior to the debut albums of Nas and the Notorious B.I.G. in 1994, Wu-Tang reclaimed “the crime side, The New York Times side” of NYC as a center of focal attention.“Meth came up with the hook, but our dude named Raider Ruckus — this was like Meth’s homeboy back then, like they was real close — he came up with the phrase ‘cash rules everything around me’, ” Raekwon told Complex in 2011. The Wu-Tang wordsmiths’ minute details — fire escapes, ball courts, incarceration, smoking weed in staircases, depression — make this rap classic a microcosm of inner-city blues for the ages. —M.M.L.