The Best 90s Hip Hop Songs: Classic Cuts From A Golden Era

2Pac, Biggie, Nas, Wu-Tang Clan, Missy, Outkast, Dre, Snoop: The 90s were a decade in which hip hop became one of the biggest genres in the world.

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The best 90s hip hop songs are like the best music of any decade of any genre. Expansive, uncategorizable, and powerful. The following list encompasses artists from around the world, transforming the genre irrevocably, and doing it to an audience that got bigger and bigger as the decade went on. By the time the 90s were over, hip hop wasn’t just a genre anymore. It was pop music, its most successful songs regularly crossing over. The list below shows how that all happened, and hopefully provides a few avenues for further discovery.

(Note: We included one song per artist, simply because we wanted to pay tribute to as many artists as possible.)

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Looking to explore some of the best hip-hop songs of the 90s? Check out our exclusive playlist on Spotify.

102: Young Black Teenagers – Tap The Bottle (1993)

Young Black Teenagers released an album in 1993 called Dead Enz Kidz Doin’ Lifetime Bidz. It was an obvious – though plenty powerful – statement on the way Black kids were treated in the United States, and the way mainstream society viewed rappers. But the kids liked to have fun, too. “Tap The Bottle” is a boisterous drinking anthem, buoyed by a chanted chorus and an infectious organ sample; proof that all kids should be allowed to have this much fun.

101: The WhoRidas – Shot Callin’ & Big Ballin’ (1997)

The WhoRidas were Oakland staples, but they found a home on the prosperous LA label, Delicious Vinyl. On the West Coast, they became massive after the release of “Shot Callin’ & Big Ballin’,” which was a far cry from the g-funk dominated radio that had come in the wake of Dr. Dre’s success. The WhoRidas proved that, well, shot callin’ and big ballin’ wasn’t only for the disciples of Dre’s teachings.

100: Rappin’ 4-Tay – Playaz Club (1994)

“Playaz Club” emerged as a g-funk classic, the sort of song that was an immediate appeal but also appeared on compilations collecting West Coast classics long past its release date in the 90s. The song utilizes an excellent sample from Judy Clay and William Bell’s 1968 hit “Private Number,” with a guitar line that effortlessly highlights Rappin’ 4-Tay’s silk voice, equal parts mysterious and confident. Easily one of the best hip hop songs of the 90s.

99: Slick Rick – Street Talkin’ (1999)

By 1999, Slick Rick was 15 years into his lauded career, looking for a final boost for his final LP, The Art of Storytelling. He found that boost in OutKast, who helped turn “Street Talkin’” into a street-ready anthem that instantly introduced OutKast’s young audience to the legendary smooth-talking rhymes of Slick Rick.

98: Heltah Skeltah – Leflaur Leflah Eshkoshka (1995)

Heltah Skeltah has always been credited with “Leflaur Leflah Eshkoshka,” but the song’s chorus lays out all the main players: “Yes yes y’all (yes y’all)/OGC, Heltah Skeltah be the best y’all (best y’all)/Fab 5 slam from East to West y’all.” This is a posse cut in the truest sense of the word, uniting the trio of OGC and the duo of Heltah Skeltah, who together consisted of The Fab 5. They were all united alongside a few other groups under the name Boot Camp Clik, meaning Heltah Skeltah rep a number of connected crews on the hit.

97: WC and the Maad Circle – West Up! (1995)

A year before WC left the Maad Circle to form Westside Connection with Ice Cube, he invited the MC to appear on his group’s song “West Up!” The track eschews the g-funk of the era in favor of soulful keyboard chords and a bevy of back-and-forth verses that finds each MC waxing poetically on the merits of the West Coast sunshine.

96: 3X Krazy – Keep It On The Real (1997)

3X Krazy didn’t really hide their intentions with their hit “Keep It On The Real,” a standout hit from Keep It On The Real. Foreshadowing the hyphy era of hyper stylized vocal performances in the late 90s Bay Area, the song is an unabashed West Coast classic, and considering that’s exactly what 3X Krazy set out to do with “Keep It On The Real,” it’s mission accomplished.

95: Mack 10 – Foe Life (1995)

On “Foe Life,” Mack 10 humorously pits himself against the “yes yes y’all” call-and-responses of East Coast hip hop. At first, Mack and (guest artist and producer) Ice Cube chant about being the best MCs out, before Mack interrupts and says, “Wait a minute, that ain’t how the West Coast rock!” The song shifts beats, and “Foe Life” emerges as a g-funk banger, the antithesis to the glossy beats and easy boom-bap of East Coast hip hop. Mack 10 and Ice Cube drew a line in the sand with this song, one that was permanent in the 90s hip hop scene.

94: The Dove Shack – Summertime In The LBC (1995)

C-Knight, Bo-Roc, and 2Scoops were clear Warren G disciples. They made their debut on his seminal album, Regulate…G Funk Era, but on “Summertime In The LBC” they stand out on their own. Even though they admit to running with Warren G, the sultry vocals, delightful harmonies, and smooth funk bassline gives the song a perfect summertime feel. It’s a song extremely of its era, but quirky enough to live on to inspire new generations of R&B songwriters.

93: The B.U.M.S – Elevation (Free My Mind) (1995)

The Bay Area B.U.M.S, also known as Brothas Unda Madness, had a penchant for throwing the kitchen sink into their raps. The duo, alongside frequent producer Joe Quixx, relied on lush samples and an R&B influence to subvert traditional West Coast g-funk and hardcore hip hop. The chorus, a simple call to “Free My Mind,” foreshadowed the heady, mindful approach many California MCs would rely on in the future.

92: Low Profile – Pay Ya Dues (1990)

Low Profile’s “Pay Ya Dues” was just barely released in the 90s, but its appeal lies in the fact that it mines similar territory to so many songs on this list. Over a beat that sounds like a cassette recording of Prince’s drums, rapper W.C. spits about MCs looking for success without paying their dues, trying to cut the line to make a quick buck. The beat he raps over would fall out of fashion by the early 90s (and return in the mid-2000s), but the ethos and spirit of the groove and subject matter still live on.

91: Wreckx-N-Effect – Rump Shaker (1992)

If the Harlem-bred New jack swing group Wreckx-N-Effect released the video for “Rump Shaker” in the 2020s, it’d be no big deal. But the bikini-clad party-goers they showcased in the 1992 video for “Rump Shaker” were so provocative upon release, that MTV – the edgiest of networks in the 90s – banned the hip hop song from their airwaves. Wreckx-N-Effect member Markell Riley recruited his brother, Teddy, for a verse, who notably asked a young Pharrell Williams to help with his bars.

90: Erule – Listen Up (1994)

As a midwestern bred MC, Windy City rapper Erule blended aspects of classic 90s East Coast and West Coast hip hop into an eclectic style infused with his own charisma. On the song “Listen Up,” he plays with classic loops, funk samples, and an eerie synth floating above the entire beat that recalls the early days of Memphis’ horrorcore style. In Erule’s hands, though, these disparate styles fuse effortlessly.

89: MC Solaar – Caroline (1991)

Few MCs have introduced a generation to a new style of music like MC Solaar did for aspiring musicians in Paris. He came up in the early 90s and broke through with “Caroline,” a sultry love jam that immediately established Solaar as both a highly skilled rapper and a romantic. Rumors have swirled as to who, exactly, Caroline was, but like his UK counterpart MF DOOM, MC Solaar realized that some things are better left as mysteries.

88: Showbiz & AG – Next Level (Nyte Time Mix) (1995)

No offense to Showbiz, but re-upping “Next Level” with a “Nyte Time” remix courtesy of DJ Premier turned out to be a good choice. The original was nice, but Premier’s beat, which sampled Maynard Feguson’s “Mister Mellow,” became a sensation. Of course, it helped that Eminem’s character in 8 Mile rapped over the beat during his first professional freestyle.

87: DJ Vadim – The Next Shit (1995)

Though DJ Vadim is widely celebrated as the hip hop voice to emerge from the Soviet Bloc in the 80s, he got his hip hop education in England, where he moved as a young kid. Over a lurching, pitched-down beat that sounds like it could have emerged out of the chopped-n-screwed era, Vadim lays down a beautiful instrumental on “The Next Shit.” It’s the sort of song that illustrates how far hip hop traveled in the 90s, and how artists like Vadim helped usher in the beat scene renaissance of the early 2000s.

86: Lost Boyz – Renee (1996)

“Ghetto love is the law that we live by.” That’s the motto of Lost Boyz’s hit single “Renee,” a heartbreaking track that too accurately mirrors the struggles of trying to escape the hood. The song tells the story of a young man who falls in love with a young girl in law school, Renee, who gets shot to death in a botched home invasion robbery. It became a massive hit thanks to its unflinching eye towards the violence that plagues neglected communities, without ever glorifying said violence.

85: Diamond & The Psychotic Neurotics – Best Kept Secret (1992)

Diamond D, the genius behind “Best Kept Secret,” knew the secret to all great hip hop music: surround yourself with brilliant friends. That’s precisely what he did on “Best Kept Secret,” which features a beat he cooked up himself and verses from Bonita, Fat Joe, LaReese, and Whiz One. Of course, It’s Diamond who comes through with the iconic opening bar: “Ya see I skip to my loo like Napoleon at Waterloo/My name is Diamond D, tell ya what I’m gonna do/I dip and I dab like a Mike Tyson jab/Even though there’s flab I possess the gift of gab.”

84: 3rd Bass – Pop Goes The Weasel (1991)

3rd Bass didn’t really hide who they were talking about when they came for heads on “Pop Goes The Weasel.” MC Serch raps, “I guess it’s the fact that you can’t be artistic/Intricate raps, becomin’ so simplistic/I gotta strong mind, it doesn’t have to be spoon-fed/And I can read what doesn’t have to be read.” The song was aimed at commercial acts like Vanilla Ice and MC Hammer, and with “Pop Goes The Weasel,” they proved that intricate, high-brow songs could perform commercially and artistically.

83: Da King & I – Tears (1993)

Da King & I’s “Tears” has plenty of monumental moments, but few songs begin with a better four bar lyric than this one. Izzy Ice raps, “Sitting on my doorstep, thinking with my head down/Alone in my own world with no one left around/Then out of nowhere comes my partner Majesty, asking me/’Yo, Izz why you look like there’s been a tragedy?” Izzy replies to DJ Majesty that he saw his crush hitting on a “light skinned boy,” and the image would become a lasting relic of 90s hip hop.

82: Channel Live – Mad Izm (1995)

“Mad Izm” quickly established Channel Live as the most exciting group from New Jersey outside of The Fugees. The song, featured on the group’s debut Station Identification, is classic 90s boom-bap hip hop, produced by legendary Boogie Down affiliate KRS-One, who also chipped in a featured verse. The duo, alongside KRS, muse on the magic of the “Izm,” a sort of mystical power that imbues the members with the inability to outrap any wack MC.

81: Freestyle Fellowship – Inner City Boundaries (1993)

With Innercity Griots, and its jazz-heavy standout, “Innercity Boundaries,” Freestyle Fellowship established themselves as an avant-garde alternative to traditional LA hip hop. The group’s members were part of the massively influential Project Blowed collective, which blended highly technical rap skills (see: Myka 9 and Daddy-O in verse two) with the presence of Leimert Park’s jazz scene. With this formula, Freestyle Fellowship helped establish a new underground in West Coast hip hop.

80: Boss – Deeper (1993)

Calling yourself the Boss takes serious swagger, but then again, you had to come with twice as much talent to be welcomed into the boys club of 90s hip hop as a hard spitting female MC. Boss was exactly that, with an endless fountain of charisma and bars that would make Shakespeare jealous. The Michigan MC’s “Deeper” ended up being one of the bigger Def Jam hits of the mid-90s, anchored by her ferocious flow and relentless energy.

79: Westside Connection – Bow Down (1996)

Westside Connection was a West Coast supergroup set up to rival Dr. Dre and Snoop Dogg’s magnetic collaboration. The group, consisting of Mack 10, WC, and Ice Cube, became a California sensation thanks in large part to “Bow Down,” a celebratory tour de force from the group that cemented their place as both individual stars and as a collective triumph. The group went after all enemies – real and imagined – which included Cypress Hill and Common.

78: Group Home – Livin’ Proof (1995)

Group Home put their title to use on albums like Livin’ Proof, which features production from Gang Starr and Big Jaz. The project also includes guest appearances from Absaloot, Big Shug, Guru, Jeru the Damaja, Jack the Ripper, and Smiley the Ghetto Child. The title track features a simple boom-bap beat with a barely-there synth melody that allows each member to riff on life in New York. It’s a classic Golden Age hip hop song, transcendent of any era, while still looking specifically at life in the 90s.

77: Nikki D – Daddy’s Little Girl (1991)

Nikki D is rightfully celebrated as the first woman of Def Jam. Her album, also titled Daddy’s Little Girl, was the first record the label put out by a female hip hop artist, and Nikki more than delivered. Playing with R&B, soul, and rap, Nikki immediately introduced the Def Jam audience to a new side of the industry. On the lead single she spits over lush strings and outlines the balance between portraying who people expected her to be while standing out from her pack.

76: Ed O.G.& The Bulldogs – I Got To Have It (1991)

Boston wasn’t considered much of a hip hop hotbed in the early 90s, and while the city was slow to embrace any sort of scene, Ed O.G. was paving the way as a pioneer. “I Got To Have It,” his biggest unimpeachable hit, begins with a dusty groove before Ed kicks the crackly sample to the curb and spits over clean drums and a simple loop O.G. is a rare MC that is comfortable rapping over minimal beats, moving from demeaning his enemies’…manhood in one verse, before pleading for Black unity in the next. Ed O.G. truly brought it all on “I Got To Have It.”

75: AZ – Sugar Hill (1995)

For AZ, heaven isn’t the afterlife, it’s the ease of mind that comes after finally being able to retire from the streets. It’s an imagined paradise where slinging drugs to pay the bills is a lifetime away, and the only day-to-day chores for the MC include smoking cigars and hanging out with ladies. AZ was one of the most imaginative lyricists of the 90s, and on “Sugar Hill” he paints a world that’s impossible not to envy, though the struggle to get there is one few could persevere.

74: Ganksta N-I-P – Psycho (1992)

Ganksta N-I-P’s music, especially songs like “Psycho,” were instrumental on multiple levels. First, N-I-P was a relentless supporter of his hometown of South Park in Houston, Texas. Plus, N-I-P’s visceral, violent, unflinching lyrics would help usher in the horrorcore era of hip hop made famous by other Southern acts like Three 6 Mafia. “Psycho” was too rough for some ears, but it inspired a generation of rappers pissed off at the status quo.

73: Mic Geronimo – Masta IC (1995)

Mic Geronimo got his start as a high schooler in Queens as a loose associate of Irv Gotti from Murder Inc. Despite these connections, it was always clear that Geronimo was going to be a star; he was simply too nice on the mic. “Masta IC” is a seminal example of his smooth delivery and ability to coast over perfectly grooving boom-bap beats. When he raps, “I be getting money ‘til the day that I die,” you believe him.

72: The Nonce – Mix Tapes (1995)

The Nonce were one of the first groups to make headway out of the Project Blowed scene in Leimert Park. The duo had a penchant for simple beats and rhymes that would pay homage to the artistry of hip hop. “Mixtapes” charts this rise, from the early days slinging mixtapes before traveling from freestyle cipher to freestyle cipher in hopes of making it big. Eventually, they did.

71: Grand Daddy IU – Something New (1990)

Grand Daddy IU was as much of a character as he was an MC, which would in turn inspire a whole generation of rappers to place importance on stylistic tics, trademarks, and signature deliveries. But IU could also rap his ass off, like he did on “Something New,” which was one of the reasons why Biz Markie signed up to produce his music. Though the two would sour towards each other, Grand Daddy’s look of a suit and tie helped create a world of possibilities for rappers following in his footsteps.

70: Heavy D & The Boyz – Now That We Found Love (1991)

Heavy D was known for more than being played in the limousine Biggie rode around in during “Juicy.” That’s due, at least in part, to the monumental success of “Now That We Found Love.” And while “Now That We Found Love” is technically a dance track, Heavy D’s delightful bars firmly cement the song into crossover territory. Add in Teddy Riley’s excellent production and the group created a song ready for the dance club and the strip club.

69: Mase – Feel So Good (1997)

Mase’s “Feel So Good” is a helluva debut single. It was released in October 1997 off of Harlem World, and it appeared on the Money Talks soundtrack. The song was produced by D-Dot and P. Diddy, and featured R&B superstar Kelly Price on the chorus. The beat was as maximal as beats came in the mid-90s, with a horn section fit for a king intro’ing the song, before Mase smoothly slides over a funk guitar riff sampled from Kool & The Gang’s “Hollywood Swinging.”

68: House of Pain – Jump Around (1992)

If at first you don’t succeed, try and try again. DJ Muggs, who produced this classic 90s hip hop song, stated that he originally made the beat for Cypress Hill, but rapper B-Real did not want to record at that time. It was then offered to Ice Cube, who refused it, before he finally took it to House of Pain who turned the instrumental into a massive hit. B-Real made right on his oversight, though, eventually using the beat for a Cypress Hill song, “Insane in the Brain.”

67: Ras Kass – Ghetto Fabulous (1998)

The West Coast hip hop universe gravitated around Ras Kass’ mega hit “Ghetto Fabulous.” The song was produced by Stu-B-Doo and featured a guest verse from Dr. Dre. The b-side featured Xzibit, and Ice-T made a cameo in the video. It was one of those excellent songs that showcased the unity and close ties of California’s expansive gangsta rap scene.

66: Company Flow – Eight Steps To Perfection

El-P has helped change rap a number of times. Before he was running the jewels, though, he, alongside Bigg Jus and Mr. Len, helped usher in an underground rap renaissance with Company Flow. First on Rawkus Records, and then on his own Def Jux label, El and Company Flow married the grittiness of traditional NYC rap with a thrilling new POV on tracks like “Eight Steps To Perfection.” The track features a beat that would make a skeleton nod its head and slick verses from both Jus and El.

65: Jeru The Damaja – Come Clean (1993)

Before he was Jeru the Damaja, Kendrick Jeru Davis was a high schooler with an aspiring hip hop career, alongside his two friends who would grow up to be Guru and DJ Premier of Gang Starr. While Jeru took advantage of this affiliation (“Come Clean” was produced by Premier), he worked hard to establish himself as a solo star, and “Come Clean,” the centerpiece of his masterpiece, The Sun Rises in The East, remains a Golden Age classic.

64: EPMD – Crossover (1992)

“Crossover” takes aim at all the wack MCs who try to go commercial, which was the dividing line between the underground and mainstream before the division was blurred entirely. Where you stood mattered. The song’s lyrics criticize rappers who crossover to R&B or pop in order to sell more. The song samples “Don’t Worry If There’s a Hell Below (We’re All Gonna Go)” by Curtis Mayfield and Roger Troutman’s “You Should Be Mine.” EPMD’s Erick Sermon and Parrish Smith can make hits without begging for radio play.

63: MC Hammer – U Can’t Touch This (1990)

U Can’t Touch This” comes with an award shelf all to its own. The song won Best R&B Song and a Best Rap Solo Performance and the first hip hop song to be nominated for Record of the Year at the 33rd Annual Grammy Awards in 1991. It also received trophies for Best Rap Video and Best Dance Video at the 1990 MTV Video Music Awards.

62: Nice & Smooth – Sometimes I Rhyme Slow (1991)

Nice & Smooth’s “Sometimes I Rhyme Slow” likely would have been a hit without the guitar line and melody they took from Tracy Chapman’s “Fast Car,” but it certainly didn’t hurt the chances of the song becoming a smash. What took this 90s hip hop classic to the next level was the duo’s slick bars, each member jumping between cadences and flow patterns with ease.

61: Scarface – I Seen a Man Die (1994)

On Scarface’s world-beating breakthrough, The Diary, his blend of g-funk and horrorcore helped accent his often remorseless lyrics about the violence he grew up surrounded by. But on “I Seen a Man Die,” he tells the story of a man released from jail, looking for a better life but unable to escape the trappings of the post-carceral system. It’s a tale that plagues too many Black males in this country, and on “I Seen a Man Die,” Scarface brings it to a wide audience.

60: Jurassic 5 – Concrete Schoolyard (1998)

With the release of their debut EP, Jurassic 5 issued a statement: “”I urge every independent artist to put something out first. Prove yourself to yourself, to people that pick up the records, then the [labels] will come looking for you. If they know that you can score, they gonna pass the ball to you.” Jurassic 5 proved this on “Concrete Schoolyard,” a song that helped earn them an Interscope deal. But on tracks like this, they kept their independent ethos and spirit, focusing on “conscious raps” and tales of inspiration and struggle without embellishment.

59: Dr. Octagon – Blue Flowers (1996)

Kool Keith has been a visionary rapper since his early days as a surrealist spitter in the Bronx, but he became another force altogether when he conceived his Dr. Octagon persona and began working with producer Dan The Automator. On songs like “Blue Flowers,” Keith turns into a new MC entirely, creating an all-consuming alter-ego. It began a trend in hip hop that would permeate from underground legends like MF DOOM to mainstream superstars like Lil Wayne, who would assume form as a martian.

58: Positive K – I Got A Man (1992)

Positive K made a bold move in creating “I Got A Man.” The Bronx-bred MC decided to show a courtship from both the male and female relationship, with the man repeatedly asking the woman out, with the woman constantly turning down his efforts because she was in a relationship. But Positive K took it a step further, pitch-shifting his vocals to play both parts.

57: Ja Rule – Holla Holla (1999)

When Ja Rule turned in his major label debut, Def Jam couldn’t peg a particular hit, so they asked him to re-enter the studio and flesh out what would become Venni Vetti Vecci with some new songs. During those new sessions, Ja churned out “Holla Holla,” which would become one of his biggest tracks upon its release. On the track, Ja employs a stutter flow, allowing certain words to take on emphasized meaning, which would become employed by many a hip hop star in his wake.

56: Foxy Brown – Get Me Home (1996)

On “Get Me Home,” Foxy Brown showcased her many sides. With a chorus from Blackstreet, a heavily vocoded harmony, and raunchy verses about getting her flirt on from the high post of the bar, the track fired on all cylinders. Foxy had a close relationship with Jay-Z, who served as a co-writer on the song, and his faith in her talent is well warranted. Foxy established herself as a versatile superstar on tracks like “Get Me Home,” seamlessly blending her raps into R&B melodies and New Jack swing-inspired instrumentals.

55: Bone Thugs N Harmony – 1st of tha Month

The 1st of the month, which the Cleveland, Ohio R&B-rap crossover act celebrates, signifies the day welfare checks come in from the government. The song was such a hit as both a catchy anthem and a subtle parody, that Chris Rock dubbed it a “welfare carol” in one of his specials.

54: Arrested Development – People Everyday (1992)

For newcomers to hip hop in the 90s, Arrested Development’s “People Everyday” introduced audiences to the wonders of sampling. The group re-arranged Sly & The Family Stone’s “Everyday People” in an entirely unique and updated way, illustrating that hip hop at its best was in conversation with Black music of past generations.

53: NWA – Alwayz Into Somethin’ (1991)

“Always Into Somethin’” is an early example of G-funk production helmed by Dr. Dre. MC Ren also includes a diss of Ice Cube, who left the group before the song due to a royalties dispute, beginning a feud that would only escalate. The song became enshrined in California hip hop lore when it was featured in Grand Theft Auto: San Andreas, on the West Coast gangsta rap station, Radio Los Santos.

52: Public Enemy – 911 Is A Joke (1990)

Public Enemy’s “911 Is A Joke” is one of the rare songs from the classic hip hop group that features only one vocalist. Flava Flav handles all the verses on the song, which has become a rallying cry once again in the 2020s as the United States grapples with the crisis of how police treat, and disproportionately kill, people of color.

51: Onyx – Slam (1993)

“Slam” introduced slam dancing to hip hop, but the song has become celebrated for its prevalence in rap culture in the following years. The song was sampled by more than 25 rap artists including GZA, Eminem, PMD, Shaquille O’Neal, and Krazy Drayz of Das EFX. The song has been used in movies such as How High, as well as in numerous commercials for companies like Nike, ESPN, and Gatorade.

50: Digital Underground – The Humpty Dance (1990)

Shock G was early to the alter-ego game. In 1990, he performed the now-classic “Humpty Dance” under his Humpty Humpty alias, and the song lays out the ways in which swagger and charisma can go a long way in meeting ladies. “I’m about to ruin the image and the style that you’re used to,” Shock raps during the opening bar, an announcement that hip hop was about to get a helluva lot funkier, a mission Shock G embarked upon until he tragically passed away in 2021.

49: Bahamadia – Uknowhowwedu (1995)

On “Uknowhowwedu,” Bahamadia proved that women could more than hold their own against the Golden Age heroes of hip hop’s gilded era. The Philly-born artist brought her own spin to a boom-bap style of hip hop that had been birthed in New York, infusing her bars with a slick flow on “Uknowhowwedu” that was mimicked by boys and girls alike on schoolyards across the country.

48: Lords of the Underground – Chief Rocka (1993)

“Chief Rocka” was an immediate 90s hip hop hit thanks to the one-of-a-kind flow of Mr. Funkee and the interplay of his bandmates, DJ Lord Jazz and DoltAll. The song was produced and featured scratches by K-Def, with K-Def and Marley Marl mixing it. The line “I live for the funk, I die for the funk” was sampled for the hook of The Notorious B.I.G. song “Machine Gun Funk,” while “Chief Rocka” was in turn interpolated by Kanye West on “Guilt Trip” from his album Yeezus.

47: Luniz – I Got 5 On It (1995)

In Oakland, it was hard to get as big as Luniz did in the mid-90s. The Bay Area duo achieved massive success with their song “I Got 5 On It,” which chronicled the story as old as time of two dudes chipping in five bucks each to get a bag of weed. Alongside the grass, the duo head to the convenience store to grab some Tanqueray, a bit of wine, an Arizona iced tea or two, and, of course, some blunt wraps for the weed. Never has a normal Friday night sounded so extraordinary.

46: Main Source – Live At The Barbeque (1991)

Before he released his debut masterpiece, Illmatic, in 1994, Nas hinted at his prodigious talent on the wildly fun Main Source anthem “Live At The Barbeque.” You can practically catch a wasp of the ribs sizzling on the grill when the cymbal-heavy drum beat emerges at the beginning of the song. While Nas would go on to become more famous than the members of Main Source, listening to “Live At The Barbeque” is a good reminder that at his peak, Large Pro was one of the best MCs in New York.

45: The LOX – Money, Power, and Respect (1998)

The LOX packed as much talent into “Money, Power, and Respect” as humanly possible. Not only did the group consist of Sheek Louch, Styles P, and Jadakiss, but they recruited Lil Kim for the chorus and snagged a verse from DMX. It was a New York City power play, and it firmly established The LOX as one of the most impressive groups in the city, and worthy co-stars alongside DMX in the Ruff Ryders hierarchy.

44: Ol’ Dirty Bastard – Shimmy Shimmy Ya (1995)

“Shimmy Shimmy Ya” features one of the most iconic beats in the history of hip hop. Produced by RZA, the song begins with a piano line that even the most tone-deaf amateurs can play. The drums come in heavily, and Ol Dirty Bastard’s iconic chorus gives the track an immediate hook to latch onto.

43: O.C. – Times Up (1994)

Though it ended up being a massive moment in New York 90s hip hop, “Time’s Up” was never meant for O.C. The beat was initially a record for Pharoahe Monch from Organized Konfusion. Nas was supposed to be on the record, too, but he never showed up for his recording session. Regardless of the false starts and missteps, though, O.C. turned in a legendary performance on his (solo) cut, “Time’s Up.”

42: Black Sheep – The Choice Is Yours (Revisited) (1991)

“The Choice Is Yours (Revisited),” from the Native Tongues affiliate Black Sheep, was pegged as the second single from their classic debut album A Wolf in Sheep’s Clothing. The song is a masterclass in hip hop sampling, featuring bits from “Keep on Doin’ It” by New Birth, “Her Favorite Style” by Iron Butterfly, “Big Sur Suite” by Johnny Hammond Smith, “Impressions” by McCoy Tyner, and “I’d Say It Again” by Sweet Linda Divine.

41: Souls of Mischief – 93 ’til Infinity (1993)

It’s hard to imagine A-Plus knew exactly what would happen when he made the “93 ‘til Infinity” beat for Souls of Mischief, but it has since become one of the most referenced and recognizable grooves in hip hop history. From there, the group made sure not to miss. They provided a psychedelic, heady West Coast alternative to g-funk excess, instead opting for stories of late-night weed sessions and fighting off the ennui of daily life.

40: LL Cool J – Mama Said Knock You Out (1991)

Before “Mama Said Knock You Out” was released, many people felt that LL Cool J‘s career was on the decline; his grandmother, who still believed in his talent, told him to “knock out” all his critics. Hence the iconic opening line: “Don’t call it a comeback/I been here for years.” The single eventually reached No.17 on the Billboard charts.

39: Ghostface Killah – All That I Got Is You (1996)

Ghostface Killah’s song “All That I Got Is You,” is one of the most stellar debut tracks in 90s hip hop. The song features R&B singer Mary J. Blige and an outro which has Popa Wu giving teachings. The track contains a sample of “Maybe Tomorrow” by The Jackson 5, but it’s the meat of Ghostface’s verses that make “All That I Got Is You,” an ode that balances the trauma of growing up broke while still honoring the person who kept him alive, his mother.

38: Lil Kim – No Time (1996)

It’s hard to outshine the World Trade Center, but Lil Kim – an absolute hip hop icon in the 90s – found a way. In the video for her hit debut single, “No Time,” Kim and Puff Daddy ride up and down escalators in the famed towers, with Kim rapping with the swagger and confidence of a veteran MC. Puff also hopped on the song with Kim, in addition to co-handling production, beginning a relationship that would go on to be one of the most important in hip hop.

37: Cypress Hill – Insane In The Brain (1993)

DJ Muggs had just finished producing House of Pain’s “Jump Around,” when he decided he’d adopt the beat with minimal tweaks for his hip hop group alongside B-Real and Sen Dog, Cypress Hill. B-Real and Sen were talented enough to give the song its own weird, psychedelic energy, which would become a calling card for the group throughout their storied history.

36: DJ Shadow – Midnight In A Perfect World (1996)

DJ Shadow helped turn mixing and sample culture from an underground phenomenon to a bonafide subgenre of hip-hop on its own. In the abstract, rap is the blend of beat and vocals, but on “Midnight in a Perfect World,” Shadow shows how perfect sample cues and meticulously sequenced drums can carry their own emotions without the need for a unique human voice. Shadow’s one-of-a-kind approach to beatmaking helped usher in a new era of beatmaking, while also changing the way many rappers approached production.

35: Ice Cube – It Was a Good Day (1992)

Ice Cube’s “It Was a Good Day” became such a hit that users on the internet actually figured out the exact day he was talking about. The song, he explained, was inspired by… “my life at the time … I was in a good frame of mind. And I remember thinking, ‘Okay, there’s been the riots, people know I will deal with that. That’s a given. But I rap all this gangsta stuff – what about all the good days I had?’”

34: Master P – Make ‘Em Say Uhh! (1998)

“Make ‘Em Say Uhh!,” produced by KLC, featured performers Fiend, Silkk The Shocker, Mia X and Mystikal. It was released during the absolute peak of the No Limit era, during which every album they released turned gold. P recruited much of his team to hop on “Make ‘Em Say Uhh!,” and promptly proved why he was the boss, turning in one of the best songs of one of the most productive eras of hip hop.

33: Eric B. & Rakim – Don’t Sweat the Technique (1992)

Eric B. & Rakim’s “Don’t Sweat the Technique” off their album of the same name was the album’s third single but proved to be the project’s lasting hit. Its longevity is due in part to its role in popular culture, including a feature in the 2011 Matthew McConaughey vehicle, The Lincoln Lawyer.

32: Naughty By Nature – O.P.P. (1991)

Naughty By Nature managed to sample Jackson 5’s “A.B.C.” and pen a hook that was even catchier than the original. The song became so popular that “Down with O.P.P.” became slang across the country, even making its way to the suburbs. The call and response chorus was as infectious as it was brilliant, the sort of simple yet subtly brilliant concoction that vaulted a raunchy group like Naughty By Nature into the mainstream eye.

31: Method Man – Bring the Pain (1994)

Comedian Chris Rock loved Method Man’s “Bring the Pain” so much that he named his 1996 tour and television special after the song. (Meth is credited in the special’s closing credits.) It was the world’s introduction to Method Man’s debut album solo Tical, proof that he was far more than just a member of Wu-Tang Clan.

30: De La Soul – Ego Trippin’ (Part Two) (1994)

De La Soul rarely, if ever, made a bad song, but “Ego Trippin’ (Part Two)” is as culturally important for its message as it is for any sort of musical excellence. The song (and its music video) were an attack on gangsta rap culture. The video caught the attention of rappers such as Ice Cube and 2Pac, who took exception to the video showing a rapper splashing around in a pool similar to a scene in Shakur’s own video “I Get Around.”

29: Jay-Z – Hard Knock Life (Ghetto Anthem) (1998)

It may seem novel now, but Jay-Z grabbing a sample from the Broadway hit Annie was a huge surprise, especially for an artist who had made a name for himself as a stone cold hustler. His peers, like Puff Daddy, turned to 80s pop hits to sample from, but Jay-Z hinted at his innovative maneuverings on the song, mining unexpected territory to bolster his brilliant raps and undeniable charisma.

28: Digable Planets – Rebirth of Slick (Cool Like Dat) (1992)

Though “Rebirth of Slick (Cool Like Dat)” is the only song that truly moved the commercial needle for Digable Planets, hip hop aficionados rightfully celebrate their body of work for effortlessly illustrating the DNA that rap and jazz shared. Featuring a bassline sampled from Art Blakey’s “Stretching,” MC Ish “Butterfly” Butler begins the song with one of 90s hip hop’s most iconic first bars: “We like the breeze flow straight out of our lids/Them they got moved by these hard-rock Brooklyn kids.”

27: Raekwon – Ice Cream (1995)

“Ice Cream,” from Raekwon’s classic solo album Only Built 4 Cuban Linx, features a host of Wu-Tang Clan members, even though it’s a solo track from Rae. It features Method Man in the intro, chorus and outro, Ghostface Killah in the first verse, and Cappadonna in the third, though none of them are officially credited on the song. Together, they helped establish Raekwon’s solo debut as one of the best hip hop albums of the 90s.

26: Busta Rhymes – Put Your Hands Where My Eyes Could See (1997)

Busta Rhymes tapped into the Hype Williams music video phenomenon to help bolster his magnificent single, “Put Your Hands Where My Eyes Could See.” Helmed by Williams and designed by Ron Norsworthy, the video is based on Eddie Murphy’s 1988 film Coming to America, which was playing on the studio television while they originally recorded the song.

25: Common – I Used To Love H.E.R. (1994)

Common likely knew there would be backlash to his single, “I Used To Love H.E.R.,” but it’s hard to imagine he predicted it would start a feud with Ice Cube. Common used “H.E.R.” as an extended acronym for “hip hop in its Essence is Real,” and throughout the song he attacks what he viewed as retrograde politics in 90s mainstream hip hop. Cube thought Common was missing the point, but the song became a watershed moment for the conscious rap movement.

24: Hot Boys – We On Fire (1999)

The Hot Boys were more than a supergroup. They were proof that there was music happening outside of New York and LA, that, as Andre 3000 said a few years earlier, the South had something to say. On “We On Fire,” and throughout Guerrilla Warfare, Juvenile, B.G., Turk, and Lil Wayne have a nearly psychic ability to feed off each others’ bars, a strength that propelled them to the kings of the South, and across the nation, too.

23: The Pharcyde – Passin’ Me By (1993)

Aside from the fact that “Passin’ Me By” is a producer’s paradise – it utilizes samples from “Summer in the City” by Quincy Jones, “125th Street Congress” by Weather Report, and “Are You Experienced?” by The Jimi Hendrix Experience – it also captures a feeling all of us have. A 90s hip hop classic, sure, but also timeless: The song finds each member recounting a schoolkid crush and the pain of those feelings being unrequited. It’s a hopeless sort of pain, but the South Central LA group manage to translate those feelings into triumph.

22: Beastie Boys – Sabotage (1994)

Look, the Beastie Boys’ “Sabotage” is an excellent track, there’s no denying that. But the tune became a 90s hip hop classic thanks to the iconic music video they released for the song, one that has gone down as one of the best videos in the history of the medium. The video, directed by Spike Jonze, captures the joyful chaos the group brought to their music, riffing off 70s cops shows like Starsky & Hutch and Hawaii 5-0. Actress Amy Poehler even said, “There would be no Anchorman, no Wes Anderson, no Lonely Island, and no channel called Adult Swim if this video did not exist.”

21: Mos Def – Ms. Fat Booty (1999)

Mos Def’s “Ms. Fat Booty” is a standout single from the excellent Rawkus Records discography, one of the best runs of any 90s hip hop label. The song was produced by classic NYC producer, Ayatollah. The song and its chorus are both driven by multiple samples of Aretha Franklin’s “One Step Ahead,” a rare single released in 1965.

20. Geto Boys – Mind Playing Tricks On Me (1991)

In the history of rap, gangsters have been glorified, and the hustlers on the streets parlay personal histories into multi-million dollar contracts. With “Mind Playing Tricks On Me,” 5th Ward Houston legends Geto Boys turned that trope on its head, revealing the PTSD, trauma, and horror that comes with surviving poverty in the ghetto. Scarface raps, “Day by day it’s more impossible to cope/I feel like I’m the one that’s doin’ dope/Can’t keep a steady hand, because I’m nervous/Every Sunday morning I’m in service/Prayin’ for forgiveness/And tryin’ to find an exit out the business.” The song is a brutal reminder that the things that rappers talk about are stories they can’t forget.

19: DMX – Party Up (1999)

DMX’s “Party Up (Up In Here)” was, and remains, such a classic song, that the Philly faithful embraced one of their own and brought him into the world of the Eagles. The 90s hip hop anthem is played every time the Philadelphia Eagles score a touchdown. There is perhaps nothing more precious in the City of Brotherly Love than the Philadelphia Eagles, and for them to celebrate every TD with a New York anthem, shows just how monumental DMX’s hit was.

18: The Roots – You Got Me (1999)

There’s something about the crack of Questlove’s snare, the precision of his bass drum, and the crispness of his hi-hats on “You Got Me” that are one-of-a-kind. It could convince the purest digital natives that live drums are the only way to go, because beneath Black Thought’s tale of a blooming romance, Quest’s beat works to perfection. It’s a standout moment from a group with hundreds of them, buoyed by Erykah Badu’s electric performance as Black Thought’s counterpart.

17: Black Star – Definition (1998)

Black Star, which consisted of Mos Def and Talib Kweli, were a case study in underground stars breaking through to the mainstream, and doing so with subject matter that subverted typical hip hop. “Definition” was a plea for rappers to stop promoting violence, and the song found such a wide audience that it helped bolster Rawkus Records to the top of the indie darlings of late 90s hip hop.

16: Juvenile – Back That Azz Up (AKA Back That Thang Up) (1999)

Juvenile’s “Back That Azz Up” is the second single from his groundbreaking LP, 400 Degreez, and also features a verse from the song’s producer, Mannie Fresh, and Juvenile’s fellow Hot Boy, Lil Wayne performs the outro. “Back That Azz Up” is the rare track that features the present and future of the genre on one song, with Juvie enjoying the success of 400 Degreez, while his protege, Lil Wayne, quietly takes notes in the corner.

15: Salt-N-Pepa – Let’s Talk About Sex (1991)

With “Let’s Talk About Sex,” Salt-N-Pepa offered an alternative to the boisterous and lustful raps from some of their male counterparts. Here was a group playfully staring down taboos (see: women talking about sex in ways both funny and forthright) and artfully explaining the harmful aspects of America’s mainstream aversion to sexual discussions. That they did all of this in the context of early 90s hip hop is no small thing, which is just one reason this song has made our list.

14: Gang Starr – Full Clip (1999)

Gang Starr’s “Full Clip” is an epic eulogy to the all-time MC, Big L. In the song, Gang Starr producer DJ Premier showcases his brilliant style, utilizing “Walk on By” by Cal Tjader in a thrillingly unexpected way. During verse one, Guru shows off his lyrical excellence, spitting, “Fresh out the gate again, time to raise the stakes again/Fatten my plate again, y’all cats know we always play to win.” One of the undeniable classic songs of 90s hip hop.

13: Mobb Deep – Shook Ones, Pt II (1995)

Mobb Deep’s “Shook Ones, Pt. II” is an absolute staple of 90s hip hop, transcendent of West Coast vs. East Coast beefs, of g-funk versus boom-bap. It’s just a perfect song, from Prodigy’s threatening bars about life in Queensbridge to Havoc’s absolutely brilliant sample, which slows and distorts a piano snippet from Herbie Hancock’s “Jessica.” “Shook Ones” puts all of the essential elements of hip hop music into one tidy, menacing package, the sort of song that will have you rapping about stabbing someone’s brain with their nose bone before even realizing what you said. It was a song that saved Mobb Deep from commercial failure in the 90s, and a song that changed the course of hip hop history.

12: GZA – Shadowboxin’ (1995)

Though “Shadowboxin’” ended up being one of the biggest songs from GZA’s seminal 90s hip hop classic Liquid Swords, it was originally released as a b-side to “4th Chamber.” The track features Wu-Tang member Method Man on the mic, and like all of Liquid Swords (except for one track), the beat was produced by RZA.

11: Lauryn Hill – Doo Wop (That Thing) (1998)

“Doo Wop (That Thing)” is the debut solo single from Lauryn Hill, a staggering introduction. The song, from The Miseducation of Lauryn Hill, was written and produced by Hill. It proved that women could both belong in the rap game and absolutely dominate it, whether in groups (like Hill in The Fugees) or solo. Though the song was officially released in October 1998, it began taking over New York a few months earlier, finding massive airplay support during the end of summer. It’s since been acknowledged as one of the best 90s hip hop songs ever made.

10: Warren G – Regulate (1994)

On Warren G and Nate Dogg’s “Regulate,” the duo used the staples of g-funk – bouncy synths, slapping snares, and undeniable melodies – to put listeners in the life of a West Coast gangsta. It’s a day in the life, with each artist spitting about fighting off robbers and laying busters down. It’s a menacing song disguised as a 90s hip hop summer anthem, the sort of hit that worked as both a club-ready hit and the song you’d put on to let the neighborhood know you’re for real.

09: A Tribe Called Quest – Scenario (1991)

“Scenario,” from A Tribe Called Quest’s seminal Low End Theory, is widely considered to be the greatest posse cut in hip hop history. Phife Dawg, Charlie Brown, Dinco D, and Q-Tip each handle verses, before Tip gives the stage to Busta Rhymes, who burst onto the scene thanks to his bars on the song as a 19 year old. The video mirrors this energy, with Spike Lee, De La Soul, Brand Nubian, Fab Five Freddy, and Redman making appearances.

08: Snoop Dogg – Gin N Juice (1994)

“Gin N Juice” is the definitive g-funk anthem. With a smooth chorus sung by David Ruffin Jr. (his father of Temptations fame), the 90s hip hop classic indulges in the hedonism of West Coast cool. The video for the song, meanwhile, finds Snoop Dogg throwing a raucous house party with his parents out of town, only to be scolded upon their return. It was fun while it lasted, though.

07: Outkast – Rosa Parks

Everything there is to love about OutKast can be found in “Rosa Parks.” Both Andre 3000 and Big Boi turn in show-stopping performances, the chorus is instantly anthemic, and the beat is unlike anything else in rap. With “Rosa Parks,” OutKast announced that 90s hip hop would run through the South, and they backed that claim up with song after song that helped innovate the genre. It’s simple enough: Rap wouldn’t be what it is if OutKast didn’t produce songs like “Rosa Parks.”

06: Dr. Dre – Nuthin’ But a G Thang (1992)

Dr. Dre’s 90s hip hop classic “Nuthin’ But A G Thang” was both one of 500 songs that shaped rock and roll, according to the Rock and Roll Hall Of Fame, and an example brought before the senate of music that bristled conservative congresspeople. Senator Sam Brownback, who sought hearings in the Senate Commerce Science and Transportation Committee, said he was “concerned that the music industry is marketing its most violent and misogynist music to teens.” Decades later, The Chronic and “Nuthin’ But a G Thang” has persevered, and Dre’s signature style is found all over hip hop.

05: Missy Elliott – The Rain (Supa Dupa Fly) (1997)

“The Rain (Supa Dupa Fly)” video would, in almost every instance, outshine the song it accompanies. But Missy Elliott managed to raise the stakes with her debut single. The Hype Williams directed video is surreal and maximal, with the signature shot encompassing Missy Elliott in a blow-up leather suit shot through a fisheye lens. It was written and composed by Don Bryant, Bernard “Bernie” Miller, Elliott, and producer Timbaland, who utilized a sample of Ann Peebles’ 1973 single “I Can’t Stand the Rain.”

04: Wu-Tang Clan – C.R.E.A.M. (1994)

Picking a definitive song from Wu-Tang’s 90s era is a fool’s errand, but it’s hard to argue against “C.R.E.A.M.,” which became such a monumental song that kids everywhere for generations knew that the acronym means Cash Rules Everything Around Me. Propelled by a pitch-perfect RZA beat, Raekwon and Inspectah Deck trade verses about life in New York, while Method Man handles the hook. Wu-Tang Clan was so deep that on their biggest song, they were able to leave Ghostface Killah, GZA, O.D.B., and more on the bench.

03: 2Pac – California Love (1995)

“California Love” is both a definitive West Coast anthem and one of the most important songs in hip hop’s history more generally. The song was released as 2Pac‘s comeback single after his release from prison in 1995 and was his first single on Death Row Records. Pac teamed up with Dr. Dre and rap godfather Roger Trautman of Zapp to create the masterpiece.

02: The Notorious B.I.G. – Hypnotize (1997)

Though “Hypnotize” remains one of the most joyful celebrations of hip hop’s ecstatic nature, the single will always be shrouded in mournful sorrow. The single dropped just one week before Biggie was killed, the sort of explosive, generational moment that was cut short due to the tragic circumstances that followed. “Hypnotize” was supposed to be one in a string of infinite hits, not a final farewell.

01: Nas – N.Y. State of Mind (1994)

It’s impossible to say what the best 90s hip hop song is. But most people wouldn’t argue too much about Nas’ “N.Y. State of Mind” being in the running. The song’s production was handled by DJ Premier who sampled two jazz songs: “Mind Rain” by Joe Chambers and “Flight Time” by Donald Byrd. Premier additionally scratched up vocal samples from Eric B. & Rakim’s “Mahogany” for the song’s hook. Nas’ rhyme patterns are dizzying and dazzling in equal measure, the sort of performance you want to take notes during, but can’t… because then you’d miss something unforgettable.

Looking to explore some of the best hip hop songs of the 90s? Check out our exclusive playlist on Spotify.

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