Three decades ago, hip-hop made a turn from the underground to commercial fanfare. The eclectic sensibilities of the 1980s created space for artists of all stripes, leading to the golden age of hip-hop, and releases that are now considered an integral part of the genre's canon. By the 1990s hip-hop was a chart-topping entity and enterprise, where artists were popularized through streetwear campaigns and brand deals.

In this decade, rappers were multifaceted in their flow and lyrics — whether rugged and hard-spitting, or poetic and fervently expressive. Artists like psychedelic hip-hop group De La Soul, salacious femcee Lil' Kim and Atlanta heavy-hitters Outkast expanded rap’s palette. Beats ranged from synthetic to weighty 808 drum patterns, all which redefined the genre’s 20-year presence. 

Hip-hop chronicled truth and fantasy, providing listeners both deeply resonant and vividly divergent soundtrack whose influence continues to be felt. Decades later, records released in the 1990s are legend, and many of them appeared on the 65th GRAMMY Awards stage in a massive tribute to hip-hop.Here are 10 signature albums that bridged the golden age and the digital era of hip-hop.

De La Soul - De La Soul Is Dead (1991)

By 1991, conscious hip-hop pioneers De La Soul were over the "D.A.I.S.Y. Age" introduced on their seminal debut album 3 Feet High and Rising. The Long Island trio, composed of Posdnuos, Maseo and the late Trugoy the Dove jazzed up their sound on sophomore effort De La Soul Is Dead, marking a radical transition from hip-hop "hippies" to earnest rhymesayers. 

Posdnous and Trugoy melded simple production (courtesy of Prince Paul) with complex bars on "Pease Porridge," and also explored the traumas of sexual molestation through metaphor on "Millie Pulled a Pistol on Santa." Although De La Soul Is Dead received mixed reviews, the LP was one of the first albums to earn a five-mic rating in hip-hop publication The Source. "Still progressing and proud of it, De La has successfully escaped being trapped in the sophomore jinx with grooves that are harder than a brick wall," the throwback review reads.

With De La Soul Is Dead, the group, whose back catalog just arrived on digital music services in March, evaded the dreaded sophomore slump and cemented their place in hip-hop history.

Snoop Dogg- Doggystyle (1993)

After Calvin Broadus — then performing under the moniker Snoop Doggy Dogg —  released his breakthrough album Doggystyle, West Coast rap was never the same. Playing on inspirations from classic Blaxploitation films and early funk pioneers, Snoop kept his posture smooth while rhyming over beats from Dr. Dre (who also discovered the Long Beach native), and welcomed fellow then-newcomers like The Lady of Rage, Tha Dogg Pound, Warren G and RBX as features.

Giving listeners "just a small introduction to the G-Funk era," Snoop helped usher  in a soul-laden gangsta rap  sound that stood in distinct contrast  to the East Coast’s grittiness and jazz influence. The iconic "Gin and Juice" and "Who Am I (What’s My Name?)" have long been summertime cookout staples, while the eerie "Murder Was the Case" preceded Snoop being acquitted of murder just three years later. Now a 16-time GRAMMY nominee, Doggystyle marked Snoop’s debut as a hip-hop elite.

A Tribe Called Quest - Midnight Marauders (1993)

Three albums into their career, A Tribe Called Quest didn’t let up on Midnight Marauders. The Queens-bred group, which included Q-Tip, the late Phife Dawg, Ali Shaheed Muhammad (and occasional member Jarobi White) flaunted their lyricism and expansive musical knowledge  on the 1993 release, which was navigated by a robotic "tour guide."

Q-Tip and Phife’s wordplay is nimble throughout the album, but truly spotlighted on the Trugoy the Dove-assisted "Award Tour," the amorous "Electric Relaxation" and "The Chase, Pt. II." "8 Million Stories" and "Midnight" were solo moments for Phife Dawg and Q-Tip, respectively, each who had brushed up their penmanship since ATCQ’s 1991 reinvention on The Low End Theory. Both atmospheric and imaginative, Midnight Marauders showcased ATCQ’s range as a progressive hip-hop act.

Digable Planets - Blowout Comb (1994)

Jazz rap trio Digable Planets maintained their cool just one year after winning a GRAMMY Award for Best Rap Performance By A Duo Or Group. In 1994, Ishmael "Butter Fly" Butler, Mariana "Ladybug Mecca" Vieira and Craig "Doodlebug" Irving followed with Blowout Comb, their second and final studio album. With a minimalist approach, Digable Planets trekked through urban and Afrocentric themes soundtracked by live instrumentation and spoken word.

Emotionally stirring and thematic, "Black Ego" saw Digable Planets tackling economic injustices and Black nationalism with nods to Blaxploitation films Cleopatra Jones and Superfly. The group asserted their refusal to go commercial on laidback earworm "Jettin." Seventies slang and references to New York City boroughs floated throughout Blowout Comb, and although singles "9th Wonder (Blackitolism)" and "Dial 7 (Axioms of Creamy Spies)" didn’t chart, the album reintroduced Digable Planets in their most authentic form and reached No. 32 on the Billboard 200.

2Pac - Me Against the World (1995)

With an awareness unrivaled by his  contemporaries, Tupac Shakur's penultimate album, Me Against the World, exploredhis complexities. By March 1995, the rapper had served one month in prison on sexual abuse charges, and had used his previous year of freedom to record arguably the most poignant LP of his lifetime.

On the titular track, Shakur examined impoverished Black communities and morbid thoughts of mortality. A sample of Stevie Wonder’s "That Girl" textures "So Many Tears," where 2Pac vocalizes music industry woes, his depression and even predicts an early death. "Dear Mama," (which inspired the FX docuseries of the same name), was 2Pac’s dedication to mother and former Black Panther Party member Afeni Shakur; it became the third song by a rap act to be placed in the Library of Congress.

The latter song and Me Against the World would both earn Shakur his first GRAMMY nominations. While he didn't win, both are masterpieces that signaled the rapper’s coming-of-age.

Jay-Z - Reasonable Doubt (1996)

Jay-Z gave a solid lyrical offering on his 1996 debut. A landmark album on the now-defunct Roc-A-Fella Records, the 14-track Reasonable Doubt brought mafioso and luxury rap into the ring, as Jay-Z gave semi-autobiographical tales of street life.

On "Feelin’ It," the Brooklyn rapper boasts his riches and opulent lifestyle, while the Issac Hayes-sampling "Can I Live" explores the close calls that the hustle brings. Hov’s stream-of-conscious flow highlighted production from the likes of Ski Beatz, DJ Premier and Clark Kent. 

Reasonable Doubt predicted Jay-Z’s thriving future without a doubt, as he’s since taken hip-hop’s throne as a coveted 24-time GRAMMY-winning artist (in addition to 88 nominations).

Lil’ Kim - Hard Core (1996)

Brooklynite Lil’ Kim carved out space for risque rap on her 1996 solo breakout Hard Core. Less than six months after the murder of her mentor the Notorious B.I.G., the former Junior M.A.F.I.A. member achieved solo commercial success for her provocative lyricism and appearance. Whereas many of her contemporaries adopted a more androgynous style, Lil’ Kim played up her sex appeal onstage and on record.  

The raunchy "Big Momma Thang," which samples 1978 Sylvester deep cut "Was It Something That I Said," shows Lil Kim’s allyship with queer listeners. Lil’ Kim asserted her hood dominance on "No Time," while flaunting her affection for being classily "draped in diamonds and pearls." Although Hard Core was Moderately received, Lil’ Kim’s rap successors —Doja Cat, Megan Thee Stallion and Cardi B — would later speak highly of the Queen Bee’s NSFW magnetism. Nearly 30 years later, contemporary women in hip-hop continue to strive for Lil’ Kim’s unapologetic influence.

Missy Elliott - Supa Dupa Fly (1997)

Hip-hop hadn’t witnessed fly until Missy "Misdemeanor" Elliott stepped onto the scene. The Virginia-born rapper and singer/songwriter had once been a part of R&B group Sista before partnering with producer Timbaland. The two both wrote and produced almost the entirety of Aaliyah’s 1996 album One In A Million. By the late ‘90s, Elliott’s pen was in demand, giving her the confidence to share her unconventional sound and look as a solo act.

Her 1997 debut, Supa Dupa Fly, redefined what it meant to be a woman in rap. Over Timbaland's bass-thumping production, Elliott went full-on futuristic. She humorously teased her sexuality on the audacious "Sock It 2 Me," while the bouncy "The Rain (Supa Dupa Fly)" sampled Memphis soul vocalist Ann Peebles with peculiar lyrics like "my finger waves these days, they fall like Humpty." 

Two decades before being inducted into the Rock & Roll Hall of Fame and receiving the Black Music Collective's Recording Academy Honors award, Elliott took the rap world by storm. Ahead of its time yet heralded, Supa Dupa Fly and Elliott’s one of a kind style showed the artist’s peers and successors how to be creative anomalies.

Outkast - Aquemini (1998)

The South had something to say on Outkast’s third album Aquemini. The duo of André 3000 and Big Boi asserted their southern charm and immaculate rhyme schemes on the 16-track album that catapulted them to stardom. As the two rappers perfected their individualism, Aquemini also showed 3000 and Big Boi seamlessly meshing their styles together.

More spacey than their sophomore album ATLiens, Outkast doubled up on their down home twang on the funky (but controversial) "Rosa Parks." The two questioned reality from dystopian technology on the surreal "Synthesizer" with P-Funk legend George Clinton. Listeners can visualize a juke joint scene on the reggae-tinged "SpottieOttieDopaliscious," where 3000 and Big Boi intertwine tales of a violent nightclub encounter and a cursed romance. 

Aquemini ushered a turn in Dirty South hip-hop, where the region gained national respect for its storytelling, realism and unique flow.

Dr. Dre - 2001 (1999)

Super producer and rapper Dr. Dre brought out the all-stars on his 1999 sophomore solo album 2001. The LP reunited the now seven-time GRAMMY-winner with his prodigies Snoop Dogg, Eminem, Xzibit, Nate Dogg and Kurupt, while ushering in a new age of West Coast rap. Seven years after his groundbreaking debut album The Chronic, the former N.W.A. member was "Still D.R.E."

On the aforementioned track, written entirely by Jay-Z, Dr. Dre flexed his near 15-year impact in hip-hop. "The Watcher" detailed the Compton native reaching music industry plateaus despite paranoia of "a new era of gangstas." Strip club anthem "The Next Episode" harkened back to Dre and Snoop’s "Nuthin’ But A 'G' Thang," while "Let’s Get High" captured a raunchy house party. On 2001, now certified 6x platinum, Dr. Dre was at his most carefree while setting the bar high for a new generation of hip-hop.

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Coolio was living in the "Gangsta's Paradise" of his own creation when the 1996 GRAMMY Awards rolled around. The year before, the ode to hip-hop culture had not only become a global No. 1 hit for the rapper, but also the best-selling song of 1995 in the U.S. And that February night in Los Angeles' Shrine Auditorium, the track won Coolio his first GRAMMY, for Best Rap Solo Performance.

Receiving the trophy from Salt-N-Pepa and Mary J. Blige (clad in head-to-toe leopard print), the rapper emerged from backstage with his overjoyed entourage in tow, and started out his acceptance speech by claiming his GRAMMY "for the whole hip-hop nation."

"West Coast, East Coast, worldwide — united we stand, divided we fall. Recognize," he continued before going on to thank God, his then-fiancée Josefa Salinas and his kids, as well as Stevie Wonder, Quincy Jones, his collaborator L.V., Michelle Pfeiffer (who starred in the song's music video) and others.

Coolio then ended his remarks on a serious note, acknowledging, "We've had a lil' problem lately in high schools and I only got one ting to say to all my Black and Latino brothers out there fightin': Ain't no gangsters living in paradise." 

During the telecast, Coolio also took to the stage to perform "Gangsta's Paradise," which had earned a second nomination for Record of the Year. (That major award ultimately went to Seal's "Kiss From a Rose," along with Song of the Year.)

Sadly, the gangsta rap pioneer died in September 2022 at age 59 after suffering an accidental overdose laced with fentanyl. Press play on the video above to revisit Coolio's GRAMMYs win and check GRAMMY.com for more new episodes of GRAMMY Rewind.

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Lil Wayne had already hit a new high point when he released "A Milli" in the winter of 2008. "Lollipop," the single that directly preceded "A Milli," had scored the rap legend his first hat trick by hitting No. 1 on the Billboard Hot 100, Hot R&B/Hip-Hop Songs and Hot Rap Songs charts.

With "A Milli," the rapper born Dwayne Carter Jr. continued his chart-topping success by capturing yet another No. 1 on the latter two tallies and winning him the GRAMMY for Best Rap Solo Performance at the 2009 ceremony. The modern classic also heralded Wayne's blockbuster album Tha Carter III, which became the final album of the decade to sell more than a million copies in its opening week.

In this new episode of Hip-Hop Re:Defined, rising rap star Armani White tackles Wayne's noughties smash, with the Philadelphia-born newcomer building his flow over the same stuttering sample of A Tribe Called Quest's "I Left My Wallet in El Segundo" as the original.

"A millionaire/ I'm a West Philly millionaire, tougher than Nigerian hair/ My criteria compared to your career just isn't fair," White raps, personalizing the lyrics with a shout-out to his hometown while still echoing Weezy's trademark cadence.

In May, White dropped his major-label debut, Road to Casablanco, with the EP led by his viral single "BILLIE EILISH" and its official remix featuring Ludacris, Busta Rhymes and N.O.R.E.

Press play on the video above to watch White rip through "A Milli," and check back to GRAMMY.com for more new episodes of Hip-Hop Re:Defined.

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They're cool like that. Back in 1994, Digable Planets took home the trophy for Best Rap Performance By A Duo Or Group for their single "Rebirth of Slick (Cool Like That)" at the 36th Annual GRAMMY Awards.

Accepting the award from presenters SWV and Salt-N-Pepa, the jazz-rap connoisseurs dedicated their win to "hip-hop music [and] Black culture in general" before sharing an entreaty for the less fortunate outside the gilded glamour of Radio City Music Hall.

"We'd like for everybody to think about the people right outside this door that's homeless as you sittin' in these $900 seats and $300 seats — they out there not eatin' at all," Ishmael "Butterfly" Butler added. "Also, we'd like to say to the universal Black family that one day we gon' recognize our true enemy and we're gonna stop attacking each other. And maybe then we'll get some changes goin' on."

As their debut single, "Rebirth of Slick" served as Digable Planets' seminal hit. That night, it beat out other four other rap classics: Cypress Hill's "Insane in the Brain," Naughty by Nature's "Hip Hop Hooray," Dr. Dre and Snoop Dogg's "Nuthin' But a G Thang" and Arrested Development's "Revolution."

The trio — Butler, Mariana "Ladybug Mecca" Vieira and Craig "Doodlebug" Irving — were also nominated for Best New Artist, an award that ultimately went to Toni Braxton.

Press play on the video above to revisit Digable Planets' big GRAMMYs win and check GRAMMY.com for more new episodes of GRAMMY Rewind.

10 Reasons Why Outkast’s ‘Speakerboxxx/The Love Below’ Is One Of The All-Time Great Double Albums

"We done split it down the middle so you can see both the visions," raps Big Boi on "Tomb of the Boom," one of the highlights from Outkast's 2003 magnum opus. And he wasn't kidding.

Essentially two solo albums for the price of one, Speakerboxxx/The Love Below saw Atlanta's premier hip-hop duo take the creative reins for one disc each, resulting in a whopping 135 minutes and 40 tracks of genre-hopping genius.

Favorably compared with classic double albums such as Prince's Sign O' The Times, Pink Floyd's The Wall and the Beatles' The White Album, the follow-up to 2000's Stankonia enjoyed similarly super-sized success, too. It topped the Billboard 200 for seven weeks on its way to worldwide sales of 11.4 million, spawned two No. 1 hits and picked up six nominations at the 2004 GRAMMY Awards — which resulted in three wins, including the coveted Album Of The Year.

And a full 20 years on from its Sept. 23, 2003 release, Outkast's fifth studio effort still stands up as a fearless, funkadelic and forward-thinking body of work. Below, take a look at 10 reasons why Speakerboxxx/The Love Below still has the power to get us all shaking it like a Polaroid picture.

It Helped Outkast Join An Exclusive Chart Club

Only 14 acts in the history of the Billboard Hot 100 have knocked themselves off the top spot. And Outkast joined that illustrious group — which also now includes the likes of Drake and Taylor Swift — in 2004 thanks to two of the era's most addictive hits.

The Little Richard-goes-power pop of "Hey Ya!" was the first to reach the summit, spending nine weeks there between December 2003 and the following February. And then it was finally dislodged by the brassy Southern hip-hop of Sleepy Brown collaboration "The Way You Move," which enjoyed just seven days in pole position before Twista's "Slow Jamz" put an end to the Outkast stranglehold.

It Doubled Outkast's GRAMMY Count

By 2004, Outkast were no stranger to the GRAMMY Awards. They'd picked up Best Rap Performance by a Duo or Group for "Ms. Jackson" and Best Rap Album for Stankonia in 2002, and then emerged victorious in the former category again a year later for "The Whole World." But it was the 2004 ceremony where they truly reigned supreme.

The duo stole the show with two memorable performances. First, Big Boi performed "The Way You Move" in a star-studded Funk Music Tribute, which also included legends George Clinton, Earth Wind and Fire and Robert Randolph. Later, André 3000 closed out the show with a celebratory rendition of Best Urban/Alternative Performance winner "Hey Ya!"

The "Hey Ya!" performance was a fitting end to the night indeed, as the pair took home the final — and most prestigious — award: Speakerboxxx/The Love Below was crowned Album of the Year. (It also won Best Rap Album earlier that evening.)

It Spawned Several Classic Videos

Outkast had always been a visual hip-hop outfit, but their videography undeniably peaked with the Speakerboxxx/The Love Below campaign. "Hey Ya!" deservedly picked up four MTV Video Music Awards thanks to its inspired tribute to the Beatles' debut on "The Ed Sullivan Show" — and André 3000's portrayal of all eight of the fabulously named musicians in the video, including guitarist Johnny Vulture and drummer Dookie Blossom Gain III.

Also directed by Bryan Barber, the "The Way You Move" video saw Big Boi showcase his lyrical flow in everything from a rim shop and old-school music hall to dojo and safari retreat. "Roses," meanwhile, finally allowed both members to share the screen as warring members of rival high school crews in a tongue-in-cheek homage to West Side Story.

It Boasts An Impressively Diverse Guest List

Big Boi roped in several usual suspects on Speakerboxxx, including Big Gipp on "Tomb of the Boom," Killer Mike on "Bust" and Cee-Lo Green on "Reset," while also securing the talents of heavy hitters like Jay-Z, Ludacris and Lil Jon and the East Side Boyz. While an undeniably impressive guest list, André 3000's choice of collaborators was even more intriguing.

Shortly before teaming up with the rapper on her own track "Millionaire," Kelis lent her signature husky tones to the appropriately creepy funk of "Dracula's Wedding." Hot on the heels of Come Away with Me, Norah Jones provided the necessary sultriness on the acoustic "Take Off Your Cool." And perhaps most unexpected of all, Hollywood actress Rosario Dawson proved her diva credentials on the metallic funk of "She Lives In My Lap." The Love Below's roll call was yet another sign that Outkast weren't interested in playing by hip-hop's rules.

It Samples Wisely

Considering Speakerboxxx/The Love Below consists of 40 different tracks and clocks in at nearly 135 minutes, it's surprising that Big Boi and André 3000 only relied on a handful of samples. And like their choice of collaborators, they're far from obvious, either.

Who knew that The Sound of Music showtune "My Favorite Things" would work as a drum and bass instrumental? Or that Timmy Thomas' one-hit wonder "Why Can't We Live Together" and the sensual New Jack Swing of Aaliyah's "Age Ain't Nothing But a Number" would fit perfectly as on "Pink and Blue"?

Elsewhere, the propulsive electronic hip-hop of opener "Ghetto Musick" borrows from Patti LaBelle's '80s soul jam "Love, Need and Want You," while "She Lives in My Lap" lifts from both Geto Boys' "Mind Playing Tricks on Me" and Volume 10's "Pistolgrip-Pump."

It Paved The Way For Genre-Hopping

While genre boundaries have been well and truly broken down in today's streaming era, back in 2003, most major artists stayed in their lane — but not Outkast.

The Love Below certainly has little regard for pigeonholing, veering from big band crooning ("Love Hater") to celestial neo soul ("Prototype") to twitchy electro ("Vibrate") with both confidence and panache. The more-focused Speakerboxxx also keeps listeners on their toes, whether it's with the squelchy P-funk of "Last Call," punchy rap-rock of "Bust" or the mariachi-tinged hip-hop of "The Rooster."

Despite its mammoth running time, the album impressively never repeats itself, providing more flashes of invention than most of the duo's peers manage in an entire career.

Even The Interludes Are Inspired

Of Speakerboxxx/The Love Below's 40 tracks, 11 could be classed as interludes — a number that would normally draw groans, especially considering how much they're often the bane of a hip-hop album. But while the blink-and-you'll-miss-it contribution from comedian Henry Welch ("D-Boi") and the brief helium-voiced reprise of "Bowtie" are rather pointless, the majority of the breathers do add something to the record.

"Interlude" is a hypnotic spoken word piece which offers a crash course in Outkast history ("Believe in the dirty Southernplayalisticadillac-funky-ATLiens/ Together, makes Aquemini"). "The Love Below (Intro)" is a sumptuous orchestral number in which André 3000 throws things back to the Rat Pack. And "God (Interlude)" finds the latter living up to his horndog reputation in a cheeky prayer recited over some sun-dappled guitars.

It's About Both Love And War

As titles such as "Happy Valentine's Day," "Behold a Lady" and, of course, The Love Below would suggest, André 3000's half of the album is largely focused on the affairs of the heart — no doubt informed by his break up from Erykah Badu and subsequent quest to find 'the one.'

But to counterbalance all the love talk, Speakerboxxx is a more socially-conscious record in which Big Boi tackles themes of spirituality, philosophy and politics, none more so than on "War," a fervent protest song which no doubt left George W. Bush's ears burning ("Basically America, you got f—ed/ The media shucked and jived, now we stuck, damn.")

The Pair Deliver Career-Best Vocals

Free from having to battle for space on the same track — they only appear together on "Ghetto Musick," "Knowing" and "Roses" — Big Boi and André 3000 have arguably never sounded better than on their respective discs.

The former is in particularly ebullient form on his alter ego Sir Lucious Left Foot's origin story "Unhappy," and also spars well with hip-hop giants Jay-Z and Ludacris on "Flip Flop Rock" and "Tomb of the Boom," respectively. His regular partner in crime, meanwhile, appears to relish channeling his inner Prince on the falsetto-led "Spread" and final single "Prototype."

It Helped Revive The Hip-Hop Double Album

The mid-'90s had been a boom period for the hip-hop double album, with Tupac Shakur's All Eyez on Me, Notorious B.I.G's Life After Death and Wu Tang Clan's Wu Tang Forever regarded as the holy trinity. But the concept had fallen out of favor until Outkast's Speakerboxxx/The Love Below shifted nearly six million copies in the United States alone.

Following its triumph, Nas (2004's Street's Disciple), UGK Underground Kingz (2007's Outkast-featuring Underground Kingz) and Tech N9ne (2008's Killer) all got in on the act. More recently, Vince Staples (2015's Summertime '06), Drake (2018's Scorpion) and Kendrick Lamar (2022's Mr. Morale & The Big Steppers) have also tried to bottle lightning twice. But while they all have their high points, none quite match up to the sheer brilliance of Outkast's crowning glory.

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