The 200 Greatest Hip-Hop Albums of All Time

Everywhere you went in the summer of 1988, you heard EPMD — two suburban dudes from Strong Island with their own hypnotic funk sound, perfect for backyard barbecues. “Strictly Business” was their theme song: Erick Sermon and Parrish Smith talking their shit, looping “I Shot the Sheriff” into a whole new futuristic groove, with woofer-eating bass designed to blow up Jeeps. As Sermon said, “It was just two kids who heard wack stuff on the radio and wanted to do better.” Their debut is a true summer classic, pioneering the laid-back but menacing sound that would take off on the West Coast as G-funk. —R.S.

When N.W.A recorded Straight Outta Compton, they weren’t calling their music “gangsta rap,” it was “reality rap.” Tracks like “Gangsta Gangsta,” “If It Ain’t Ruff,” and “Straight Outta Compton” reflected the everyday lives of proud former gangster Eazy-E, producer-DJs Dr. Dre and Yella, and lyricists/news anchors Ice Cube and MC Ren. Some tracks were misogynistic (“I Ain’t tha 1”), some were about drinking and driving (“8 Ball”), some were about dealing drugs (“Dopeman”), and all we’re about not giving a fuck. The record’s most incendiary track, “Fuck tha Police,” was “400 years in the making,” according to Ice Cube. —K.G.

The Detroit beatmaster made most of Donuts in his hospital room, as he lay dying from a rare blood disease. Dilla knew he didn’t have time to waste — he died three days after the album dropped. But he packs a lifetime’s worth of sonic imagination into these instrumental grooves. Donuts is wildly inventive mixology, 31 brief fractals that weave in and out of each other, a swirl of funk, soul, cartoon music, and prog rock. Jay Dee came out of the 1990s Soulquarians scene, but here he’s alone with the music — throwing all his brilliance into one last gift to the world. —R.S.

Two weeks: That’s how long it took for Missy Elliott and Timbaland to build an album as seminal and mind-bendingly avant-garde as Supa Dupa Fly — testament to the alchemical connection between the two sonic architects. Hours in a studio in Virginia, where they both grew up, produced one otherworldly experiment after another, shaping songs that featured era-defining stars such as Aaliyah, Lil Kim, Busta Rhymes, and more, and that sounded like transmissions from a distant, futuristic planet. Standouts such as “The Rain,” boosted by a choir of crickets, and the soul-powered “Sock It 2 Me” spun the music world in a new direction and made Missy one of music’s most groundbreaking polymaths. —J.L.

On Call Me If You Get Lost, Tyler, the Creator entered his 30s with the most ebullient version of his confounding, agitating, engrossing music yet. With mixtape icon DJ Drama on board, the album struck a fragile peace with the hip-hop tradition Tyler had upended when he first disrupted the scene with Odd Future in the late-’00s, and something almost like generosity governed much of the record. Even its menacing tracks were dazzling, and the moments of R&B-inflected prettiness (especially the lush, genuinely crushed-out “Wusyaname”) were downright heartwarming. When Tyler opened up (looking back on his shock-rap early days on “Manifesto,” rapping about his mom’s hardships on “Massa”), he imbued his kaleidoscopically irascible sound with a a bracing personal gravity. —J.D.

At this point in LL Cool J’s career, he released an album with one goal — to reign over hip-hop as its undisputed MC champ. After obliterating all comers on 1987’s exhilarating taunt Bigger and Deffer, he lost his title on its scattershot follow-up. Here, he got in the ring, literally, throwing haymaker punchlines in the video for the Grammy-winning title track. Crucially, production maestro Marley Marl returned, and his kinetic bang-zoom stoked LL’s joy at bending language to his will and flicking syllables like precise, stinging jabs. —C.A.

The most Wu-ish of the Wu-Tang solo projects is also one of the best. Released during RZA’s pre-flood apogee, Liquid Swords is a masterful melange of five-percenter-inspired lyricism, Zen koans, and life-is-a-chess-game philosophy. GZA’s debut delves straight into those 36 chambers, from which he blesses us with myriad methodical darts emboldened by his quiet charisma. “My preliminary attack keep cemeteries packed/Of niggas who think it ain’t like that,” he asserts on “Living in the World Today,” as if he’s gifting you a fatalist fortune cookie. The God-body-invoking title track could make even an imbecile know today’s mathematics. —W.D.

There is before Run-D.M.C. and after Run-D.M.C., and the after still reverberates almost four decades later. The group’s debut, hip-hop’s first gold-selling album, reduced the genre to its elemental boom — MCs Joey “Run” Simmons and Darryl “D.M.C.” McDaniels were alternating bullhorns; producer Larry Smith codified noise as rhythm via DMX drum machine, stabbing synths, and Jam Master Jay’s brash turntables. Turning Melle Mel’s poetic social commentary into a blunt worldwide edict, they also reinvented and dethroned rock & roll. —C.A.

“Pardon my expression, but I’m-a tear shit up,” Kane says in “Raw,” and he spends his classic debut doing that. Bed-Stuy’s Antonio Hardy was the deadliest wordsmith of the Golden Age, every MC’s favorite MC. He made his name with the Juice Crew in Queensbridge, alongside his high-school homie and lifelong friend Biz Markie. (Kane ghostwrote the Biz’s first hits.) He claims his crown on Long Live the Kane, with producer Marley Marl, crushing the competition with his lethal warp-speed wordplay. As he warns in “Ain’t No Half-Steppin,” “Rappers, you better be ready/To die because you’re petty/You’re just a butter knife, I’m a machete.” Slay on, Big Daddy. —R.S.

There’s an entire population, currently in their 20s, who remember seeing the music video for “Gold Digger” for the first time when they were kids. The lead single from Kanye West’s sophomore album, 2005’s Late Registration, brought the poignant, sample-flipping virtuoso to the masses and set the stage for one of rap’s most undeniably brilliant runs. On Late Registration, Kanye’s hubris hadn’t yet calcified in his image. He was hungry because of how great he knew he was, and he was hell-bent on proving it. The result is a once-in-a-generation record that today’s millennials will be sharing with their grandchildren. —J.I.

The first album released by Death Row/Interscope was landscape-changing. Its swelling, synthesized bass lines, Parliament samples, and raucous anthems became the trunk-rattling standard for West Coast gangsta rap. Matching trampoline beats with charismatic writers, most importantly a then-unknown Snoop Doggy Dogg, The Chronic was brisk, concise, and immediately memorable. Thirty years later, any song on the record — “Wit Dre Day” or “Nuthin’ But a ‘G’ Thang” or “Deeez Nuuuts” — can still get heads nodding with hypnotized affection because, among other things, The Chronic remains one of the best party records of all time. —Y.P.

The third album in Lil Wayne’s auteristic Carter series was not the no-holds-barred rhymefest heard on the deluge of mixtapes spilling from the guy everyone was calling “the greatest rapper alive”: It was something else entirely. Sure, “A Milli” and “3 Peat” were dizzying showcases of peak Wayne, but the album also brought Weezy the pop alien, Weezy the sex symbol, and Weezy the industry game-changer: The prescient, woozy “Lollipop” would almost single-handedly drag hip-hop into the Auto-Tune era. He still loved off-kilter metaphors (“I ain’t kinda hot, I’m sauna/ I sweat money and the bank is my shower/Ha ha, and that pistol is my towel”) and insane rhyme gymnastics, but Tha Carter III showed he still loved hooks. —C.W.

Kendrick Lamar channeled eons of trauma and knocked it out the park on his classic debut, which is Bompton’s equivalent to Black Boy. Like a millennial Richard Wright, the future Pulitzer winner poeticizes pain on the claustrophobic title track, describing a murder he witnessed in his youth in a fake-nervous whine that makes the hairs stand up on your neck. “The Art of Peer Pressure” is a riveting Bildungsroman, in which being young, Black, and impoverished means making bad decisions. One of these kids is doing his own thing; he just happens to be this generation’s greatest rapper. —W.D.

The Wu-Tang empire reached glorious heights in 1995, spinning off classic solo joints from Ol’ Dirty Bastard and Genius/GZA. But Raekwon’s mob epic towered over them all. On Cuban Linx, Raekwon paired up with his Wu sidekick Ghostface Killah for the ultimate double-threat rap dream team. It’s the story of two young hustlers trying to grab one last score, before it’s too late. The RZA brings his trippiest production to their Shaolin street tales, mixing true mathematics with gangster flicks. As Masta Killa said, “RZA was the Beethoven of the whole shit.” Rae and Ghost take their “Wu-Gambinos” concept to a Goodfellas peak, in hard-boiled narratives like “Incarcerated Scarfaces.” —R.S.

The crown jewel of the blog era, Acid Rap made Chance the Rapper worthy of the inescapable hype that followed its release. No one was rapping like Chance — no one was equal parts poetic and playful like him, no one was as brash and as melodic. Like his idol Kanye’s College Dropout, his breakout mixtape traverses very silly thoughts, very hopeful themes, and very real fears with an intense and, at the time, unparalleled musicality. You can feel Chance’s commitment to his community, his family, his joy, and most importantly, his art, throughout. —M.C.

To brag, I was drinking gin and juice in the studio with Dr. Dre and Snoop during the Doggystyle sessions, so I watched (briefly) as Dre integrated a revolving door of rappers, singers, live musicians, et al. into an audaciously swinging, digitally contoured, crushed-velour tapestry of Blaxploitation funk. With Snoop’s slithery, sly flow, the album eventually went 11-times platinum worldwide. While The Chronic‘s X-rated gunclaps wafted through the haze of the L.A. Uprising, Doggystyle was the scandalous, bong-ripped afterparty. —C.A.

Founded by R&B veterans Sylvia and Joe Robinson in 1979, Sugar Hill Records defined the early rap landscape. It scored the first Top 40 rap hit in Sugar Hill Gang’s “Rapper’s Delight”; the first important rap act in Grandmaster Flash & the Furious Five, who released the turntablist gem “Grandmaster Flash on the Wheels of Steel” and the socially conscious classic “The Message”; the first major female rap group (and first Southern hip-hop act) in the Sequence; and even the first group to appear on national TV, thanks to the Funky Four + 1 More’s 1981 appearance on Saturday Night Live. Sugar Hill’s seminal catalog largely consists of standout 12-inch singles, which makes this compilation of its peaks so crucial. —M.R.

De La Soul’s debut album is a landmark of the genre, a feat of imagination and creativity impossible to duplicate. That’s not only because the samples used — from Steely Dan’s “Peg” to Daryl Hall and John Oates’ “I Can’t Go for That (No Can Do)” — would be prohibitively expensive now. The trio along with mentor-producer Prince Paul craft a private language defined by jokey juvenilia (Luden’s cough drops and the 1970s exploitation film Bloodsucking Freaks) and dense allegories like “Potholes in My Lawn,” a metaphor for MCs trying to copy their unusual style. The latter sentiment proved hopeless: De La Soul made a beacon for quirky, left-of-center hip-hop that yielded innumerable followers, all entranced by the power of the D.A.I.S.Y. Age. —M.R.

There is still nothing that feels like “Love Sosa,” the breakout single from a then 17-year-old Chief Keef, from his debut album, Finally Rich. The Chicago rapper’s melodic, hard-nosed anthem shook the foundation of hip-hop. The kids were taking control in a way that the genre had never seen. And why not? Keef’s sound was at the heart of Chicago’s enduring drill movement, populated by young MCs whose lives are tinged with as much violence as the prior generation’s old heads. There’s a menacing atmosphere throughout Finally Rich, but not enough to eclipse the feeling of triumph. Keef’s ethos booms loudly and full of feeling. Proof that the kids are alright. —J.I.

After slaughtering on a series of mixtapes and high-profile cameos such as Kanye West ’s “Monster,” Nicki Minaj made her debut LP a regal announcement of her new status as hip-hop queen: “Got two shows tonight, Brooklyn and Dallas/Then the private party at the Buckingham Palace.” The guest list ranged from Rihanna to Kanye to Drake, but no one got in the way of Nicki herself, showing off her razor-sharp R&B crossover instincts (the vulnerable “Save Me”), brash rhymes, and hydra-headed flows. The result proved you could own the charts without dialing back your confrontational individuality, and it set the table for a generation of artists from Cardi B to Megan Thee Stallion to Doja Cat. —J.D.

Weirded out by the frat-boy fanbase they’d accrued after their debut, License to Ill, became a runaway success, the Beasties decamped to L.A., hooked up with sampledelic production crew the Dust Brothers, and created one of pop music’s all-time great left turns. Sampling everything from the Beatles to Dylan to the Funky 4 + 1, rapping about drive-by eggings, The Flintstones, and the schism of racism, they went from playing beer-brained dicks to becoming true boho pied pipers, leading a whole generation toward a cooler, doper, more open-minded tomorrow. —J.D.

Everything bedeviling Tupac Shakur — mortality, black humanity, rivals real and imagined, media notoriety, Suge Knight — ripples, shudders, and blusters inside of All Eyez on Me‘s 27 precisely defiant songs. The just-free-from-prison MC auteur enlists a cast of superb, fully invested voices (Snoop, Nate Dogg, Method Man, E-40, et al.) and studio hands (Daz, Johnny J, DJ Quik, Dr. Dre) to match his gusher of exacting energy. It’s all personal, political, life, death. And “California Love” makes it rain blood money. It’s a goddamned masterpiece. —C.A.

If Mobb Deep’s second album had just been “Shook Ones, Pt. II” 10 times in a row, it would still be a first-ballot hall-of-famer. The late, great Prodigy’s opening verse alone is full of shiver-inducing bars that belong in a Norton Anthology of Poetry, from “Rock you in your face, stab your brain with your nose bone” to “I’m only 19, but my mind is old,” and Havoc’s droning, plinking beat is minimalist gold. But “Shook Ones” is only one of many unforgettable moments on the ruggedest jewel of New York rap’s crowning era. On tracks like “Survival of the Fittest,” “Eye for an Eye,” “Trife Life,” and “The Start of Your Ending,” P and Havoc create a unique world of menace and mystery, turning cold-hearted threats into the height of cool. —S.V.L.

“It’s him and I/Aquemeni,” raps André 3000 on the album’s title track, establishing him and Big Boi as one of hip-hop’s all-time great duos, two halves of the same jiggy coin. Aquameni proved the South in general and Atlanta in particular were hip-hop and American pop’s next frontier.  Funky, filmic, and forward-looking, the album liberated their artistic impulses by shifting their evocative storytelling to left-of-center compositions like the driving “Rosa Parks” and “Skew It on the Bar-B” where Raekwon spits allegiance with his fellow avant-rappers. There was no way to know they would hit greater heights with Stankonia, but Aquameni still sounds like the future. Inspirational verse: “I said what you wanna be, she said, ‘Alive’.” —J.G.

There was a cultivated inevitability around Reasonable Doubt — Jay-Z’s rep as a freestyle MC with a hot demo, kingpin image, and discreetly funded label that he co-founded (Roc-A-Fella), industry connects (Big Daddy Kane cosign, A-list beats, Biggie, Mary J. Blige features), plus a single (“Ain’t No Nigga,” featuring Foxy Brown) already rockin’ New York clubs and radio. But this crisply refined record elevated Jay to an elite artistic, if not yet commercial, level. He had the ruthlessly lucid crime lore, subtle shifts in dialogue and point of view, you-conceited-bastard wordplay, and haughty C-suite vision. The result: Hooky, poignant champagne-soul, from a sage with well-earned scars. —C.A.

Post The Slim Shady LP, national Eminem kibitzing began to boil. Reading the room, the devilish, blue-eyed MC cranked the heat and the combustible debate ignited: Was he a hateful scourge or an artistic prankster? That debate became his most fruitful inspiration. Here, he crafts a series of riveting one-act plays: a fan writes him disturbing letters; he threatens matricidal revenge; he has a psychotic break and screams at his wife. Buoyed by Dr. Dre’s vivid production, he even enthralled Nobel Prize-winning poet Seamus Heaney. —C.A. 

The first on-record appearances of “Nasty” Nas (Main Source’s “Live at the Barbeque,” “Halftime” from the Zebrahead soundtrack) were like Shakesperean, fuck-thou freestyles resituated into songs in the studio. But Illmatic‘s tight, 10-track set cast a timeless spell — project poetry with documentary depth and vocalese so subtly resonant you could see and smell the Queensbridge Houses stairwells. Ultimately, Nas’ musings were the intuitive philosophy of a 20-year-old old soul, but the roll call of masterful producers — key man Large Professor, plus Pete Rock, DJ Premier, and Q-Tip — artfully shaped the songs with such affecting jazz-funk brush strokes that they felt divinely inspired. —C.A.

Ridin’ Dirty marks UGK’s creative peak. Everything is deeper here: The bluesy rhythms are richer and slower – yep, that’s guitarist Leo Nocentelli from the Meters on “Diamonds & Wood” – and the performances are razor sharp. The late Pimp C established himself as one of the genre’s greats, a dynamic Southern producer who could rap and sing with equal finesse. Meanwhile, Bun B stands out for his aggressively textured lyrics, and he blacks out on “Murder.” The album vividly evokes the sensation of smoking out and drifting through the Texas streets, a time and place of that resonates decades later. —M.R.

Emerging from a childhood scarred by poverty, abuse, and incarceration, Earl “Dark Man X” Simmons came hungry and heartfelt on his five-times-platinum debut. In 1998, he was the undisputed hottest rapper in the game because of his technical ability on songs like single “Get at Me Dog,” but his debut LP revealed a multifaceted, emotionally rich tangle of contradictions and confessions. X was boastful (“Ruff Ryders’ Anthem”) and prone to grisly murder scenarios (“X-Is Coming”), but he takes a moment for an earnest, a cappella prayer to the heavens (“Prayer”). He raps as temptation (“Damien”) and as God (“The Convo”), airing his demons and aspirations, painting both the horror of his existence and the power of his triumph. —C.W.

Has any artist hit a hot streak like Lil Wayne circa 2007? The New Orleans MC was on fire, stunting with a barrage of brilliant underground mixtapes that made everyone else in the game look slow. Da Drought 3 was his crazed peak, two discs of Weezy cruising to Anita Baker and smoking weed by the acre, in his blunted-out Louisiana drawl. (It also had the first showcase for his new discovery, Nicki Minaj.) The high point: “Upgrade,” where Weezy freestyles over a Beyoncé hit, declaring, “Put a motherfucker on ice like the Maple Leafs/That’s a hockey team, and I ain’t on no hockey team/But I’m a champion — where’s the fucking Rocky theme?” —R.S.

From the hedonistic chaos of “Freak Hoe” to the diamond-encrusted self-promotion of “Rich Sex,” Future’s double-platinum opus is the dark lothario at his best. For years after its release, there was not a college party or apartment pregame that went un-soundtracked by DS2, and ever since, wherever there are vices to be enjoyed among rap fans, there is some Future record to be played. Plus, by tacking on modern classics like “Fuck Up Some Commas” and “Real Sisters,” DS2 presents a rare instance in which a deluxe repackaging actually enhances the original album rather than bloating it. —M.C.

“Inside every man is a bad girl!,” Lil Kim declared in her debut hit, “No Time.” And all over Hard Core, she proved she was that girl. The Queen Bee was the femme in the Bad Boy crew, the self-proclaimed “rap Mae West.” Nobody could top Kim for raunchy sex-and-money talk. She flosses with her mentor Biggie on four of Hard Core’s songs. (Biggie called her “my lieutenant.”) Ironically, her two most iconic hits from this era were remixes she left off the album: “Crush on You” and “Not Tonight,” a Top 10 feminist jam with Missy Elliott, Left Eye, and Da Brat. —R.S.

The one and only Madvillain album has two eccentric hip-hop geniuses pushing each other to a peak of weirdo virtuosity: rapper MF Doom and producer Madlib. Doom started in the underrated Long Island crew KMD, but he became a cult figure on his own, a mysterious supervillain in a metal mask, using a string of aliases and costumes. He had perfect chemistry with Madlib, a West Coast maestro of warped funk samples. As Doom said, the album sessions were “like a telepathy thing. There wasn’t a lot of talking.” Madvillainy was strictly for the underground, but it was so dazzling, so original, nobody could resist. It stands as one of hip-hop’s boldest creative landmarks. —R.S.

With its thick timbres, faster tempos, dissonant keyboards, dynamite drums, and violent mix of hip-hop and electronic music, Kanye’s sixth studio album remains Kanye West’s most radical statement. Nothing in mainstream rap had the hammering percussion of “Black Skinhead,” the glitchy design of “On Sight,” or the ballistic New Orleans bounce of “Blood on the Leaves.” By turning up the distortion, contorting the samples, and rhyming with a petulant recklessness that was over the top even by Kanye’s standards, he found a new way to shock the world. Croissant: earned. —Y.P.

Cardi B built a reputation as Love & Hip Hop’s most beloved “regular degular smegular girl from the Bronx,” but when it came time to release her debut album, Invasion of Privacy, she threw herself into the music with the menace of a Louboutin rammed into someone’s throat. While it was the bellicose spirit of the Grammy-nominated lead single “Bodak Yellow” that set Cardi on course for a history-making career, the greatest achievement of the LP is how it coalesces into a full, unflinching portrait, with songs like “Best Life” and the mega-smash “I Like It” filling in the details of her rise from strip clubs to reality-show fame to hip-hop royalty. —J.L.

Rakim, for all his lyrical complexity, never confused us. (If anything, maybe he was slightly confused — when on his game-changing debut, Paid in Full, he rapped, “My unusual style/Will confuse you a while”—about how palatable his doctorate-in-physics-level rhymes sounded to the average hip-hop head back in 1987.) The timeless title track brought regal God-body purity to lyrics that were otherwise about getting to the bag. And on “Eric B Is President,” Ra dropped science that felt fun and easy as a P.E. course. Neither medicine nor candy, Paid in Full hit a therapeutic sweet spot in the culture. —W.D.

When people mention Ghostface as an all-time great, this is the one they’re talking about. His second solo full-length is Ghost at his purest quintessence, talking miraculous shit for an hour straight and stringing together outlandish imagery at a clip that would leave lesser MCs panting for breath. Lyrical displays like “One,” “Nutmeg,” and “Apollo Kids” — the one where he rhymes “Ayo, this rap is like ziti” with “strawberry kiwi” — fulfill the dreams of anyone who heard his scene-stealing verses on earlier Wu-Tang releases and wondered if he could sustain that energy for an entire album. He could, and it’s telling that an LP that includes Ghost’s first solo chart hit (“Cherchez LaGhost”) is better remembered for the outrageously inventive album tracks that surround it. —S.V.L.

“Guess who’s back,” announces Dr. Dre on the intro to “Still D.R.E.,” as Scott Storch’s cascading piano lines glide beneath him. The multi-platinum success of 2001 barely concealed all the problems Dre overcame to make it. His prior two projects, the 1996 label compilation The Aftermath and the 1997 supergroup The Firm, were commercial disappointments. He lost his brother to gun violence. He even had to change the name from The Chronic 2000 because his onetime business partner-turned-blood enemy, Suge Knight, stole it. These tabloid dramas lend fuel to hard-hitting tracks like “What’s the Difference,” “Forgot About Dre,” and “The Message.” Yet it all sounds like an unforgettable G-funk extravaganza, a hallmark of Dre’s ability to turn tumult to triumph. —M.R.

Real-life brothers Malice and Pusha T had been working with the Neptunes production duo since 1992, making songs in Chad Hugo’s basement despite his screaming parents. Ten years and one shelved album later, they emerged with Lord Willin’, a visionary combination of Clipse’s hard-nosed rhymes about the drug trade and the Neptunes’ futuristic bubble-funk. Single “Grindin’” was the most minimalist thing to hit the radio since “We Will Rock You,” and the rest of the album exploded prismatically with the type of rhymes that blended raw chops, punchlines, and ice-cold veins: Raps Pusha T in “Comedy Central, “I keep the streets so numb they call me ‘Novocaine’/I turn over ‘caine, over and over again.” —C.W.

A whole world of mythology exists in the 80-minutes of Drake’s 2011 opus, Take Care. Kendrick Lamar even finds himself awestruck during his feature on the album’s interlude, “Buried Alive,” essentially realizing that the record is a classic in real time. Indeed, Take Care is the most well-rounded project of Drake’s career, and marks the beginning of a new era in rap. Inspired production from Drake’s right-hand man, Noah “40” Shebib, engendered a dynamic shift in the sonics of hip-hop. Toronto-born Drizzy had already turned the genre’s masculine facade on its head by freely crooning alongside his verses, and with Take Care, the pair achieved sonic cohesion. Drake spends Take Care digging into his psyche, and it set the stage for the vulnerable and self-reflective ethos we see in rap today. —J.I.

Looking to express herself outside the hugely successful Fugees, 23-year-old Lauryn Hill came through with a feminist hip-hop-soul masterpiece on her 1998 debut. The opening one-two punch still stuns: The anthemic “Lost Ones” moves into the brutal breakup ballad “Ex-Factor.” The smash hit, “Doo Wop (That Thing)” is sandwiched between “To Zion,” an ode to her first child, and “Superstar,” a demand for more inspirational mass culture. At 77 minutes long, Miseducation spills over with brilliant (at times contradictory) insights, thrilling melodies, and plenty of moralizing — a righteous blockbuster that redefined every genre it touched. —J.G. 

The epithet “jazz rap” can’t come close to describing what Q-Tip, Phife, and Ali Shaheed Muhammad achieved on their second, classic LP. Though it samples session legends like Grant Green and Art Blakey, Tribe’s masterpiece is a whole multiculti mind state. Cool, eclectic, boho, and Black AF, it covered everything from anger management predicaments to the perils of date rape, and even gave us a random-ass number — 4080 — to sum up all that’s shady about the record industry. Tip’s husky, helium-toned couplets were a perfect match for Phife’s raspy everyman bravado. We still haven’t come down from The Low End Theory’s highs. —W.D.

A hip-hop legend so fantastical, it could only be the truth: Nine guys from New York’s outermost boroughs, steeped in Five Percent teachings and old kung-fu movies, crammed into one smoky studio for a lyrical battle royale that would reshape rap for the next decade. RZA’s sample collages set a new standard for hard-elbowed beats, and the Clan’s verses showed a stunning range of craftsmanship: the multisyllabic wisdom of U-God, the brainy arrogance of Inspectah Deck, the street-level insights of Raekwon, the crooked pop instincts of Method Man, the free-form wit of Ol’ Dirty Bastard, the keyed-up yelp of Ghostface Killah. The sheer density of slang-encrusted myth-making on Enter the Wu-Tang made an entire generation of MCs step up their lingo and laid the blueprint for outsized crews to come from Odd Future to Spillage Village and beyond. —S.V.L.

Missy Elliott’s third album isn’t necessarily an advertisement for MDMA, although she chants, “This is for my ecstasy people” on “4 My People.” But it may be the most evocative reflection of an orgiastic moment when the hip-hop and R&B crowd discovered the delights of the club drug. The music is kinetic and sexually charged, and Elliott and longtime collaborator Timbaland craft some of their most unforgettable and innovative sounds. Everyone loves “Get Ur Freak On,” an instant classic where she spits party raps over a whirling, percussive dervish of drum and bass and Bollywood influences. Just as awesome is “Take Away,” which defines love as a “perfect match” greater than anything the jiggy era could offer. —M.R.

Following the fallout from his infamous interruption of Taylor Swift’s VMA acceptance speech, Kanye West was fighting to win back the public’s favor. That fueled him to do something he hadn’t done before and maybe never will do again: exactly what we wanted him to. MBDTF is an upgraded amalgamation of everything that made us love Kanye: luxurious production, fluid features, and dexterous rapping over themes of grandeur, drugs, sex, and love. It combines the heartfelt vulnerability of The College Dropout, the orchestral soundscapes of Late Registration, the upscaled arena-raps of Graduation, and touches of the Auto-Tuned crooning of 808’s & Heartbreak. Kanye may think differently, but this album is a masterpiece. —M.C.

With narrative development akin to a bestselling novel, Kendrick Lamar’s third album whisks us from Compton to South Africa and back again, with stirring meditations on everything from colorism to incarceration to wealth inequality along the way. Kendrick’s imagination here is deep and deft, as he dreams aloud of resilience, vengeance, and conversations with religious and rap deities. Both the sound and the words of Butterfly gracefully toe the line between diverse and disjunct with producers like Terrace Martin and Sounwave elevating Kendrick’s stories by bending jazz, soul, funk, and psychedelia into the shape of a hip-hop album. —M.C.

The crowning achievement of rap’s greatest year, Nation of Millions was hip-hop’s first masterpiece. Musically, it was Sgt. Pepper’s; lyrically, it was London Calling, a radical mix of controlled chaos, righteous anger, dizzying scratch workouts, and samples that collided like a demolition derby. Chuck D led the prophets of rage with his instantly recognizable stentorian shout, taking aim at radio programmers, the prison-industrial complex, the media, the surveillance state, and addictions to both drugs and TV. The four-man Bomb Squad production team picked only the most caustic and noise-bringing samples. World’s-greatest-hype man Flavor Flav brought the undeniable spotlight-stealing star power that ultimately crossed generations. Louder than a bomb, its influence crossed genre lines from hip-hop to heavy metal to shoegaze and beyond. —C.W.