Entertainment Music Top 50 Rap Songs of the 90s Share PINTEREST Email Print Music Rap & Hip Hop Top Picks Basics Rock Music Pop Music Alternative Music Classical Music Country Music Folk Music Rhythm & Blues World Music Punk Music Heavy Metal Jazz Latin Music Oldies Learn More By Henry Adaso Henry Adaso Henry Adaso has written about hip-hop since 2005 and founded the award-winning blog The Rap Up. He has written for "Vibe," MTV, Rap Rehab, and more. Learn about our Editorial Process Updated on 05/24/19 The 90s represent a romantic era for most hip-hop heads. A strong, inventive, diverse era that stretched the boundaries of hip-hop innovation. Whether you're headed to a 90s themed party or simply pining for nostalgic days, the tunes make a perfect soundtrack. These tunes will take you back to your middle school days. They'll jolt you back to the first time you heard the legendary voices of 2Pac and Biggie. Or the first time you experienced Nas' lyricism, or Scarface's storytelling or Juvenile's rasp, or Master P's grunt or Jay Z's swag. Let's take a trip down memory lane and revisit the best 90s hip-hop songs of all time. 50 of 50 Juvenile - "Ha!" Jemal Countess/Getty Before Lil Wayne. Before Drake. And certainly before Young Thug. There was Juvenile. Cash Money's original flagship artist logged a moment of triumph with "Ha." 49 of 50 Eric B & Rakim - "Don't Sweat the Technique" MCA Records Rakim is just relentlessly rhyming on this thing with such a frenzy that it sounds like he's sprinting away from a Cheetah. The bleak, panicked vibe puts in stark contrast with Ra's typical calm and elegance, which makes it a gripping listen. 48 of 50 Canibus - "Second Round KO" Universal Records Braggadocio is the crux of battle rap. Battle emcees are proficient at hurling verbal insults at rivals directly or subliminally. Canibus best exemplified the artful side of battle rap on "Second Round KO," a shot at LL Cool J. 47 of 50 Kool G Rap & DJ Polo - "Ill Street Blues" Trackmasters Kool G Rap changed the game with his brand of hardcore. It's not that people weren't rhyming about gory stuff pre-G Rap. They were. G Rap simply raised the stakes. He took lyricism to cinematic extremes. On “Ill Street Blues,” for example, he says: "We snatched him by his hands and feet and threw him out the window/Up, up, up and away cause I don’t play, clown/ Buck, buck, buck, take that with you on the way down.” Christ. 46 of 50 AZ - "Sugar Hill" Motown Following his captivating guest appearance on Nas' Illmatic, AZ built his own solo buzz on the strength of this dose of ghetto pop. "Sugar Hill" dominated the airwaves in summer of '95, thus paving way for AZ's debut LP, Doe or Die, in October of the same year. 45 of 50 Gang Starr - "Mass Appeal" Guru & DJ Premier Hard to Earn contained several songs, including this tongue-in-cheek hit, that hinted at the Gang Starr's frustration with the rap scene. Musically, it's as smooth as summer songs go. 44 of 50 Master P - "Make em Say Uhhh" Chelsea Lauren/Getty Images It's a miracle, in retrospect, that Master P earned widespread fame and fortune. He wasn't exactly an exceptional lyricist or producer. Beats and rhymes aren't everything, it turns out. It's a testament to P's tastes that he darted onto the top of the chart with the street classic, "Make 'Em Say Unghh" and made a fortune for (and from) a host of other rappers in his crew. 43 of 50 Akinyele - "Put It in Your Mouth" Steve Eichner/Getty Images "Put It in Your Mouth" is a good sample of the best the 90s had to offer--a variety of one-off rockets, each with a distinct agenda. Public Enemy brought politics. Ice Cube brought rage. Diddy broughg the party. And Akinyele brought...well, fellatio. 42 of 50 De La Soul - "Breakadawn" Paul Natkin/Getty Images When you hear "Breakadawn," the 1993 single from De La Soul's Buhloone Mindstate, the first thing that jumps out at you is the riveting sample. Prince Paul incorporates a mix of live instrumentation and elements from Jackson's "I Can't Help It," taken from Off the Wall. 41 of 50 Scarface - "I Seen a Man Die" Raymond Boyd/Michael Ochs Archives/Getty Scarface has been studied and emulated by almost everyone who came after him, as well as a few contemporaries. Yet, none has ever been mistaken for the deep-voiced Houstonian. To understand why Face commands respect in the game, visit "I Seen a Man Die," where he paints a very vivid picture of fate gone awry. 40 of 50 Brand Nubian - "Slow Down" Brand Nubian at the Canal Room on October 27, 2011. Johnny Nunez/Getty Images "Slow Down" is rife with wisecracks I'd love to put on a T-shirt someday. Sadat X spends his entire verse ridiculing crackheads: "On your crack card you're getting only As and Cs for come back." 39 of 50 ODB - "Brooklyn Zoo" Bob Berg/Getty Images Legend has it that ODB was in an altered mental state and so he didn't know what he was doing when he recorded this Brooklyn-doting smash. Nothing is ever that simple. Whatever the case, the Wu-Tang magician certainly knew how to turn things animated and firmly nailed a call of the wild on "Brooklyn Zoo." Long after his death, ODB fans still chant "Brooklyn Zoo" at concerts in different area codes. 38 of 50 Eric B & Rakim - "Mahogany" David Corio/Getty Images Rakim a true master of emceeing. Not only is he gifted at moving the crowd, he's also one of a handful of MCs capable of making rap both fun and clean at the same time. "Mahogany," a tribute to the ladies, stands the test of time as evidence of Ra's unparalleled greatness in his era. 37 of 50 Raekwon - "Incarcerated Scarfaces" Bob Berg/Getty Images Raekwon's first solo album reminded us that compelling art sometimes comes down to musical genealogy. And Wu-Tang swordsmen knew all the inside secrets. "Incarcerated Scarfaces," an enduring piece from Only Built 4 Cuban Linx, spoke to the streets with eloquence and electricity. 36 of 50 Black Sheep - "The Choice is Yours" Richard Cheese "You can get with this or you can get with that. You can get with this or you can get with that." Contrary to your grandma's belief, those Kia Soul hamsters didn't concoct that famous line. 35 of 50 Craig Mack - "Flava in Ya Ear" Raymond Boyd/Getty Images Hands up if you knew this was a Craig Mack song. B.I.G. spelled trouble for his collaborators when he opened with, "“N---as is mad I get more butt than ash trays." Every word, every syllable, every rhyme oozed excellence, none more memorable than an advice Mack will still find useful two decades later: "Don't be mad, UPS is hiring." 34 of 50 Lauryn Hill - "Doo Wop (That Thing)" Anthony Barboza/Getty Lauryn Hill took us to school on the issue of sexual politics. And it sounded so good. Just one more reason she's widely respected as one of the greats. 33 of 50 Busta Rhymes - "Woo Hah! Got You All in Check" Al Pereira/Michael Ochs Archives/Getty Images Busta and his funky dreads and raspy delivery brought a wave of excitement to 90s hip-hop. Although not a big name at this point in his career, "Woo Ha" and its attention-grabbing hook immediately established Busta as a fan favorite. 32 of 50 Puff Daddy - "It's All About the Benjamins" Scott Gries/Getty Images In 1997, you weren't even considered a real hip-hop fan if you didn't bounce to "It's All About the Benjamins." No one buys Puff's music for the rhymes or storytelling. We buy Puffy for a party, and this one helluva party hit. 31 of 50 Common - "I Used to Love H.E.R." Jamie McCarthy/Getty Images When Common dropped Resurrection in 1994, there was no shortage of great hip-hop albums. Still, he managed to stand out, thanks to songs like "Resurrection" and "I Used to Love H.E.R." Before Common, no one had thought to personify hip-hop. No one thought to assign a gender to it. "I Used to Love H.E.R.," a metaphor for hip-hop's evolution, would go on to prove that Common's skill, purpose, and approach to storytelling was anything but common. 30 of 50 Tha Luniz - "I Got 5 on It" Johnny Louis/Getty Images "I Got 5 On It" was the official anthem for broke fiends everywhere. It's also special for adding a new terminology to hip-hop lingo. 29 of 50 Digital Underground - "I Get Around" Al Pereira/Getty Weekends were made for Michelob" raps Digital Underground's Money B, echoing the vintage beer jingle. Even if you don't give a whit about Michelob or weekend grilling, you'll still enjoy this tune on any day of the week. 28 of 50 Naughty by Nature - "OPP" Slaven Vlasic/Getty Images We spent most of childhood trying to find out what "OPP" stood for. Of course, every adult around lied to me about the true meaning of the acronym - everything from "Other People's Property" to "Other People's Pimples." When I later found out, I felt like a loser. We should have been enjoying this bouncy, call-and-response masterpiece instead. Don't make the same mistake, young Padawan. 27 of 50 Jay Z - "Dead Presidents II" Tim Mosenfelder/Getty Images Jay Z spells out his lofty goals while kicking some of the illest lines he's ever rhymed. 26 of 50 Above the Law - "Black Superman" Ruthless Records Above the Law is one of the most underrated hip-hop outfits ever. Not even Dr. Dre's stamp of approval could lift them above the ground. Still, "Black Superman," a standout from Uncle Sam's Course is one of the highlights of 90s gangsta rap. 25 of 50 2Pac - "Keep Ya Head Up" Steve Eichner/WireImage "Keep Ya Head Up" is arguably 2 Pac's best song ever. Over DJ Daryl's rendition of Zapp & Roger's "Be Alright," Shakur offers a message about staying ahead of the struggle and showing respect to all, regardless of gender. 24 of 50 Wu-Tang Clan - "Protect Ya Neck" Martyn Goodacre/Getty Images The Wu has been bringing da ruckus to gyms since the days of George H. W. Bush. You best protect ya neck, son. 23 of 50 Jazzy Jeff + Fresh Prince - "Summertime" Chris Polk/Getty Images The ultimate summer tune. Back when Fresh Prince rapped about chasing skirts and cruising down the street. Squeaky-clean summer classic, replete with references to two of my favorite things in the world: barbecue and B-ball. 22 of 50 Nas - "Nas is Like" J. Shearer/WireImage "Nas Is Like" is songwriting perfection. Nas spiffs up his nasty flow and makes his word dance in harmony with DJ Pemier's slick composition. A song so good it would fit right in with Illmatic. 21 of 50 The Pharcyde - "Passin' Me By" Mick Hutson/Getty Images This was the soundtrack to my high school days. It was the perfect chill song to offset the high-adrenaline side of the game. Bizarre Ride II The Pharcyde had other wondrous gems ("Otha Fish," for instance), but "Passin' Me By" was the one that directly put me under a spell. 20 of 50 The Lady of Rage - "Afro Puffs" Earl Gibson III/Getty images It's a shame The Lady of Rage didn't explode onto mainstream consciousness. She was a victim of bad timing and even worse company (Death Row). Though we never got to witness her full-range potential (she only dropped one album), you've no doubt heard the undeniably catchy "Afro Puffs." 19 of 50 O.C. - "Time's Up" Jack Vartoogian/Getty Images O.C. (Omar Credle) was to lyricism what Ray Allen was to three-point shots: a specialist. Dig up Word...Life for a widescreen view of O.C.'s poetic provenance. 18 of 50 Juvenile - "Back That Thang Up" Jemal Countess/Getty No one suspected it way back when, but "Back That Thang Up" is now as famliiar as a household item. Like a remote control. And early evidence of the sheer cultural osmosis created by the Cash Money takeover of the late-90s/early-00s. 17 of 50 Snoop Dogg - "Gin & Juice" Rick Kern/Getty images Following 93's "Nuthin' But a G Thang," Snoop teamed up with Dr. Dre for yet another surefire hit in "Gin & Juice," off the critically lauded DoggyStyle. All the splendid elements of west coast g-funk are mashed up in this anthem. 16 of 50 A Tribe Called Quest - "Bonita Applebum" Taylor Hill/Getty Images "Bonita Applebum" was the perfect fusion of nuanced, groove-oriented atmosphere and that whimsical fluidity Tribe fans love. Abstract and smart, but effectively hooky. 15 of 50 OutKast - "Elevators (Me & You)" Paras Griffin/Getty Images "Elevators (Me & You)", among other 90s hits, help loft OutKast into the highest ranks of music duos. Everyone knows this one. Word for word. Even your momma, poppa and grandmama. 14 of 50 Souls of Mischief - "93 Till Infinity" Frazer Harrison/Getty Images Most people can't name the members of S.O.M., but when they hear this song at a party they completely lose it. "93 Till Infinity" was indeed a prophetic title, because the song is still as mesmerizing today as it was decades ago. 13 of 50 Public Enemy - "Welcome to the Terrordome" C Flanigan/Getty Images Public Enemy sparked a revolution on wax at a time when it was considered the risky move. "Welcome to the Terrordome" stretches over five minutes but sounds like a brisk walk. It represents lasting evidence of P.E.'s political edge. It has been reworked by other artists, including Pharoah Monch. 12 of 50 Wu-Tang Clan - "C.R.E.A.M." Never has there been a wildly influential hip-hop song so soothing by a group so blunt as Wu-Tang's "C.R.E.A.M." That, my friends, is the genius of The RZA. 11 of 50 OutKast - "Player's Ball" Chris McKay/Getty Images These two dope boyz in a Cadillac started off on a strong note with Southernplayalisticadillacmuzik. OutKast's first outing worked in part because Big Boi and Andre 3000 redefined most people's perception of southern rap. They created an experience that was far more progressive and, ultimately, familiar. 10 of 50 2Pac - "California Love" Rachel Murray / Getty Images As good a tribute as the more emotive "To Live & Die in LA," "California Love" is one of Tupac's best known works. Dr. Dre's piano-laden production frames the soundbed for a celebratory ode to Cali, while Roger Troutman's vocoder-aided chorus adds some flavor to the mix. 09 of 50 A Tribe Called Quest - "Electric Relaxation" Taylor Hill/Getty Images When we first heard "Electric Relaxation" I didn't understand half the rhymes ("Relax yourself to help you set the lamp?"), but the beats, the flows and the rhythm kidnapped our spirit and turned us into a zombie. We haven't been found since. 08 of 50 Ice Cube - "It Was a Good Day" Taylor Hill/Getty Images A good day in L.A. must have been at a premium when Ice Cube penned this stellar track. The video for "It Was a Good Day" follows Cube through an astonishingly peaceful day in South Central L.A. The song is exactly 4:20 in length, but I'm sure that's a mere coincidence. 07 of 50 Method Man - "I'll Be There for You" Scott Dudelson/Getty Images Method Man and Mary J. Blige balanced grit with warmth, strength with tenderness, and rap with R&B. Mary is Magic. Method is Kareem. Hood love slam dunk at its best. 06 of 50 Pete Rock & C.L. Smooth - "T.R.O.Y. (They Reminisce Over You)" Johnny Nunez/Getty Images Insane horn riffs. Shimmering cymbals. Soulful samples. You just know it's Pete Rock's unmistakable craftsmanship. On the other end, C.L. Smooth channels controlled emotion through the mic on this funeral favorite. This is melancholy elegy at its finest. 05 of 50 Nas - "The World Is Yours" Paras Griffin/Getty Images Nas connected with Pete Rock on this hot rock from Illmatic. The song's message of self-belief is as much a directive to himself as it is to his future seed. "Thinkin' of a word best describin' my life/To name my daughter my strength/My son, the star, will be my resurrection/Born in correction all the wrong sh-t I did/He'll lead a right direction," Nas prays. 04 of 50 Mobb Deep - "Shook Ones II" Brad Barket/Getty Images "I got you stuck off the realness, we be the Infamous, you heard of us" starts Prodigy on Mobb Deep's most enduring track, "Shook Ones II." P's opening lines are menacing and memorable and should be studied in a classroom somewhere. But before his voice enters the room, Havoc puts his nose down and stirrs up the calm before unleashing the full storm with a squeal that builds atop a haunting piano loop. You're hooked from start to finish. 03 of 50 Geto Boys - "Mind's Playing Tricks on Me" Raymond Boyd/Getty Images The brooding paranoia of "Mind Playing Tricks" served as a metaphor for the mental disillusionment that often accompanies inner-city angst. There's no way a song this dark should've made it into heavy rotation. But it did. That "Mind Playin' Tricks on Me" went on to become such a huge success has everything do with Scarface's surrealism, Bushwick Bill's suicidal mindset, and Willie D's stone cold flow. Geto Boys at their best. 02 of 50 Dr. Dre - "Nuthin' But a G Thang" (Ft. Snoop Dogg) Elsa / Getty Images Snoop and Dre drove this Cali anthem all the way to No. 2 on the Billboard Hot 100 charts in 1993. This was the first single from The Chronic and it immediately established him as a supersonic force for decades to come. 01 of 50 The Notorious B.I.G. - "Juicy" Raymond Boyd/Michael Ochs Archives/Getty Images "Juicy" is Biggie's most important song. Period. It has that rare moment of self-introspection. Biggie died three years later, but this song lives on in the through those who remember the days of The Source and Mr. Magic.