The 10 Best Rappers of the 1990s

10.Redman

Solo Albums: Whut? Thee Album (1992), Dare Iz a Darkside (1994), Muddy Waters (1996), Doc's da Name 2000 (1998)

Group Albums: El Nino (1998) with Def Squad, Blackout! (1999) with Method Man

Biggest Hits: "Funkorama" (1995), "How High" with Method Man (1995), "Whateva Man" featuring Erick Sermon (1996)

No rapper on this list was as consistent throughout the decade as Redman. Think about it: did any artist on this list so effortlessly transition from East Coast hip-hop's subterranean early '90s to its broadly comedic, commercial late '90s peak? His style, which could vascillate from seriously lyrical lyricism to ignorant humor on the drop of a dime, was so effective because of his flow, that rubbery delivery that seemed to snap with tension and joie de vivre. What Ludacris became for the new millennium, Redman was for the 1990s: The decade's premier party rapper, the ultimate realization of the potential of "Rapper's Delight" for the aesthetic revolutions of the genre's second decade.

If a single word could describe his output, it was fun. There was no sense of dumbing it down, because that was the point. Complete creativity meant absurd flights of fancy ("Soopaman Luva") to stoner buddy comedy everyman ("How High" and the entirety of Blackout!). Appropriately enough, Redman debuted on wax at the decade's dawn. In 1990, he opened EPMD's Business as Usual with his "Brothers On My Jock" verse verse over a "Nautilus" loop. Relative to his later work, he sounded reserved, tentative even. This wouldn't last. By the time of his debut, Whut? Thee Album two years later, Redman was an explosive, charismatic presence.

While Redman's work had the macho swagger and aggression common to the era, it was animated by a more exuberant, manic vibe. These competing ideas of persona gave his work an unpredictable energy and consistency. Set between being a threat and a clown, balancing the broad-strokes punchlines and an eccentric, blunted creativity, the craft of his words and his clear interest in being an entertainer, Redman's career was a study in the unexpected.

His recorded peak is likely 1996's Muddy Waters, in which all these latent pressures seemed to come together. He was an artist at his strongest in transition. But a major advantage of his approach—the Slick Rick-like storytelling, a dexterous rap technique, and an ability to seem continually inspired—was that it was consistent. Redman spent the bulk of the decade recording, and from his time as an underground hero to his days on the path to deoderant pitchman, he remained thoroughly himself. All that shifted was the camera lens. —David Drake

9.Lauryn Hill

Solo Albums: The Miseducation of Lauryn Hill (1998)

Group Albums: Blunted on Reality (1994) with Fugees, The Score (1996) with Fugees

Biggest Hits: "Fu-Gee-La" with Fugees (1996), "Killing Me Softly" with Fugees (1996), "No Woman, No Cry" with Fugees (1996), "Doo Wop (That Thing)" (1998), "Ex-Factor" (1998), "Everything Is Everything" (1998)

During her prime, Lauryn Hill was truly iconic. Her ability to both sing beautifully and rap with a convincing rasp both precedes and outshines most of what we hear today, when sing-rapping—something that seemed so rare and revolutionary back then—has become the standard. She and The Fugees made a lane for themselves by funneling a number of genre influences into a distinctive sound and aesthetic.

At the heart of this aesthetic was Lauryn’s voice. The Fugee earworms that still live in our brains are all probably Lauryn Hill sung choruses—meanwhile she was “defecating on your microphone” more convincingly than most MCs an era saturated with rap skill. The Score is a classic because of her performance on it. One could tell that a solo presence was ready to burst its way onto its own record.

But not before lending an ethereal quality to some other people’s songs. Take Nas’ "If I Ruled The World." She’s able to seamlessly interweave a hum throughout each verse, leading eventually to a chorus that both supported and lived beyond the lyrical substance of the song.

Then, of course, came The Miseducation of Lauryn Hill. Everything that shined about her prior performances came out, unfettered, on this album. It was what everyone wanted so badly from her. Kanye West referred to the year it dropped as the time “Lauryn Hill, when she won all those Grammys, she just couldn’t lose.” As in, it was unquestionable, and the reception was almost unanimous. Rarely does something like that actually happen—especially in rap, also known as the genre most populated by haters.

Miseducation had crossover pop appeal (“Doo Wop”), pleased rap purists, and still represented the neo-soul, blended reggae and hip hop aesthetic that she and her peers popularized. Naturally, the album sold. It has sold over 20 million records to date, and without being pretentious or reaching, overtly, toward mass appeal. She brought pop around to accept the sound of the album rather than forcing her sound to cross over into pop territory. —Alexander Gleckman

8.Snoop Dogg

Solo Albums: Doggystyle (1993), Tha Doggfather (1996), Da Game Is To Be Sold, Not To Be Told (1998), No Limit Top Dogg (1999)

Group Albums: N/A

Biggest Hits: "Nuthin' but a 'G' Thang" with Dr. Dre (1992), "Fuck wit Dre Day (And Everybody's Celebratin')" with Dr. Dre (1993), "What's My Name?" (1993), "Gin and Juice" (1993), "Still A G Thang" (1998)

When he started to appear on MTV, it was a revelation, something like seeing a ghost—or something even more than, something that would made you blink and rub your eyes and think to yourself, "Did I really just see that?" Because this kid with the funny name that rolled off the tongue—Snoop Doggy Dogg, as he was known then—with the slender face that could flip go from the most gangsta mean-mug to the most charming, harmlessly mischievous slick-kid smirk, and back, so seemingly effortlessly?

He was notoriously camera-shy. Which gave him the rare quality so many of the stars of today lack: Mystique, a real sense of it. But then, you heard him rap, and everything changed. Maybe it was that lackadaisical, Slick Rick-esque croon, a silky smooth timbre to his voice, a natural melodicism that blurred the line between talking and singing like nothing anything you'd heard before, a voice that ran counter to everything you knew about the typically husky tenor of West Coast gangsta rap or the I'mma-get-mine brusqueness of East Coast boom-bap. Maybe it was the laid back, fuck-outta-here attitude towards the world that felt far more detached, far less invested in that daily gang-life thug shit. Snoop was just far coolerthan anyone who'd come before him, and yet, he could flash menacing when the situation demanded.

Whatever the case, when you heard the opening notes of Dr. Dre's gangsta rap masterpiece, The Chronic, you knew, definitively, that Snoop was something different. The way he absolutely decimated Eazy-E and MC Ren, dominating the track in full monologue, switching voices, going from cruel to hysterical and threatening and back again: It was, for that time, otherworldly.

It was the new sound of gangsta rap, where to be young and clever wasn't great enough when there was Snoop, who was young, clever, and in possession of what was clearly an intellect as razor-sharp and creative as his wit. Throughout The Chronic, Snoop acts less as a Robin to Dre's Batman, and more a Kobe to his Shaq, the Tom Hagen to Dre's Michael Corleone. Where Dre's musical might blocked out the lane, it was Snoop who could drive the rhymes home (which is to say nothing of the obvious, that he was the driving lyrical force behind The Chronic as well). From "Fuck wit Dre Day" to "Let Me Ride" to "Nothin But a G Thang" to "Deeez Nuuuts" to "Bitches Ain't Shit," Snoop was instrumental in the album's greatness and so much of the reason it remains so crucial today.

And thus the stage was set for his solo debut, 1993's Doggystyle. Forget the distinctive, cartoon-drawn cover, or the awesome videos (wherein, forced to take the spotlight, Snoop finally started to own his charisma in front of the camera.) "Gin and Juice," an instantly ubiquitous party starer. "Lodi Dodi," one of the greatest callbacks to another great rap song that has ever been rapped. (And a refreshingly explicit acknowledgment of the debt he so obviously owed to Slick Rick as a lyricist). If the world didn't know who he was before, everyone, even your parents, knew about the rapper with the alliterative name after "What's My Name."

And then there was "Murder Was The Case," a stunning, ambitious story-rap about a deal with the devil, and consequent death. The song would grow in legend when—in what is indisputably one of the most memorable moments in MTV's history—Snoop performed it at the 1994 VMAs, while there was a warrant out for his arrest, proclaiming at the end of the song "I'm innocent. I'm in-no-cent," and, indeed, be arrested as he left the show. Rarely had pop culture seen a star of Snoop's magnitude, at the time of their rise, on trial for murder. But that was Snoop, nothing short of the real deal, a shot across the social consciousness about the legitimacy of the words in gangsta rap (and an even louder one when he was acquitted of the crime).

The second half of the '90s wasn't so great for Snoop. As the atmosphere around Death Row Records got darker and uglier, Snoop—who'd already had his fair share of trouble—could only get so involved in what was happening. (And better for him.) In 1998, he finally officially split from the label, and, with the help of Master P, made his way to the New Orleans-based No Limit Records. And about that transition: Not many decidedly West Coast Rappers will ever make as oddly seamless a transition to a Southern Rap aesthetic as Snoop did. (His two '90s No Limit-era albums peaked at #1 and #2 on the charts, respectively).

The end of the '90s had Snoop and Dre reuniting at last. With the question standing: a referendum on their legacies: Were they just a product of the early '90s, of the precipitous rise of crossover gangsta rap? And now that crossover rap had dominated the sound of the day, could these two still take charge of the charts and prove that their talent transcended whatever was going on in music at any given moment?

While they'd worked together a bit on Snoop's No Limit Top Dogg (with Dre guesting on a few tracks and taking production duties on album standout "Bitch Please"), it took exactly one song from their fully reunited efforts, the first song we'd hear from Dre's return to form, 2001, to know the answer.

In "Still D.R.E." the truth of the matter was made clear, the same that it ever was: Snoop would far outlast his multiple brushes with figurative and literal death. Best told via a platform provided by Dr. Dre, yes, he really was that rapper, his talent and contributions to the form, and to the decade's cultural legacy as a whole, remained indisputably, unquestionably intact. It's the cadence, it's the melodic delivery, it's the quick wit and the humor and the hilarity and the sense of menacing. It's the buttery staccato, the juke-and-run flow. It's the braids. It's the face. It's the ideas and the story telling. It's everything. It really was just a Doggy Dogg world, and we're just living in it. —Foster Kamer

7.Ice Cube

Solo Albums: AmeriKKKa's Most Wanted (1990), Kill at Will EP (1990), Death Certificate (1991), The Predator (1992), Lethal Injection (1993), War & Peace Vol. 1 (The War Disc) (1998)

Group Albums: Bow Down (1996) with Westside Connection

Biggest Hits: "True to the Game" (1991), "It Was a Good Day" (1992), "Check Yo Self" featuring Das EFX (1992), "Bop Gun (One Nation)" featuring George Clinton (1993), "Bow Down" (1996)

In May 1990, when Ice Cube released AmeriKKKa’s Most Wanted, he had separated himself from the group that he'd risen to fame with, and begun to push the boundaries beyond the relentlessly expressive and controversial standard set by N.W.A. Unhindered by some aspects of his former group’s aesthetic, Cube’s lyrics became more pointed and sociopolitical, but not at all less indignant, violent, or energetic. The attitude was just as present, but his individual voice had become more focused.

Just a year later, and after a successful Cube released Death Certificate, an album with a finger on the pulse of rising tensions in Los Angeles and a dagger (e.g. “Eazy dick is starting to smell like MC Ren’s shit” he said on "No Vaseline") to the necks of his rivals. It’s hard to compete rhyme for rhyme with the guy who wrote all of your rhymes. But beyond containing one of the greatest diss songs of all time, this album was more historical landmark than just one person’s story. Like much great art, it serves a second purpose as a time capsule for the world that surrounded it. It captured early '90s Los Angeles factually but also viscerally, and makes for a much better history explanation than any textbook could.

Nineteen ninety-two was Cube’s year. Fueled by an expanding thematic scope (check the spread from "Check Yo Self" to "It Was a Good Day") The Predator album became his most commercially successful work. Cube had cemented his status as one of rap’s greats—and the decade had just begun. For the rest of the '90s, Cube released two more solo albums, reunited with Dr. Dre, and brought forth Da Lench Mob and Westside Connection. Oh, and he was in some movies too. —Alexander Gleckman

6.André 3000

Solo Albums: N/A

Group Albums: Southernplayalisticadillacmuzik (1994) with Outkast, ATLiens (1996) with Outkast, Aquemini (1998) with Outkast

Biggest Hits: "Player's Ball" with Outkast (1993), "Elevators (Me & You)" with Outkast (1996), "ATLiens" with Outkast (1996), "Jazzy Belle" with Outkast (1996)

When André Benjamin was still but a teenager, one-half of Atlanta rap group OutKast, on the group's debut, Southernplayalisticadillacmuzik, signs of the eclecticism André would later develop and refine (not just as part of OutKast's aesthetic, but as part of the one he'd later ride to worldwide solo success) were already there. Where Big Boi played the gruff, southern thug, the thematic muscle of the duo, André played the part of the kid nostalgic for places he'd never been and eras he'd never lived through.

It's André's distinctive tone—a Southern lilt with a hint of softness—paired with his interest in lyrical gymnastics that truly helped the group stand apart on that first album. Whereas Big Boi exemplified the gruff, candy-paint pimp aesthetic of that moment in Southern rap, it was clear that André's head was lost in the clouds, in the best way possible. He was about more than the singles, he was about more than what rap fame had to offer, and this was evident by the way he rhymed, a rap nerd's flow if there ever was one, only enhanced by that rare Southern inflection.

OutKast's second album, ATLiens was no different. In 1996, as East Coast/West Coast gangsta rap dominated every major conversation about the genre, André wasn't rapping about violence, or his rivals, but being approached at the mall and being hit up for money, and really, not having all that much. ("True I got more fans than the average man/But not enough loot to last me, to the end of the week/I live by the beat/Like you live check to check, and if you don't move yo feet/Then I don't eat/So we like neck-to-neck.") André's raps were dipped in existential philosophy, which goes without mentioning the extraterrestrial themes they used as color.

1998's Aquemini was, in fact, different. Whereas the first two albums had shown that André's songwriting creativity and dynamic lyrical skills simply excelled beyond that of his contemporaries, the five-mic album, the finest piece of Southern rap to come out that decade, hell, the finest piece of Southern rap to come out ever, took him from artist making rap to artist making genre-transcendent rap. Pliable and distinct, his flow referenced more poetry and jazz than it did other rappers. He's become a connoisseur's lyricist, one whose understanding of song craft never fell under the shadow of his innate, stunning talent.

No wonder, then, that the albums that followed, as the millennium turned, would become so patently psychedelic again, in form and in what they held lyrically. It's not so much that the '90s took André to astral planes, but that André had made the plane we're on seem like such a far away place. And we got the pleasure of being right there with him on the trip, every time he stepped to the mic. —Foster Kamer

5.Jay-Z

Solo Albums: Reasonable Doubt (1996), In My Lifetime, Vol.1 (1997), Vol.2... Hard Knock Life (1998), Vol.3... Life and Times of S. Carter (1999)

Group Albums: N/A

Biggest Hits: "Ain't No Nigga" featuring Foxy Brown (1996), "The City Is Mine" featuring Blackstreet (1997), "Can I Get A..." featuring Amil, Ja Rule (1998), "Hard Knock Life (Ghetto Anthem)" (1998), "Jigga My Nigga" (1999)

To judge Jay-Z’s body of work solely based on the albums he put out in the '90s is to eliminate his magnum opus, The Blueprint. It also means talking about Jay-Z without talking about the chipmunk soul-sample production style Just Blaze and Kanye West pioneered on that album, one that left such a lasting impact on the 2000s. And yet, despite that, Jay-Z ranks within the top five of the '90s best rappers. The work he put in during this decade laid the foundation for the mogul he was to become. And when pitted head-to-head against the material he released in the following decade, the four albums he dropped in the '90s might even surpass his overall catalog of the 2000s.

Of course, it all begins with Reasonable Doubt. Jay’s first album is a staple in the “mafioso rap” subgenre. The pairing of Jay’s then rapidfire flow with the jazzy, boom-bap production of Ski Beatz, Clark Kent, and DJ Premier resulted in an album that offered gritty street rhymes and pensive honest reflection in equal measure. For a devout few, this remains Jay’s best album.

Reasonable Doubt satisfied the purists. But after it, Jay departed from the boom-bap wheelhouse, never to truly return. In a lot of ways, this was for the best. Would Jay have been able to recreate the magic of his debut album while sticking to that same sound? Probably not. Would he have been able to become the most influential man in hip-hop? Absolutely not. Jay needed to evolve sonically to become the heir to New York’s throne after Biggie died.

The first album, In My Lifetime, Vol. 1, had a few stumbles on it, relying too much on recreating the Biggie formula by tapping into production from Diddy’s Hitmen crew. But the following year, Jay struck paydirt with Vol. 2… Hard Knock Life. The album’s title track became its second single and ultimately Jay’s most successful single until 2009’s “Empire State of Mind” topped the charts.

Meanwhile, the album’s other singles, "Can I Get A…," "Money, Cash, Hoes," and "Nigga What, Nigga Who (Originator 99)" are signature songs in Jay’s catalog. One year later, Jay closed out the decade with Vol. 3… Life and Times of S. Carter, which spawned hits like "Jigga My Nigga" and "Big Pimpin." Jay had locked in with Swizz Beatz, Timbaland, and Irv Gotti to create his own commercial sound. All three would go on to stand among the biggest producers of the following decade. Meanwhile, Jay continued to tap into the boom-bap sounds of DJ Premier to bring balance to his albums.

While Jay transitioned into a mogul in the 2000s, he created most of his best material the previous decade. —Dharmic X

4.Scarface

Solo Albums: Mr. Scarface Is Back (1991), The World Is Yours (1993), The Diary (1994), The Untouchable (1997), My Homies (1998)

Group Albums: The Geto Boys (1990) with Geto Boys, We Can't Be Stopped (1991) with Geto Boys, Till Death Do Us Part (1993) with Geto Boys, The Resurrection (1996) with Geto Boys, Da Good da Bad & da Ugly (1998) with Geto Boys

Biggest Hits: "Mind Playing Tricks on Me" with Geto Boys (1991), "Six Feet Deep" with Geto Boys (1993), "Hand of the Dead Body" featuring Ice Cube, Devin the Dude (1994), "I Seen a Man Die" (1994), "Smile" featuring 2Pac, Johnny P (1997)

Brad “Scarface” Jordan is the most underrated rapper of all time.

Scarface is a member of Houston’s Geto Boys, the rough-tough Texan trio who were pioneering gangsta rap and southern rap in the '80s, before either of those terms were part of the national lexicon. In 1991, he wrote what many people (including Kid Cudi, Bun B, and, on most days anyone would ask, me), consider to be the single best rap song ever recorded, "Mind Playing Tricks On Me." Originally intended to be a solo effort, ’Face’s harrowing examination of the depression and paranoia that can plague life in the drug game became the highlight of his group’s fourth album We Can’t Be Stopped, and displayed the breathtaking artistry and honesty that rap music, still so often maligned, was capable of. “I sit alone in my four-cornered room, staring at candles,” he says at the outset. Ten words. Is there a better, more economical depiction of mental anguish in rap? In the lyrics of any music? In poetry, ever? It’s the “four-cornered” part that does it. The emptiness, the awareness of one’s solitude in a given space. Staring at candles. It makes you shiver just typing it.

His first two solo albums were huge sellers down South, uncompromising barrages of foul-mouthed nastiness and the all-too-real-feeling horrors of Houston street life. He rhymed in a baritone; steady, relentless, all cowboy-boot tough and black-hat bad. He was about as bad as anyone’s ever sounded on the mic, in the full panoply of meaning that that term carries. Fast and furious over straight-up-and-down boom-bap beats, slow and sinister over soul-sample funk.

But rap was changing in the early ’90s. The seismic impact of Dr. Dre’s The Chronic changed the sound of the entire genre. And here’s where the assets that set Scarface apart from so many of his peers came to the fore: Consistency, musical versatility. In 1994, working with his long-time collaborator N.O. Joe, and, for the first time, with a mysterious, motorcycle-riding white guy named Mike Dean, Scarface made his solo masterpiece, The Diary. Again marked by emotional honesty and clear-eyed, unflinching vision, but set to a wider, smoother, almost orchestral sound played with live instruments, the album was the start of the most fruitful stretch of a long, prolific career. Cold, but sorrowful somehow, burdened, but deepened, by the death obsession running through them as a theme, songs like "No Tears," "I Seen a Man Die," and "Hand of the Dead Body" established Scarface as the singular voice of rap’s sense of mortality. He was 23-years-old when the album came out. He rhymed with the gravitas of an old, old man.

Next, in 1996, came the Geto Boys’ reunion album, The Resurrection. Does everybody know that this is the best Geto Boys album, a top-ten-of-the-’90s album? Does everybody know that on “Geto Boy and Girls,” over the burly bass and blues guitar cooked up with Mike Dean, when the Scarface and Willie D detail the Northside/Southside strife that had broken up the group five years before, and very nearly led to gun violence between the two and their crews, but then how they “sat down and settled their differences like men,” that this, too, is one of the pinnacle achievements of Southern rap? I feel they don’t. Or at least, this doesn’t get talked about enough. Scarface is so underrated.

Then ’Face got to flexing. The Untouchable he called his next album, in 1997, a more shimmering collection of songs, poppier maybe than anything he’d previously done, at the dawn of the shiny-suit era. (And including the poignant, lovely, "Smile"—a duet with ’Face’s friend Tupac, the first posthumous song to be released after his death.) Even with its brighter tones, though, the music was still streaked by rattlesnake-hiss percussion, still dangerous, still stunningly powerful. And then My Homies, a double-disc full of guest appearances from an impressive array of star-level talent. Tupac, Willie D, Bushwick Bill, Ice Cube, Master P, Devin the Dude, Do or Die, B-Legit, UGK, Too Short, Big Mike, Yukmouth, Menace Clan. An army of prominent gangsta rap artists, from all over the hip-hop map, heavyweights came to give dap, to show love, to get down. His peers know. Ask a rapper, they’ll tell you. No much how much respect and acclaim and admiration Scarface could ever get. Really, it would never be enough. —Dave Bry

3.Nas

Solo Albums: Illmatic (1994), It Was Written (1996), I Am... (1999), Nastradamus (1999)

Group Albums: The Firm: The Album (1997) with The Firm

Biggest Hits: "It Ain't Hard To Tell" (1994), "The World Is Yours" (1994), "If I Ruled The World (Imagine That)" featuring Lauryn Hill (1996), "Street Dreams" (1996), "Hate Me Now" featuring Puff Daddy (1999)

If 18-year-old Nasty Nas had done nothing more than show up at Large Professor's recording session one night and start poppin' shit about "waving automatic guns at nuns," "snuffin' Jesus," and so forth, he would still warrant some sort of mention in a compendium of the decade's greatest MCs. But his scene-stealing verse on Main Source's 1991 b-side "Live at the Barbeque" was nothing but a warning shot. The following year Nas got in the studio with Large Pro, DJ Premier, Pete Rock, L.E.S., and Q-TIp to create a modern masterpiece know as Illmatic.

Nearly 20 years after its release, Nas' debut album still looms large over hip-hop. Aside from exerting a profound influence over an entire generation of rappers, Nas' rhymes are studied as serious literature in universities around the world. As he pointed out in "The World Is Yours," all the words pass the margins in his book of rhymes. More to the point, his books of rhymes helped to ensure that hip-hop would never be marginalized.

According to conventional wisdom, Nas fell off after Illmatic, unable to live up to the promise of his stellar debut. There is no disputing the fact that Illmatic is a bona fide classic, having earned a rare five-mic rating in The Source at a time when the publication was truly considered the bible of hip-hop. But also, in retrospect, its follow-up shrugs off some of the slings-and-arrows that it suffered back in '94. Produced by Trackmasters with supervision by Nas' then-manager Steve Stoute, It Was Written struck a perfect balance between artistic ambition and commercial appeal. It debuted at No. 1 on Billboard's album chart on the strength of the single "If I Ruled The World" featuring another of the '90s greatest rappers, Lauryn Hill, and went on to sell four million copies on the strength of strong songs like "The Message" to "Street Dreams" to "I Gave You Power."

By this point Nas was firmly established as one of hip-hop's most important figures. His other two major releases of the decade were less consistently excellent that what came before, but both had moments of sheer brilliance. Nas slays Dr. Dre's skeletal beat on "Phone Tap" from The Firm's 1997 set, which helped usher in the era of mafiosos rap. And Nas's much-maligned 1999 solo album I Am... boasts bangers like "Nas Is Like," "Hate Me Now" featuring Puffy, and "Favor for a Favor" featuring Scarface. Perhaps Nas's quality-control meter was not quite set to Illmatic levels on records like "Dr. Knockboot," or on the entire Nastradamus album, his final release of the decade. But by that point, he had more than secured his spot as one of hip-hop's most important voices. —Rob Kenner

2.2Pac

Solo Albums: 2Pacalypse Now (1991), Strictly 4 My N.I.G.G.A.Z. (1993), Me Against the World (1995), All Eyez On Me (1996), The Don Killuminati: The 7 Day Theory (1996)

Group Albums: Thug Life: Volume 1 (1994) with Thug Life, Still I ride (1999) with Outlawz

Biggest Hits: "I Get Around" featuring Shock G, Money-B (1993), "Dear Mama" (1995), "California Love" featuring Dr. Dre, Roger Troutman (1995), "How Do U Want It" featuring K-Ci, JoJo (1995)

While 2Pac ranks high in the debate over the best rappers of all time, it's usually with an asterisk next to his name. In 1999, in a special issue about "The 50 Greatest MCs Ever," Blaze magazine opined that 'Pac (ranked at number seven) compensated for his "average rhyme skill" by captivating the world with controversy and heartfelt subject matter. Indeed, the notion that 2Pac was a mediocre rapper who was only famous because of his charisma and off-stage antics was a charge that got considerable ink when he was alive, too. In early 1995, weeks before the release of 2Pac's best album Me Against The World, Touré wrote in the Village Voice that 'Pac was "merely an average vocalist and lyricist, even by West Coast standards."

Average. It's a peculiar criticism to hear applied so regularly to someone widely known as one of the best rappers of all time. New York hip-hop tradition demands that a rapper master all manner of word play (similes, double-entendres, puns, metaphors) to be considered one of the greats. 2Pac wasn't interested in being semantically clever, preferring a more straight-forward approach that emphasized emotion and wisdom over pure lyrical style. "This ain't just a rap song, [it's] a black song/Tellin' all my brothers get they strap on," he rhymed on 1993's "Holler If Ya Hear Me."

At its core, hip-hop is an endlessly inventive post modern exercise. But 'Pac represented an alternative, a plain-spoken realism that was aching to be heard outside of NYC's jurisdiction. "Being in Marin City was like a small town, so it taught me to be more straight foward with my style," 2Pac told Davey D in a 1991 interview. "Instead of being so metaphorical with the rhyme, I was encouraged to go straight at it and hit it dead on and not waste time trying to cover things." The formal simplicity left room for his searing intensity to shine through, free from gimmicky distractions.

2Pac believed that by avoiding winking punchlines and pretentious wordplay, his music would be more meaningful to the outcasts of America. "This is for the masses, the lower classes, the ones you left out/Jobs were given, better livin', but we were kept out," he spit on "Words of Wisdom" from his debut album. Throughout all his stylistic changes, it was this goal of representing the real, neglected America that stayed constant. 'Pac was an intellectual who believed everyone who lives through struggle had something important to say, even criminals. And he eventually became one to prove his point. "I never had a record until I had a record deal," he said.

His blunt approach cast a wider net than so-called "lyrical" hip-hop, inspiring a jaded generation to make rap music without worrying about the critics. "It's all sort of entertaining, but 2Pac is not an especially deep thinker," Jonathan Gold of the Los Angeles Times said in 1993 while reviewing his second album, Strictly 4 My N.I.G.G.A.Z. But as the album title implied, Tupac's music was not meant for Jonathan Gold. Far from an asterisk, being an "average" rapper was 'Pac's secret weapon, a trojan horse designed to inspire the uninspired. —Brendan Frederick

1.The Notorious B.I.G.

Solo Albums: Ready to Die (1994), Life After Death (1997), Born Again (1999)

Group Albums: Conspiracy (1995) with Junior M.A.F.I.A.

Biggest Hits: "Juicy" (1994), "Big Poppa" (1994), "One More Chance" (1994), "Hypnotize" (1997), "Mo Money Mo Problems" featuring Ma$e, Puffy Daddy, Kelly Price (1997)

“I want people to buy [my new] album ... and just straight up say, ‘Yo, he’s the best. He’s the best ever. He’s the best that ever did it.’ That’s what I’m looking for. I want my props. ’Cause they slept on me. I read [what people write and say] and they give me my props as being that solo emcee that blew up from the East Coast: But they don’t give me my props like, ‘Yo, Big be straight dicin’ niggas on the mic! On the rhyme side, he’s nice!’ They don’t really look at me like that.”

I remember reading Chairman Mao's story about the Notorious B.I.G. in The Source magazine in 1997, just before the Life After Death album came out, just before the Brooklyn rap great was murdered in California, and being struck by the quote above. The hubris! Biggie had only released one album at that point, 1994's Ready to Die. It was good. It was better than good. It was great! But, man, was this young dude really justified in using words like "best ever." He's saying he's dicin' nicer than Rakim?! FOH!

But then the new album came out. It was a double album. A sprawling, diverse, incredibly ambitious collection of songs running the gamut from true-school traditionalist boom-bap like "Kick in the Door" to picture-perfect radio fare like "Mo' Money Mo' Problems," slick, funny story-rap like "Got a Story to Tell" to dark, chilling epics like "Niggas Bleed" and "Long Kiss Goodnight." It took us awhile to digest. The process, the proper perspective, was made more difficult by the terrible, crazy circumstances surrounding this music. Namely: Its author's murder, the second such tragedy hip-hop had endured in the span of six month, and the hysteria rap was thrown into thereafter. No one knew which way was up and which way was down for a while. We were all in shock, in a daze.

As time wore on, though, the emotional wounds healed. Only then were we able to look at and listen to, this work that this artist had left us with clearer eyes, ears. It was nothing short of a masterpiece, this album. Biggie's growth as a rapper, his maturity, his vision, his scope—I'm not sure we'd seen anything like it before. And considering it alongside the raw, less-polished power of Ready to Die, looking at what was now, sadly, we knew, this artist's total ouvre, we started to see that, yes: he was different. Special. Better. He was better than everyone. Better than anyone had ever been before.

He'd proved it. It's not bragging if you can back it up. —Dave Bry