We filtered through 45 years of the genre’s existence, picked out the 20 best, and ranked them with regard to overall greatness.

In order to determine the greatest year in hip-hop history-as objectively as possible-we filtered through 45 years of the genre’s existence, picked out the 20 best, and ranked each one with regard to overall greatness. That greatness has been decided according to a few key guidelines. Among other factors, our contenders will be measured by five (mostly objective) categories:

  1. Certified Classics: The number of classic albums released that year. Since there’s no precise definition of what qualifies as a “classic,” we’ll focus on those projects that were either a) historically significant and/or influential, b) critically acclaimed, or c) an unprecedented commercial success.
  2. Essential Projects: The number of albums released that year which were great, though not-quite classics. In other words, those that were memorable.
  3. Apex Rappers: The handful of all-time great MCs who were operating at the peak of their powers that year.
  4. Breakout Stars: The number of up-and-coming rappers who exploded (or were on the precipice of a career breakthrough) that year.
  5. Watershed Moments: What is the year’s defining moment? Landmark beef? Two rappers battling for the throne? A changing of the guard?

Let’s get to it.

See Also: PART 1 (20-16) | PART 2 (15-11) | PART 3 (10-6)

5. 1998

Certified Classics: OutKast, Aquemini; Lauryn Hill, The Miseducation of Lauryn Hill; DMX, It’s Dark and Hell Is Hot; Juvenile, 400 Degreez; JAY-Z, Vol. 2… Hard Knock Life; Big Pun, Capital Punishment; Gang Starr, Moment of Truth

Essential Projects: Black Star, Mos Def & Talib Kweli Are Black Star; Fat Joe, Don Cartagena, The Lox, Money Power & Respect

Apex Rappers: JAY-Z, Lauryn Hill, André 3000

Breakout Stars: DMX, Big Pun, Juvenile

'98 was a pivotal moment for hip-hop, one that found the genre entering the first full year without titans 2Pac and Biggie. Following Biggie’s death in March ‘97, the Bad Boy Machine kept churning out hits, with both its bubblegum sound and shiny suit style cementing itself as the face of hip-hop. Still, it couldn’t last; not without a true superstar spearheading the movement.

With the rap game facing a full-blown identity crisis, the hip-hop gods gifted a shot of adrenaline in the mold of a bubbling underground rapper who made a name for himself on the battle rap circuit. DMX touched down in the first quarter of ‘98 as the rap game’s savior, steering the genre away from Diddy’s Jiggy era in favor of a hardcore approach that was equal parts raw and refreshing. In May, his debut It’s Dark and Hell Is Hot opened at the top of the Billboard 200; then, seven months later, he did it again with Flesh of My Flesh, Blood of My Blood, becoming the second rapper ever to have two albums released in the same calendar year debut atop the charts.

DMX wasn’t the only rapper that year to drop a classic debut, though. Bronx native Big Pun, who had come up alongside Fat Joe in the mid-1990s, released the shining star on his resume with his breakout LP Capital Punishment; Lauryn Hill, two years after entering the zeitgeist on the Fugees' 1996 debut, The Score, crafted an all-time musical masterpiece with her first solo offering, The Miseducation of Lauryn Hill; and Bad Boy’s The Lox, who’d gained exposure on Life After Death and label-head P. Diddy’s 1997 LP No Way Out, went Platinum with their debut, Money, Power & Respect.

By the summer of ‘98, the rapper everyone picked to fill Biggie’s spot atop the throne, JAY-Z, had been replaced by DMX. After failing to make the leap from critical acclaim to commercial success on his first two albums (1996’s Reasonable Doubt and 1997’s In My Lifetime, Vol. 1), Jay needed to evolve; instead, producer The 45 King gift-wrapped him a smash hit by way of the Annie-sampled “Hard Knock Life.” Released as the first single from his third album, Vol. 2... Hard Knock Life, the track peaked at No. 15 on the Billboard Hot 100, becoming Jay’s most successful single to date. That September, the success of “Hard Knock Life” helped JAY-Z capture his first No. 1 album, as Vol. 2 debuted atop the Billboard 200, minting him a pop star in the process. After the dust settled, JAY-Z had taken over Biggie’s mantle as the King of New York, and, more importantly, cemented his status as the Best Rapper Alive.

On the same day that Vol. 2 hit stores, OutKast released their third album, Aquemini. It was a landmark album for hip-hop, becoming the first Southern LP to earn a coveted five-mic score from The Source. The project advanced the genre to a place void of established notions, inspiring an entire generation of artists like Kanye West and Kendrick Lamar. Before it did all that, though, it secured Atlanta, and the rest of the South, a spot alongside New York and Los Angeles at hip-hop’s big boy table.

Roughly 500 miles southwest of Atlanta, another hip-hop empire was rising up in New Orleans. At the time, Cash Money Records was well-known in and around the Southern hip-hop scene, but in late ‘98, Bryan "Birdman" Williams' label rose to national prominence with the release of star player Juvenile’s third studio album, 400 Degreez. Rap music had never sounded so futuristic, as evidenced by the LP’s lead single, “Ha,” which paired New Orleans bounce music with Mannie Fresh’s synths and Juvenile’s singular voice and rapping ability. But it was the album’s second single, “Back That Azz Up,” that changed everything, launching Cash Money and its army into the upper echelon of hip-hop notoriety.

4. 1993

Certified Classics: Wu-Tang Clan, Enter the Wu-Tang (36 Chambers); Snoop Dogg, Doggystyle; A Tribe Called Quest, Midnight Marauders; Souls of Mischief, 93 ’til Infinity; De La Soul, Buhloone Mindstate; Black Moon, Enta da Stage

Essential Projects: 2Pac, Strictly 4 My N.I.G.G.A.Z…; KRS-One, Return of the Boom Bap; 8Ball & MJG, Comin’ Out Hard; Digable Planets, Reachin' (A New Refutation of Time and Space); Onyx, Bacdafucup; Cypress Hill, Black Sunday

Apex Rappers: Q-Tip, Snoop Dogg, Treach

Breakout Stars: 2Pac, Method Man, Raekwon

The Chronic was conceived in the summer of 1992 and hit stores that December, but the project belongs to 1993. That’s the year it became a pop culture phenomenon when hip-hop felt the full effects of Dr. Dre’s G-funk and Snoop Dogg’s unending flow. After entering the charts at the top of the year, the LP spent the first eight months in the top 10 of the Billboard 200, eventually peaking at No. 3. Meanwhile, Dre and Snoop stayed in heavy rotation on the radio, with the album’s three hit singles: “Nuthin' but a ‘G’ Thang,” “Fuck wit Dre Day,“ and “Let Me Ride.”

Following a quiet spring and summer, hip-hop exploded in the fall ‘93. The nine-week window between September 21 and November 16 featured the release of five of the greatest rap albums all-time. De La Soul kicked things off on September 21 with the group’s third album Buhloone Mindstate. The follow-up to ‘88’s 3 Feet High and Rising and ‘91’s De La Soul Is Dead was the group's third straight classic, a muted record which mirrored the end of their mainstream relevance. One week later, on September 28, came 93 ‘til Infinity, the debut album from Souls of Mischief. Unlike their West Coast contemporaries, the Oakland group chose jazzy loops over gangsta rap, spearheading the Bay Area’s ascension to regional hip-hop staple.

Yet both albums were mere appetizers to arguably the greatest month in rap history, which began with the best release date ever, November 9. That day featured two albums that are surefire first-ballot rap hall-of-famers, and arguably two of the 20 best hip-hop LPs ever: Wu-Tang Clan’s debut album, Enter the Wu-Tang (36 Chambers) and A Tribe Called Quest’s third album, Midnight Marauders. Going into that fateful Tuesday, all eyes were on Tribe, who was two years removed from cementing its legacy with one of the greatest albums of all time, The Low End Theory. While Tribe didn’t quite top their first classic, Midnight Marauders showcased Q-Tip and Phife Dawg’s progression, both sonically and on the mic. At the same time, Wu-Tang quietly submitted an iconic project of their own, one that, in hindsight, served as the beginning of the second golden age of New York hip-hop.

Just two weeks after the East Coast released the pair of classics, the rapper-producer duo who’d been dominating the hip-hop landscape since the final weeks of ‘92 returned with the most anticipated debut album in hip-hop history, Snoop Doggy Dogg’s Doggystyle. Like The Chronic, Snoop’s debut was an instant classic, debuting atop the Billboard 200 and moving 806,000 copies in its first week to become the fastest-selling rap album ever. Backed by Dre’s signature G-funk sound and Snoop’s lazy drawl, Doggystyle became inescapable, scoring a pair of Hot 100 top-10 hits with “Gin and Juice” and “Who Am I (What's My Name)?” By 1994, the barely-out-of-high-school Snoop Dogg jumped into the upper echelon of hip-hop and established the West Coast as the genre’s most powerful region.

3. 1996

Certified Classics: 2Pac, All Eyez on Me; JAY-Z, Reasonable Doubt; OutKast, ATLiens; Fugees, The Score; UGK, Ridin' Dirty; Ghostface Killah, Ironman

Essential ProjectsNas, It Was Written; Busta Rhymes, The Coming; Redman, Muddy Waters; Mobb Deep, Hell on Earth; M.O.P., Firing Squad; 2Pac, The Don Killuminati: 7 Day Theory; Lil’ Kim, Hard Core; Kool Keith, Dr. Octagonecologist; De La Soul, Stakes Is High; The Roots, Illadelph Halflife; DJ Shadow, Endtroducing...

Apex Rappers: 2Pac, The Notorious B.I.G., Nas

Breakout Stars: JAY-Z, Lauryn Hill, Ghostface Killah

The deal that would alter the course of hip-hop history was staged 300 miles north of Manhattan inside Clinton Correctional Facility, where 2Pac was serving up to four and a half years for two counts of sexual assault. Nine months into the rapper’s sentence, head of Death Row Records Suge Knight came to him with an offer: Knight would pay his $1.4 million bail, but Pac would have to sign a three-album deal with Death Row. On October 12, 1995, Pac signed on the dotted line and walked out of prison a free man. It was a deal with the devil, both the best and worst decision he ever made. On paper, though, the partnership was a match made in heaven, pairing hip-hop’s most outspoken thug with its leading villain and head of the most controversial record label the rap game had ever seen. More than anything, though, Pac and Death Row shared a common vision: wreak havoc and eviscerate all enemies.

From the moment 2Pac was sprung from jail, he recorded at a frenetic pace. Less than 24 hours after his release, he was at Can-Am studios in Los Angeles putting the finishing touches on “Ambitionz Az a Ridah,” a song that would eventually open his forthcoming album, All Eyez on Me. And within two weeks, the sprawling, 27-track LP was finished. His incredible work ethic paid dividends that February, when All Eyez on Me debuted at No. 1 and moved 566,000 copies in its opening week, achieving 5x Platinum certification by April. By the summer of 1996, Pac was a megastar, notching back-to-back No. 1 singles on Billboard’s Hot 100 with “California Love” and “How Do U Want It,” and laying waste to arch-rival Biggie on arguably the greatest diss track of all time, “Hit 'Em Up.” At that point, the Best Rapper Alive discussion was over, with Pac firmly established as the quintessential commercial star in hip-hop.

While 2Pac was the undisputed champion of ‘96, JAY-Z crafted the best album of the year with his debut LP, Reasonable Doubt, released in late June. At the time, it was criminally overlooked in favor of another album set to drop one week later: the most anticipated release of the year and follow-up to the best debut of all time, Nas’ It Was Written. Although Nas’ sophomore LP cemented him as Biggie’s equal, Reasonable Doubt turned out to be the consensus fan favorite. With hindsight, there’s not much of a competition between the two projects; while It was Written suffers, somewhat unfairly, in the shadow of Illmatic, Reasonable Doubt is commonly accepted as one of the best debut albums of all time.

'96 is remembered as the only year that featured 2Pac, Nas, Biggie, and JAY-Z all at the peak of the powers, but it also included an endless array of certified classics from their peers. OutKast delivered its first masterpiece, ATLiens, forcing the culture to accept Atlanta as a Mecca-in-the-making. The Fugees brought the world potential superstars Lauryn Hill and Wyclef Jean on their sophomore album, The Score. Ghostface Killah dropped Ironman, the last of the classic Wu-Tang solo offerings; rookies Busta Rhymes and Lil’ Kim dropped their strongest LPs, The Coming and Hard Core, respectively. And UGK usurped the Geto Boys as the Kings of Texas with their first classic, Ridin’ Dirty.

2. 1994

Certified Classics: Nas, Illmatic; The Notorious B.I.G., Ready to Die; Scarface, The Diary; OutKast, Southernplayalisticadillacmuzik; Common, Resurrection; Gang Starr, Hard to Earn

Essential Projects: Warren G, Regulate…G Funk Era; Bone Thugs-N-Harmony, Creepin on ah Come Up; Method Man, Tical, Gravediggaz, 6 Feet Deep; UGK, Super Tight; Pete Rock & CL Smooth, The Main Ingredient

Apex Rappers: Nas, The Notorious B.I.G., Scarface

Breakout Stars: Common, André 3000, Pimp C

By 1994, the West Coast had been in power for nearly six years. Home to the two most popular sub-genres in hip-hop (Gangsta rap and G-funk), the best producer alive (Dr. Dre), the best rapper alive (Snoop Dogg), and the former best rapper alive (Ice Cube), Los Angeles had finally toppled New York to earn the right to be called the Mecca of hip-hop. And in recent years, whenever New York appeared to pull hip-hop back to its birthplace, the West Coast countered: most recently, in November ‘93, when Doggystyle obliterated everything in its path just two weeks following the release of two East Coast classics, Enter the Wu-Tang and Midnight Marauders.

From the jump, '94 started just as the previous year did. Dre and Snoop were atop the charts, as Doggystyle re-entered at No. 1 on the Billboard 200 in January, before its second single, “Gin and Juice,” simultaneously entered the top ten of the Hot 100 and climbed to No. 1 on the Hot Rap Songs chart in March. The album’s dominance continued to widen the gap between the West and East, with all eyes fixated on New York’s ongoing decline.

Well, at least that’s what it looked like from a distance. For those surveying the scene within the trenches, checking the pulse of New York hip-hop was hardly necessary. The second coming of Rakim had already arrived in the form of Nas, a 19-year-old rapper who’d been drawing buzz ever since his scene-stealing verse on Main Source’s 1991 single “Live at the BBQ.” So, if anything, ‘94 would be an official coronation. Not a funeral. That April proved East Coast rap know-it-alls clairvoyant when Nas’ debut Illmatic hit planet hip-hop like a meteor. Upon its release, the LP was met with widespread critical acclaim and certified an instant classic. Fulfilling the prophecy, the album cemented Nas as the Best Rapper Alive, and the first New York-based MC to hold the title since Q-Tip in 1991.

Five months later, in the shadow of Nas emerged Biggie, who released his debut Ready to Die that September. Ready to Die earned approval on critical and commercial levels, and continued to build momentum on the back of hit singles “Juicy,” “Big Poppa,” and “One More Chance.” By the end of the year, rap fans considered the album a classic, minting Biggie a superstar in the process. More than anything, though, New York was back. Better than ever, even. For the first time since Rakim and Big Daddy Kane’s power struggle in the late '80s, the Big Apple was home to the two best rappers alive, who’d finally given the East Coast an answer to the West Coast’s recent pair of masterpieces with two of its own.

Oddly enough, New York’s revival coincided with a significant shift underway between the coasts. Down South, the seeds were planted for the region’s rise: In Houston, Scarface got his first taste of national stardom with the release of his third album, The Diary. His first classic without the Geto Boys, the LP finally pushed him into the Best Rapper Alive conversation, while paving the way for Texas' up-and-coming duo, UGK. In Atlanta, the emergence of OutKast foreshadowed the city’s potential as a hip-hop power, as André 3000 and Big Boi’s debut, Southernplayalisticadillacmuzik, became an enormous success. Meanwhile, up north, Chicago and Cleveland proved that the Midwest had something to say, with Common’s Resurrection and Bone Thugs-N-Harmony’s Creepin’ on Ah Come Up, respectively.

1. 1988

Certified Classics: Public Enemy, It Takes a Nation of Millions to Hold Us Back; N.W.A, Straight Outta Compton; Slick Rick, The Great Adventures of Slick Rick; Big Daddy Kane, Long Live the Kane; EPMD, Strictly Business; Eric B. & Rakim, Follow the Leader; Jungle Brothers, Straight Out the Jungle; Biz Markie, Goin Off; Ultramagnetic MCs, Critical Beatdown; Eazy-E, Eazy-Duz-It; Boogie Down Productions, By All Means Necessary

Essential Projects: Too $hort, Life Is…Too $hort; MC Lyte, Lyte as a Rock; Marley Marl, In Control, Volume 1; Ice-T, Power; DJ Jazzy Jeff & The Fresh Prince, He’s the DJ, I’m the Rapper

Apex Rappers: Rakim, Slick Rick, Chuck D

Breakout Stars: Big Daddy Kane, Eazy-E, Ice Cube

The single greatest and most influential year in the history of hip-hop is 1988, a year which changed the genre forever and established the blueprint for the next 30 years of rap music. Here’s a closer look at five significant milestones:

The explosion of West Coast hip-hop. On August 8, 1988, N.W.A released its debut album, Straight Outta Compton. The LP popularized gangsta rap and made Dr. Dre the hottest producer in rap, Ice Cube the best rapper alive, and Eazy-E the face of gangsta rap. More than anything, though, by introducing the world to Compton, CA-and, moreover, the larger region of South Central Los Angeles-Straight Outta Compton shifted hip-hop’s balance of power to the West Coast, away from New York. And really, if not for the album, Dr. Dre doesn’t become a superstar, Snoop Dogg goes through life an undiscovered talent, and Suge Knight’s Death Row Records doesn’t reach the level of power that helped make 2Pac an icon. In that case, you can forget about Dre co-signing legends like Eminem, 50 Cent, The Game, and Kendrick Lamar.

The rise of socially conscious, political rap. Backed by their profanity and violent lyrics, N.W.A became pioneers for militant rap during the summer of 1988 with songs like “F*** the Police,” but two months earlier, in June, Public Enemy set out to make the hip-hop equivalent of Marvin Gaye's classic What's Going On with their second album, It Takes a Nation of Millions to Hold Us Back, arguably the greatest rap album of all time. Backed by the Bomb Squad’s chaotic production style, Public Enemy cemented itself as the icons of socially conscious, political rap. The album remains a landmark moment not only for hip-hop but for all of recorded music. 

The evolution of storytelling. After a career-defining feature on Doug E. Fresh’s 1985 single “La-Di-Da-Di,” Slick Rick ascended the throne with his debut album The Great Adventures of Slick Rick, released on November 3, 1988. English accent in tow, Slick Rick pushed storytelling to new heights on landmark singles “Children’s Story” and “Hey Young World.” And with his slapstick style, introduced singsong cadences to the genre, which paved the way for its next biggest star, Snoop Dogg.

The emergence of hip-hop’s first crossover superstar. In 1987, Rakim cemented himself as the game’s first undisputed Best Rapper Alive by way of his innovative and unmatched lyricism. But in the summer of 1988, Big Daddy Kane emerged as a rival to the crown. With the release of his debut LP, Long Live the Kane, that June, Big Daddy Kane became hip-hop’s biggest sex symbol and first crossover star since LL Cool J. Even more, he was a better lyricist who possessed a rougher persona, one that paved the way for fellow Brooklyn superstars, Biggie and JAY-Z.

In short, the simultaneous breakthroughs of N.W.A, Public Enemy, Slick Rick, Big Daddy Kane, and more pushed hip-hop further into the mainstream than ever before, while charting the course for the genre’s next decade of stars. 1988 is the greatest year in rap history because it’s the moment everything in hip-hop changed.

See Also: PART 1 (20-16) | PART 2 (15-11) | PART 3 (10-6)

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