The 30 Greatest Months in Rap History

Perhaps no type of music makes quite as much of a fuss about the calendar as hip-hop. Diddy once declared that he'd be in a position of power "from now 'til the year 3000." Jay-Z has rapped about how he held rap fans down for "six summers." It's a very time conscious genre, with artists who are incredibly self-aware about the value of their work at the time of its release, as well as its legacy for the future.

The only thing: Rap's obsession with the correlation between time and accomplishments tends to skew towards years—and any rap nerd can list off incredible years in hip-hop: 1988, 1994, 2000. We decided to take a closer a look, and examine what happened during particular months. You know that month when both Illmatic and Southernplayalisticadillacmuzik dropped (hint: It was this month, 19 years ago)? It's time to pit moments like that against other landmark spans of time in hip-hop, and find out where the cards fall.

Our current month, April 2013, has been a hell of a ride. Kid Cudi and Tyler, the Creator dropped albums. Drake hopped on the radio and dissed Chris Brown. Coachella took over our Instagram feeds for two weekends. Kanye West flew a flock of artists to Paris to work on music. The news cycle never took a break. If there's any time to talk about the impact of an awesome month, it's now.

These are The 30 Greatest Months in Rap History.

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30. October 2000

Notable Events:
- The NBA beefs with Allen Iverson over his rap song
- Jedi Mind Tricks' Violent By Design is released on 10/3/2000
- M.O.P.'s Warriorz is released on 10/10/2000
- Ja Rule's Rule 3:36 is released on 10/10/2000
- Reflection Eternal's Train of Thought is released on 10/17/2000
- Ludacris' Back for the First Time is released on 10/17/2000
- Jay-Z's The Dynasty: Roc La Familia is released on 10/31/2000
- Binary Star's Masters Of The Universe is released on 10/31/2000
- OutKast's Stankonia is released on 10/31/00

October 2000 was one of those months where, depending on what part of the country you were in, the headlines were dramatically different. In New York, Jay-Z’s The Dynasty: Roc La Familia took the sheen of Vol 3… and amplified it to the nth power: No longer were rappers-with-oil-money-rapped fantasies enough, but songs now had to sound like they were produced with oil money, too.

Back in Brooklyn not too far from Hov’s origin, M.O.P. knew they were about to get every block party, fight, and teenage locker room turnt up as they readied Warriorz for release, and Ja Rule got ready to occupy every teenage bedroom and radio with Rule 3:36, his attempt at pop stardom that went a little too well. Talib Kweli—coming off of one of the hottest collaboration albums in rap via Black Star—teamed up with producer Hi-Tek to form Reflection Eternal and deliver one of the greatest OkayPlayer 1.0-era rap albums (and one of the most underrated collaborations in rap history) with Train of Thought.

In Philadelphia, the talk wasn’t OkayPlayer so much as not-OK Allen Iverson beefing with the NBA over his homophobic raps and the release of next-next-next level rap group Jedi Mind Tricks’ Violent By Design. Even further off the mainstream hip-hop grid was Pontiac, Michigan’s Binary Star, who dropped their Masters Of The Universe at the end of the month.

But in the fall of 2000, the action was spelled A-T-L: Hotlanta DJ-turned-MC Cris Bridges turned out his first proper studio release, a hypercharged thugsplosion that was the spiritual rap album descendant of Richard Pryor’s That Ni**er’s Crazy, which isn’t to say it wasn’t serious: It was. The city was on something different. And everyone knew it when, on Halloween, Atlanta produced no tricks, just treats, as OutKast released their highly-anticipated Aquemini follow-up Stankonia, the likes of which nobody had ever heard before in hip-hop, and nobody ever would again—it would be the group’s last, full proper collaboration (subsequent follow-ups were either repackaged material or barely involved both members). —Foster Kamer

29. March 1987

Notable Events:
- Boogie Down Productions' Criminal Minded is released on 3/3/1987
- DJ Jazzy Jeff & The Fresh Prince's Rock The House is released on 3/19/1987

And it came to pass in the seventh year of the Reagan Administration that a crack cocaine epidemic grabbed inner-city America by the neck. Although L.A. was the epicenter, the rock plague spread across the country, devastating a generation and turning many urban communities into zombie-filled war zones. In March of that year, rap duos from two East Coast cities released debut albums that were diametrically opposed in every possible way, yet each marked the beginning of a brilliant career. First up was Boogie Down Productions' Criminal Minded, in which The Blastmaster KRS-One and DJ Scott LaRock put the realities of daily life in the South Bronx during the crack era on wax in a way never before imagined. Songs like "9MM Go Bang" and "The P Is Free" left nothing to the imagination, and the beats (thanks to an under-the-radar production assist from Ced Gee of Ultramagnetic MCs) were even more relentless than The Blastmaster's braggadocios rhymes.

On the opposite end of the spectrum stood DJ Jazzy Jeff and The Fresh Prince, whose light-hearted debut album Rock The House dropped a couple weeks after Criminal Minded. Their LP was all about fun, and thus, 100% devoid of social commentary (unless you count the I Dream of Jeannie theme song–sampling hit "Girls Ain't Nothing But Trouble" or the lesser-known answer record "Guys Ain't Nothing But Trouble" featuring Ice Cream Tee). Will and Jeff's native Philadelphia was just over 100 miles southwest of the Bronx, but you'd think it was another planet if it weren't for Schooly D's alternate take of life in the illadelph. The Fresh Prince made a conscious decision to use his story-telling skills to entertain rather than inflame, and that instinct has served him well as he went on to be the first rapper to win a Grammy or star in a TV show. Today he's one of the highest paid matinee idols of all time and Jazzy Jeff remains one of the greatest DJs ever to touch a turntable. Scott LaRock would be murdered shortly after the release of Criminal Minded. As for KRS-One? He went on to become a philosopher, author, lecturer—all while maintaining his status as an MC-in-Good-Standing over 26 years after his debut. —Rob Kenner

28. February 2004

Notable Events:
- OutKast's Speakerboxxx/The Love Below wins Grammys for Best Rap Album and Album of the Year on 2/8/2004
- Kanye West's The College Droput is released on 2/10/2004
- Chamilionaire's King Koopa: The Mixtape Messiah is released on 2/15/2004
- Chappelle's Show airs the first Lil Jon skit on 2/25/2004

After Jay-Z's "retirement" in 2003 with The Black Album, it was pretty clear that hip-hop was all over the place. Not that it was a bad thing: Rap was going through a serious wall-to-wall renovation thanks to the Internet. For example, there was once a time when mixtape output like Chamillionaire's King Koopa: The Mixtape Messiah (a triple album, the first third of which was almost entirely, obsessively dedicated to talking shit on Mike Jones) was a weird, outlying novelty. At the same time, mainstream music consumers increasingly embraced rap as they found themselves burned out on the boring, lukewarm rock pushed on them by major record companies.

So when Atlanta's greatest rap act went avant-garde pop, they were rewarded for it: OutKast won the Album of the Year for Speakerboxxx/The Love Below at the Grammys in 2004, and it was neither a surprise nor a tidal shift so much as a long time coming. Rap was a part of mainstream pop culture in a way it had never been before. For example, take Chapelle's Show airing the first Lil Jon skit, which resulted in people of all colors screaming Lil Jon's trademark "YEEEAH!" and "OKAAAYYYY!" across campuses, bars, and schoolyards all over the world (Lil Jon ended up on the show, in on the joke himself). But if the world thought it had seen rap's relationship to pop culture change dramatically after OutKast's creative victory, that seemingly loud moment in rap had nothing on what happened only two days later, when Kanye West's The College Dropout dropped, the first volley in a one-man assault on rap and pop culture that would dominate the next decade. —Foster Kamer

27. November 2003

Notable Events:
- Cam'ron and Dame Dash appear on The O'Reilly Factor on 11/12/2003
- G-Unit's Beg for Mercy is released on 11/14/2003
- Jay-Z's The Black Album is released on 11/14/2003
- Immortal Technique's Revolutionary Vol. 2 is released on 11/18/2003

2003 was, in general, a banner year for hip-hop. Looking back, November, especially, appears as an amalgamation of that time's greatest movements. Jay-Z had established himself as a strong contender for Greatest Rapper of All Time, and right at his peak, pulled the rug out from under us and announced his retirement. This resulted in what was presumed to be his final album, The Black Album—a project regarded as a classic for its content as much as for the momentous atmosphere surrounding its release. On the same day, 2003's best-selling rapper, 50 Cent, released Beg for Mercy with his G-Unit crew. The album had its own hit singles in addition to 50's, and sold nearly as much as The Black Album, a testament to 50's mainstream appeal that year. 2003 also marks a massive year for Cam'ron and his crew, the Diplomats. They'd already made an impact with their debut crew LP earlier in the year, and Juelz Santana was on an impressive solo run as well. But Dipset's greatest contribution to culture in this particular month was Killa Cam and Dame Dash's appearance on The Bill O'Reilly Factor, on notoriously right-wing network FOX News. On the underground tip, Immortal Technique made waves with his landmark release, Revolutionary Vol. 2. During that month, there was truly something for everyone. —Ernest Baker

26. November 2004

Notable Events:
- Eminem's Encore is released on 11/12/2004
- Lil Jon & The East Side Boyz's "Lovers and Friends" (feat. Usher and Ludacris) is released on 11/30/2004
- T.I.'s Urban Legend is released on 11/30/2004
- Nas' Street's Disciple is released on 11/30/2004

With the growing strength of the Internet—and the subsequent demise of album sales—Eminem found a way to outmaneuver anyone out to pirate his fourth album, Encore, by dropping it four days ahead of schedule. While it sold over 710K and debuted at No. 1, its most notable impact was in digital sales, becoming the first album to sell 10K in one week. But in comparison to Eminem's previous albums, Encore didn't stand tall; Eminem later admitted that his sustance addiction at the time affected the caliber of the work as a whole. It became the only Eminem album to be nominated for a Grammy for Best Rap Album and not win.

Later that month, Nas released his seventh album, Street's Disciple, which debuted at No. 5 on the charts. The double album was a solid effort, with notable production and a characteristic variety of conscious and political rhymes—but it was routine work for Nas at that point. Where Nas' material seemed lacking challenges, T.I. made real strides on his third album, Urban Legend, with the lead single "Bring Em Out" becoming his first top-10 hit. Adding to Legend: It was an album T.I. recorded while in a work-release program for probation violation. It wouldn't be long before he sat alone on the throne as King of da South. -Lauren Nostro

25. November 1998

Notable Events:
- Juvenile's 400 Degreez is released on 11/3/1998
- Belly is released nationwide on 11/4/1998
- Beastie Boys' "Body Movin'" is released on 11/5/1998
- Method Man's Tical 2000: Judgement Day is released on 11/17/1998
- DMX's "Slippin'" is released on 11/27/1998

Given the release of the Beastie Boys' second single from Hello Nasty, "Body Movin," you could easily mistake November 1998 for a lighthearted month in rap history. It was anything but. There was DMX's "Slippin'", which might have a sample from Grover Washington's Feels So Good, but was also a dark first single from Flesh of My Flesh, Blood of My Blood. The ever-apocalyptic Method Man's Tical 2000: Judgement Day had already dropped earlier that month. And at the beginning of the month was a bright spot that emerged from one of the poorest, most violent hoods in the south: Juvenile's 400 Degreez. The very next day—almost as if rap were making some kind of point about whatever was in the air—one of the greatest (and most weirdly morose) movies in the hip-hop canon, Hype Williams's Belly, found its way to theaters. Among its stars? Method Man and DMX, of course. -Foster Kamer

24. November 1995

Notable Events:
- Eightball & MJG's On Top of the World is released on 11/1/1995
- GZA's Liquid Swords is released on 11/7/1995
- The Pharcyde's Labcabincalifornia is released 11/14/1995
- Goodie Mob's Soul Food is released on 11/17/1995
- Group Home's Livin' Proof is released 11/21/1995

The first seven days of November 1995 saw two distinct visions for the future of hip-hop. GZA's Liquid Swords essentially looked backwards. GZA was a golden-age MC who had a failed deal with Cold Chillin' Records before finding success with the Wu-Tang Clan. His album Liquid Swords was one of the more New York-centric releases in an era where NYC dominated the rap conversation. His rhymes all took place on the chessboard of the streets of Shaolin and sometimes Brooklyn. His cadence was distinctly old school, too. When those things combined, Liquid Swords stood as a testament to classic New York rap in the midst of one the greatest stretches of NYC hip-hop.

Meanwhile, Goodie Mob's Soul Food made the same case that OutKast's Southernplayalisticadillacmuzik had made the year before: The South had something to say. But they weren't OutKast clones; Goodie Mob also incorporated the South's rich musical history with Arrested Development's conscious thought to create a hip-hop style from Atlanta that was lauded nationwide. This was a harbinger of the future of rap, as Southern hip-hop would not only continue to grow in the coming decades, but the epicenter of commercial hip-hop would also eventually move to Atlanta.

The month's other two big releases would mimic these trends. Group Home's Livin' Proof dropped and was considered a classic in some circles, with superior production from DJ Premier saving the second-rate rhymes of the group. Eightball & MJG's On Top of the World had the opposite problem, however. Although T-Mix was a perfectly competent producer, he wasn't a dynamic visionary like Premier or Organized Noize, so his beats weren't quite enough to carry Eightball & MJG to the heights Goodie Mob reached later in the month. -Insanul Ahmed

23. March 1989

Notable Events:
- De La Soul's 3 Feet High and Rising is released on 3/3/89
- Kool G Rap and DJ Polo's Road To The Riches is released on 3/14/89
- Geto Boys' Grip It! On That Other Level is released on 3/12/89

March 1989 was a weird one. In an era when major rap releases—be they anticipated albums or hyped debuts—weren't packed like sardines into calendar months yet, you might not find a weirder combination than the Spring of ’89: De La Soul's 3 Feet High and Rising was the next new thing, a critical and commercial success that was as unlikely an emergence in rap as the part of New York it emerged from: Long Island.

Not far from L.I., another March ’89 milestone had an unlikely breeding ground: Corona, Queens, the home turf of the Juice Crew's member-of-the-moment Kool G Rap. With DJ Polo by his side, G dropped Road To The Riches on the world, and more or less started mob rap in doing so—in other words, a world away from what De La Soul was up to. It was also far away—geographically and artistically—from Houston's Geto Boys and their sophomore album, Grip It! On That Other Level—a raunchy, gleefully violent and amoral release that solidified the group's path into hip-hop history, sealing up what may be the weirdest trifecta of great rap albums ever released in the same month. —Foster Kamer

22. July 1998

Notable Events:
- Noreaga's N.O.R.E. is released on 7/14/1998
- Beastie Boys' Hello Nasty is released on 7/14/1998
- Lauryn Hill's "Doo Wop (That Thing)" is released on 7/27/1998

At the beginning of July 1998, the summer looked all but locked down for former Fugees member Pras, who had collaborated with Mya and Ol' Dirty Bastard on the monster "Ghetto Superstar" the month before. Little did they know, another Fugees member was on her way to a new stratosphere of hip-hop success. Lauryn Hill's debut single as a solo artist, "Doo Wop (That Thing)," quickly took over radio. Separate from any group affiliations (and from an entirely harder division of rap) was N.O.R.E., the debut album of Queens-bred talent Noreaga (although "Superthug" wouldn't hit radio for another two months).

But while July saw unheard talent emerging, and previously known talent chancing it solo, it also saw the simple thrill of old dogs doing new tricks: After four years without a new album, the Beastie Boys emerged with Hello Nasty, an album that remains what is arguably the group's most left-of-center output. It was part party album, part meditative navel-gaze record—and also a callback to their New York City roots and a love letter to the lost art of old-school MC-ing. Shit was weird, sure, and it wasn't for every party, either. But it came through when it mattered, which is to say: Of everything released that month, it sounded the best when played at deafening volume, and still does. -Foster Kamer

21. December 2002

Notable Events:
- Common's Electric Circus is released on 12/10/2002
- Nas' God's Son is released on 12/13/2002

The end of 2002 was a time for healing in America and in hip-hop. The wreckage of the Twin Towers was still smoldering. The Jay-Z vs. Nas feud was simmering down, but "Stillmatic" and "Got Yourself a Gun" were still getting spins on radio, while Jay-Z's "Takeover" was evolving past rap into a mogul movement. For Nas, it was an especially difficult time: His mother Anne Jones died of cancer earlier that year. No wonder, then, that his album God's Son is one of his most introspective and vulnerable, with tracks like "Dance," "Heaven," and "Thug's Mansion" musing on the afterlife and the loss of his mother. Rounded out with a trio of bangers—"Made You Look" "Get Down," and "Last Real Nigga Alive"—God's Son ranks near the top of Nasty Nas's discography because he was willing to take risks.

Three days earlier, another virtuoso MC dropped a risky album. Common's Electric Circus didn't fare as well, commercially or critically, as Nas' release, but it pushed past the boundaries of hip-hop to embrace rock, pop, soul, and electro sounds—anything but the same old, same old. Three years later, he would return to form with the Kanye West–produced classic Be, but first he had to get all this other stuff out of his system. Call it musical healing. -Rob Kenner

20. September 1993

Notable Events:
- De La Soul's Buhloone Mindstate is released on 9/21/1993
- Digable Planets' Reachin' (A New Refutation of Time and Space) is released on 9/27/1993
- Lords of the Underground's Here Come the Lords is released on 9/27/1993
- Souls of Mischief's 93 'til Infinity is released on 9/28/1993
- KRS-One's Return of the Boom Bap is released on 9/28/1993

Everybody knows about 1988, arguably the best year hip-hop has ever seen. But five years later, during the month of September, there was another, less celebrated explosion of creativity within the art form that yielded a dizzying variety of diverse musical experiments. Those who were alive and aware at the time remember the feeling. There was something in the air, and it felt like hip-hop could do anything. It was not yet all about the Benjamins, but instead about raw creativity, blending live instruments, jazz samples, and restlessly pushing lyricism to new heights. You could hear it on Souls of Mischief's debut, as the Bay Area bohemians married rigorous lyricism with rugged beats to assert a new Hieroglyphics aesthetic that would sustain them and comrades like Casual as an independent movement for decades to come.

Meanwhile, a young and hungry DJ Premier linked with super-MC KRS-One to craft a back-to-basics album whose cover featured KRS rhyming into a pair headphones. Native Tongue veterans De La Soul were building with James Brown hornsman Maceo Parker and rap phenomenon Biz Markie on Buhloone Mindstate, an album which they proudly declared "might blow up but it won't go pop."

Going pop was not a problem for Digable Planets, whose single "Rebirth of Slick (Cool Like Dat)" was inescapable—even stations that hated rap could not resist the trio's Fred Wesley horn sample and hepcat slang. Brooklyn's Lords of the Underground also dropped their debut that month, epitomizing the prevailing underground aesthetic. As raw and uncompromising as they wanted to be, they still managed to land five singles on the Billboard charts, of which "Chief Rocka" remains both a fan favorite and a mission statement: "I amaze and astound, rhythm up and down/Smack a group of them around, let them know who wears the crown." In September of 1993 nothing else mattered. -Rob Kenner

19. March 1997

Notable Events:
- Scarface's The Untouchable is released on 3/11/1997
- The Notorious B.I.G.'s Life After Death is released on 3/25/1997

It was the best of times, it was the worst of times. Hip-hop's tale of two cities—New York and Los Angeles—came to a tragic conclusion in the early morning hours of March 9, 1997, when Christopher Wallace aka The Notorious B.I.G. was gunned down while sitting in an SUV shortly after leaving a Soul Train Awards after-party hosted by Vibe magazine at L.A.'s Petersen Automotive Museum. Biggie's murder at age 25 came just six months after his friend turned rival Tupac Shakur was killed in another car-to-car drive-by shooting. In the blink of an eye, hip-hop's two biggest, brightest lights were snuffed out. Biggie's funeral procession on March 19 caused unruly cathartic celebration in the streets of Brooklyn as throngs came out to pay their last respects to the assassinated King of New York. Less than a week later his double album Life After Death was unleashed on a still shell-shocked hip-hop nation.

The record Biggie hoped would cement his reputation as the best rapper alive sounded totally different knowing the virtuoso rapper heard on tracks like "Kick In The Door" and "Going Back To Cali" and "Notorious Thugs" wasn't alive anymore. Clouded by grief, it was painful to hear all those songs that referred to his "so-called beef with you-know-who"—"What's Beef" and "Long Kiss Goodnight" and "You're Nobody Till Somebody Kills You" for God's sake—not to mention the cover art featuring Biggie standing in front of a hearse. It was all too much. And at the same time, it was not nearly enough. Sixteen years later the album stands as one of the greatest in rap history.

That same month, Texas O.G. Scarface released The Untouchable, which hit stores just two days after Biggie's murder, and reached No. 1 on the R&B/Hip-Hop Albums chart. The lead single was called "Smile" and it opened with a posthumous verse from Tupac Shakur. "It's gon' be some stuff you gon' see/That's gon' make it hard to smile in the future," 'Pac said at the top of the track. "But through whatever you see/Through all the rain and the pain/You gotta keep your sense of humor/You gotta be able to smile through all this bullshit/Remember that-Mmm, yeah/Keep ya head up." And somehow we did. -Rob Kenner

18. August 1998

Notable Events:
- Lauryn Hill's The Miseducation of Lauryn Hill is released on 8/25/1998
- Xzibit releases 40 Dayz and 40 Nightz on 8/25/98
- Black Star's Mos Def & Talib Kweli Are Black Star is released on 8/26/1998
- Sporty Thievz's "Cheapskate (You Ain't Gettin' Nada)" is released on 8/30/1998

Talk about getting the other side of the story: August '98 was a month of them, on both large and small scales. At the end of the month, a little-known group out of Yonkers became instantly famous for their someone-needed-to-say-it response to TLC's "No Scrubs" (still burning on charts at that point). And sure, it might be the thing they're most famous for, but Sporty Thievz's "No Pigeons" isn't a terrible thing to be known for: It was a funny, weird, and oddly therapeutic moment in rap. As far as larger-scale responses go, a little over a year after former Fugees member Wyclef Jean released his solo debut The Carnival, his ex-lover and bandmate Lauryn Hill's The Miseducation of Lauryn Hill bowed to rave reviews, blowing Wyclef, every other female rapper, and everyone else in rap away, with strong singles and videos. That isn't to say men only fixated on their female counterparts' efforts that month. "Conscious" rappers Mos Def and Talib Kweli bolstered both of their careers by teaming up for a left-of-center rap or superduo with the release of Black Star's Mos Def & Talib Kweli Are Black Star. Outside of the Tri-state area, Xzibit's sophomore effort 40 Dayz and 40 Nightz was a case of realized potential: Everyone who told everyone else that they were sleeping on the rapper finally had their vindication, as X peaked with "What U See Is What U Get," both on the charts and creatively, too. —Foster Kamer

17. May 2000

Notable Events:
- Eminem's The Marshall Mathers LP is released on 5/23/2000
- Deltron 3030's Deltron 3030 is released on 5/23/2000

May 2000 is a massive month in rap history for two reasons: Eminem'sThe Marshall Mathers LP and Deltron 3030. One was a major coup for mainstream hip-hop, the other was the same, for the underground. For an idea of just how insanely huge The Marshall Mathers LP's impact was, and why, really, its release alone is enough to place May 2000 as one of the genre's greatest months, consider this: The album sold 1.76 million copies in its first week. That's still the third best first-week tally in American history, and is only bested by 'N Sync's last two albums. Deltron 3030 was the debut from the supergroup of the same name comprised of Dan the Automator, Del the Funky Homosapien, and DJ Kid Koala. The album struck a chord with its conceptual presentation, relevant commentary on corporate power, and futuristic themes. All three members went on to work with Gorillaz, solidifying the appreciation of their contributions to music. —Ernest Baker

16. May 1998

Notable Events:
- DMX's "Ruff Ryders Anthem" is released on 5/5/1998
- Jermaine Dupri's "Money Ain't a Thang (feat. Jay-Z)" is released on 5/11/1998
- Beastie Boys' "Intergalactic" is released on 5/12/1998
- Bulworth is released in theatres on 5/15/1998
- DMX's It's Dark and Hell Is Hot is released on 5/19/1998

The incendiary emergence of DMX became very real in May of 1998, propelled by his seminal debut It's Dark and Hell is Hot. Speaking to a young and tenacious audience that was beaten but not buried, the Yonkers-bred MC's ravenous vocals snapped over gritty production, capturing a space in hip-hop that traded in Rolexes and shiny suits for a tattered bandana and a Louisville Slugger. His impetuous single "Ruff Ryders Anthem" perfectly personified this aesthetic, and when It's Dark entered the Billboard charts at No. 1 a week later, it was clear who the top dog was.

In stark contrast, a budding producer out of Atlanta was looking to shape his own rap career, but with money as his motivation. After scoring hits for singers and MCs alike, Jermaine Dupri snagged Brooklyn's finest for a record that proposed an affluent toast to the lavish life. Dupri may not have been lyrically up to snuff on "Money Ain't a Thang," but the song was an integral moment in expanding the regional barriers previously held in rap. —Edwin Ortiz

15. July 1996

Notable Events:
- Nas' It Was Written is released on 7/2/1996
- UGK's Ridin' Dirty is released on 7/29/1996
- A Tribe Called Quest's Beats, Rhymes and Life is released on 7/30/1996

July 1996 is probably best remembered for the release of Nas' It Was Written. Biggie, 2Pac, and Snoop changed the game in years prior by making creative albums that were also commercial smashes. This left Nas—who had plenty of props but no platinum plaque for Illmatic—in the tough position of not only following up a classic, but also in need of a commercial breakthrough. With "Street Dreams" holding down the streets, and "If I Ruled The World" holding down Billboard, Nas had the best-selling album of his career while reaffirming that it was becoming more and more possible for rappers to make both creative and commercially successful music.

Far South of the streets of New York, Texas-based rappers UGK dropped their first major label release Ridin' Dirty. It didn't sell exceptionally well, but over the years it became revered as a classic and remains the main reason why ego trip once declared UGK the most underrated rap act. And finally, A Tribe Called Quest's Beats, Rhymes and Life spelled the beginning of the end for the group that would ultimately break up two years later. If you consider Midnight Marauders as the last great Golden Era rap release, then Beats spelled the demise of the acts from that era, signaling that rap's future now lay in the hands of not just Nas and UGK, but 2Pac, Biggie, Jay-Z, and a whole new breed of MCs. —Insanul Ahmed

14. September 1991

Notable Events:
- Naughty By Nature's Naughty by Nature is released on 9/3/1991
- Nice & Smooth's Ain't a Damn Thing Changed is released on 9/3/1991
- W.C. and the Maad Circle Ain't a Damn Thing Changed is released on 9/17/1991
- A Tribe Called Quest's The Low End Theory is released on 9/21/1991

1991: The year the Soviet Union was disintegrating. That September, the United States recognized the independence of former republic states Estonia, Latvia, and Lithuania. Hip-hop, too, was continuing to break apart and evolve, as a string of sophomore records found the late-80's new school rookies evolving. New Jersey made its stamp on the industry as Naughty By Nature shot from obscurity. Recently renamed—the group first appeared as The New Style in 1989 for one unsuccessful LP—Treach, Vinnie, and Kay Gee had released lead single "O.P.P." only days earlier, and the song would soon rocket to No. 6 on the Billboard charts. After the self-titled album was released, it would only take until February 1992 to reach platinum sales off the surprise smash.

Meanwhile, Def Jam had begun to splinter, much like the once-mighty Baltic states. One of Rush Associated Labels' few successes, Nice & Smooth released their second LP, Ain't a Damn Thing Changed, and found a surprise minor hit with the Tracy Chapman-sampling "Sometimes I Rhyme Slow." In one of the strangest coincidences in rap history, West Coast rapper W.C. and his crew the Maad Circle (which included future star Coolio) would release a certified rap classic similarly titled Ain't a Damn Thang Changed—in this case, the group's debut. Apparently, no matter where you were, the streets were unchanged—even if hip-hop would never be the same.

Of course, one of the greatest sophomore records in rap history was also released in September 1991, when A Tribe Called Quest dropped their impeccable Low End Theory. A maturation of the group's playful debut, it maintained a lighthearted style, but found the trio's sound developing into a distinct aesthetic of its own, exploring new sampling sources and a fully developed chemistry between MC's Phife and Q-Tip. —David Drake

13. November 2010

Notable Events:
- Kid Cudi's Man on the Moon II: The Legend of Mr. Rager is released on 11/9/2010
- Nicki Minaj releases Pink Friday on 11/19/10
- Kanye West releases My Beautiful Dark Twisted Fantasy on 11/22/10

November 2010 saw landmark releases from three of hip-hop's finest of the past decade. First, Kid Cudi struck gold after 58 weeks on the charts for his debut album Man on the Moon: The End of Day with its follow-up, Man on the Moon II: The Legend of Mr. Rager. His sophomore effort was another look into Cudi's reality, with theatrical production and the brutally emotional and raw lyricism that drew fans in on his first album. The theatrics continued when Young Money's Queen hit the industry with Pink Friday, her quick claim to the female rap throne. With its first single, "Super Bass," Nicki ascended to the top of the charts with dazzling production, an array of voices and accents, and the ability to spit flames over synth-pop, heavy bass, and a range of love songs to explicitly braggadocios rhymes. Three days later, Nicki's faux-British-accent and an overwhelmingly alluring piano chord progression that crescendoed along with the lyrics, "Can we get much higher?" led into "Dark Fantasy," the first track on Kanye West's My Beautiful Dark Twisted Fantasy. An all-encompassing record, MBDTF represents Kanye's career strengths: the soul, the melodies, the symphonies, the dazzling production, electronic elements. It took fans, and West, to their greatest emotional extremes. —Lauren Nostro

12. October 1991

Notable Events:
- Scarface's Mr. Scarface is Back is released on 10/3/1991
- Public Enemy's Apocalypse 91...The Enemy Strikes Black is released on 10/3/1991
- Freestyle Fellowship's To Whom It May Concern... is released 10/5/1991
- The U.M.C.'s Fruits of Nature is released on 10/14/1991
- Black Sheep's A Wolf in Sheep's Clothing is released on 10/22/1991
- Del the Funky Homosapien's I Wish My Brother George Was Here is released on 10/22/1991
- Organized Konfusion's Organized Konfusion is released on 10/29/1991
- Ice Cube's Death Certificate is released on 10/29/1991

October '91 wasn't as groundbreaking as some other months in rap history; there weren't any releases that completely shifted the playing field like July 1997 or April 1994. But when grumpy old rap heads talk about the Golden Era, and how much damn fun it was to be a rap fan in the early '90s, this is one of the months they're referring to.

Let's say you turn 15 in October 1991. You've got a part, part-time job washing dishes for $4.25/hour (that was the minimum wage in '91 *cue the world's smallest violin*). You're taking home about $60 a week. What to spend it on? Well, you've got to pick up Public Enemy's new album, they're the biggest rap group in the world (you'll be a little disappointed, although the beat for "By the Time I Get to Arizona" will always give you chills). If you know what's up, you'll nab Scarface's debut on the very same day (you won't be disappointed at all). Three weeks later, you're back at the record store to cop a couple more debuts, A Wolf in Sheep's Clothing (because of the Native Tongues co-sign) and I Wish My Brother George Was Here (because of the Ice Cube co-sign). And then one week later you're back to get Ice Cube's Death Certificate (be honest: you didn't even no what the phrase "No Vaseline" meant back then) and Organized Konfusion (be honest: you're lying through your fucking teeth if you tell us that you were 15 and bought OK the day it dropped, but that's cool, rap is used to a little embellishment).

For those of you scoring at home, that's three certified classics (Mr. Scarface, Death Certificate, Organized Konfusion), one near-classic (A Wolf in Sheep's Clothing), a cool oddity (I Wish My Brother George Was Here), and a good (but not great) effort from the world's most important group (Apocalypse 91...The Enemy Strikes Black). Sure, you've spent all your hard-earned dishwashing loot, but with that musical haul, who needs to leave the house anyway? —Jack Erwin

11. August 1990

Notable Events:
- Kool G Rap & DJ Polo's Wanted: Dead or Alive is released on 8/13/1990
- N.W.A.'s 100 Miles and Runnin' is released on 8/14/1990
- Too Short's Short Dog's in the House is released on 8/27/1990
- LL Cool J's Mama Said Knock You Out is released on 8/27/1990
- Vanilla Ice's To the Extreme is released on 8/28/1990

In August of 1990 hip-hop was going through a transition. A couple vets solidified their legacies, an established star reached maturation, and a newcomer threatened the art form's very foundations. But first, the West Coast certified that the first shots fired a few years earlier by groundbreaking groups N.W.A. (Straight Outta Compton) and Too $hort (Born to Mack and Life is...Too Short) were no flukes. Although Too $hort's Short Dog's in the House wasn't quite as big as its preceding record, the album went platinum, the second in a string of six platinum LPs for the rapper. N.W.A.'s 100 Miles and Runnin EP faced more of a challenge: How would the group survive without recently departed member and primary lyricist Ice Cube? As it turned out, they would flourish; the EP was a success, paved the way for the following year's Efil4zaggin, and signaled the further development of Dr. Dre's production style. The EP's title track would be the producer's last major uptempo track.

On the East Coast, LL Cool J became one of the genre's longest-running success stories when his LP Mama Said Knock You Out revitalized his career after the disappointment that was 1989's Walking With a Panther. The record, produced almost entirely by Marley Marl, was a critical and commercial success, ringing in double-platinum sales. Marl's Juice Crew member Kool G Rap released Wanted: Dead or Alive alongside DJ Polo in August as well. It was the duo's second full LP, and it solidified G Rap's reputation as one of the best hardcore rappers in New York, his street stories an unvarnished look at the city's violence with a cinematogropher's eye. At the end of the month, of course, came the jolt that would shock the hip-hop world, as Vanilla Ice's massive To the Extreme suggested that for all its sonic diversity, hip-hop's future might be whitewashed before the genre even had a chance to make much of a creative impact. These fears turned out to be unfounded, of course. But at the time there was real cause for alarm. The record would spend 16 weeks at the top of the charts and ship seven million copies. —David Drake

10. September 2007

Notable Events:
- Kanye West's Graduation is released on 9/11/2007
- 50 Cent's Curtis is released on 9/11/2007
- Flo Rida f/ T-Pain's "Low" is released on 9/16/2007

September 2007 marked the beginning of one of the more cringe-worthy eras of pop rap when Flo Rida and T-Pain's "Low" became the starter pistol of what seemed like a million other auto-tuned and pop-driven "hits" while delivering the genre of Bar Mitzvah-rap another seminal entry. But it was also the month when Kanye West and 50 Cent's public "beef" came to a head. Both rappers scheduled their crucial third album releases for the same day, and Fitty put his career on the line (but not really) when he told SOHH that if Kanye moved more copies of Graduation than he sold copies of Curtis, he would "no longer [perform] music." Of course, Kanye outperformed 50; 50 blamed his troubles on bad marketing. For a month, hip-hop fans didn't just get two albums by two crucial artists, they got something a little less tangible: The ability to take sides in a non-violent beef and watch the results play out in real time. Since then, Kanye's dropped three categorically hot albums. Fif's dropped one, and it didn't blow up. As the saying goes: Vox populi, vox hip-hopuli. —Foster Kamer

9. September 2001

Notable Events:
- J.Lo's "I'm Real (feat. Ja Rule)" is released on 9/4/2001
- Jay-Z's The Blueprint is released on 9/11/2001
- Fabolous' Ghetto Fabolous is released on 9/11/2001
- Aesop Rock's Labor Days is released on 9/18/2001 - N.E.R.D.'s In Search of... is released on 9/28/2001

Yes, the month of what's possibly the most infamous tragedy in American history is also indisputably one of the greatest months in hip-hop history. First and foremost, Jay-Z released what many consider to be his best album, The Blueprint—on September 11, no less. The same day, Fabolous released his debut, Ghetto Fabolous, which also found notable success, despite its correlation with the terrorist attacks and competition from Hov. Ja Rule was also in the midst of a dominating run, and his pop smash with Jennifer Lopez, "I'm Real," was No. 1 on the Hot 100 for most of the month. The Neptunes, who were no stranger to mainstream success by September 2001, broadened their horizons with the release of their N.E.R.D debut, In Search Of... But it wasn't just a month for the mainstream: It was also a landmark for underground hip-hop, with Aesop Rock releasing his first Definitive Jux record, Labor Days. —Ernest Baker

8. February 1999

Notable Events:
- Eminem's The Slim Shady LP is released on 2/23/1999
- The Roots' Things Fall Apart is released on 2/23/1999
- Lauryn Hill wins 5 Grammys for The Miseducation of Lauryn Hill on 2/24/1999
- Jay-Z's Vol. 2... Hard Knock Life wins the Grammy Award for Best Rap Album on 2/24/1999 and boycotts show

In February 1999, the Grammy committee finally shrugged off a longtime trend of awarding their highest plaudits to (typically) white men by delivering Lauryn Hill ten nominations and five Grammys for The Miseducation of Lauryn Hill, including Album of the Year. Meanwhile, Jay-Z's Vol 2...Hard Knock Life won Best Rap Album, but Hov wasn't there to accept it, because Jay-Z boycotted the Grammys for not respecting rap.

That same week also saw the release of two equally crucial but diametrically opposed albums that would leave their own marks in hip-hop: The Roots's Things Fall Apart and Eminem's debut album, The Slim Shady LP. While Black Thought, ?uestlove, and the rest of The Roots would go on to change the definition of what it means to be a critical darling of rap (and what that doesn't mean for success), Eminem's reputation of being equal measures widly popular and widely reviled would redefine the legacy of white rappers, Dr. Dre, Detroit's rap legacy, and rap's place in popular culture (among other things). In other words, it was a month of All Hallmarks Everything, and one not coincidentally marked by an open rebellion of norms, too. -Foster Kamer

7. November 1996

Notable Events:
- Makaveli's The Don Killuminati: The 7 Day Theory is released on 11/5/1996
- Snoop Dogg Tha Doggfather is released on 11/12/1996
- Lil' Kim's Hard Core is released on 11/12/1996
- Foxy Brown's Ill Na Na is released on 11/19/1996
- DJ Shadow's Endtroducing..... is released on 11/19/1996
- Mobb Deep's Hell on Earth is released 11/19/1996
- Keith Murray's Enigma is released on 11/26/1996

Hip-hop was still grieving in November of '96 from the death of 2Pac less than two months earlier in Las Vegas. His tracks from All Eyez On Me—particularly "I Ain't Mad at Cha," released as a single two days after his death—were still in heavy rotation when singles from his second album of the year, The Don Killuminati: The 7 Day Theory began to appear. Those singles, "Toss It Up" and "To Live & Die in L.A.," were released in September, and flooded the airwaves by the time the full album dropped in November. 'Pac's record, released under the pseudonym Makaveli, debuted at No. 1 on the charts, and set the highest selling first-week sales record for that year. By the end of the decade it would be certified four times platinum.

Meanwhile, one of the groups 'Pac was beefing with around this time released their own LP only two weeks later; Mobb Deep's Hell on Earth was a paranoid, claustrophobic, and frighteningly kinetic follow-up to the group's classic The Infamous. Pac's primary musical nemesis, Biggie, had yet to release the lead single from his Life After Death LP. However, a former protege and associate of Big's named Lil Kim released her debut LP that month to strong sales. The raunchy Hard Core was the highest debuting rap album by a female artist to that point.

She wasn't the only female MC making strides in the marketplace. Foxy Brown's Ill Na Na also dropped in November '96, a celebration of The Trackmasters' clean, '80s R&B-sampling production sound. Its second single, the Rene and Angela-swiping "I'll Be," struck Billboard's top ten, becoming the biggest hit to that point for both Foxy and featured artist Jay-Z. Although sophomore records by both Snoop Dogg and Keith Murray failed to find the same commercial footing as their debuts, each has some underrated moments. Meanwhile, DJ Shadow released the instrumental hip-hop record Endtroducing...., which transformed hip-hop into particularly evocative mood music, and quickly became your favorite record store clerk's favorite hip-hop record, and one of your favorite producer's most essential. —David Drake

6. April 1994

Notable Events:
- Nas' Illmatic is released on 4/19/94
- OutKast's Southernplayalisticadillacmusik is released on 4/26/94

It's not like Nasty Nas and OutKast snuck up on anyone in April 1994. Nas's buzz had been building for three years, ever since he announced himself as the "street's disciple" on Main Source's "Live at the Barbecue." Big Boi and Andre 3000 were on everyone's radar already, too; "Player's Ball" had been released the previous Christmas, heralding a new, crisp sound coming from the South. But put it like this: On Monday, April 18, rap was one way. Nine days later—after the release of the debut albums by artists who would completely alter the landscape of hip-hop—it was something else entirely.

Looking back, the albums are oddly similar, down to the intro-segueing-into-gradually-building first track openings. What they would portend were two different things entirely though. For much of the 19 years since SPCM's release, Atlanta has been the epicenter of hip-hop, and that's directly traceable to OutKast's debut. And Illmatic is, well, Illmatic. There's Before Illmatic and Southernplayalisticadillacmuzik, and After Illmatic and Southernplayalisticadillacmuzik. It's that simple. —Jack Erwin

5. July 1997

Notable Events:
- Puff Daddy & the Family's No Way Out is released on 7/1/1997
- Missy Elliott's Supa Dupa Fly is released on 7/15/1997
- Company Flow's Funcrusher Plus is released on 7/28/1997
- Bone Thugs-N-Harmony's The Art of War is released on 7/27/1997

July of 1997 was a month of narratives ending and beginning, closing and opening.

Mike Tyson was suspended from boxing for biting Holyfield's ear; Howard Stern had been fired from his Dallas radio station gig, starting his rise as talk radio's shock jock king. Rap was still reeling from the death of The Notorious B.I.G. four months earlier; Puff Daddy & the Family's No Way Out continued the grieving process. Haunted by the specter of Biggie on tracks like "Victory" and "All About The Benjamins," Puff and Bad Boy owned the summer in the wake of their loss. But while Diddy prospered in mourning and epitomizing the hip-hop conventions of the day, Missy Elliott's Supa Dupa Fly picked up on the tidal shift of Southern rap left off by OutKast's ATLiens. Elsewhere, Midwestern all-stars Bone Thugs-N-Harmony's The Art of War continued the group's reign of R&B/gangsta rap crossover with lead singles "If I Could Teach The World" and "Look Into My Eyes" (assisted by an appearance on the star-studded soundtrack for Batman & Robin). Off the charts, a long ways away from rap radio but right around the corner from Bad Boy back in Brooklyn, every cliché about rappers "starting a movement" was being put to shame as Company Flow dropped their debut, Funcrusher Plus, which also happened to be the first release of a burgeoning independent label called Rawkus Records. —Foster Kamer

4. February 1996

Notable Events:
- 2Pac's All Eyez on Me is released on 2/13/1996
- The Fugees' The Score is released on 2/13/1996
- Snoop Dogg is acquitted of murder charges on 2/20/1996
- Naughty by Nature's Poverty's Paradise wins the Grammy Award for Best Rap Album on 2/28/1996

It was a month for history: 2Pac released the first major-release double album in rap music, All Eyez on Me. The rush-recorded set debuted at No. 1 on the Billboard pop charts and solidified 'Pac's status as one of the biggest figures in pop culture, much less rap. Eyez eventually went nine times platinum and became Tupac's best-selling album. Of course it was the last album he released in his lifetime; it was also one of the last great albums of the West Coast's mid-'90s heyday.

The same day Eyez dropped, The Fugees released their second and final album The Score, an effort as different from 'Pac's as could be. The Score peaked at No. 1 on the charts as well. and has since been certified platinum six times over. The success of the album, in particular, the single "Killing Me Softly" released a month later, would propel Lauryn Hill to a superstardom that, like 'Pac's, would transcend rap and dominate pop culture as well. —Lauren Nostro

2. August 1988

Notable Events:
- Salt-n-Pepa's A Salt With A Deadly Pepa is released on 8/2/1988
- Yo! MTV Raps debuts on 8/6/1988
- NWA's Straight Outta Compton is released on 8/8/1988
- EPMD's Strictly Business is released on 8/20/1988

August '88 would've been notable for Deadly Pepa and Strictly Business alone, the sophomore and debut albums from two of rap's most beloved groups. But this was the month that ruined many a parent's life in the 1990s (and beyond) for other reasons. The funny part is, the poor saps didn't even know it at the time.

On Saturday, August 6, 1988, MTV debuted a program whose pilot became one of the most watched shows in the channel's history at that point: Yo! MTV Raps. That first episode was hosted by Run-DMC; DJ Jazzy Jeff and the Fresh Prince appeared as well. The first video aired was Eric B. & Rakim's "Follow the Leader." With the rappity rap now broadcast into the homes of millions of teenagers, America (and the world) would never be the same.

Run-DMC and Eric B. & Rakim were enough to strike fear in the hearts of parents in middle America (Jazzy Jeff and the Fresh Prince probably struck fear in the hearts of parents in middle America back then), but two days later, a group that should've really scared the shit out of parents the world over released their debut album. There hadn't been anything like N.W.A. in music up to that point-at least not on the level they eventually reached. Rap had violent, misogynistic lyrics before N.W.A., they just weren't spit so gleefully. Yo! MTV Raps didn't play N.W.A. that much (how could they?). It didn't matter. Once the show hit the airwaves, it was just a matter of moving a few rows over in the "Rap" section of the record store before kids found Straight Outta Compton while looking for "Parents Just Don't Understand." At which point it was game over for said parents. -Jack Erwin

2. September 1998

Notable Events:
- Jay-Z's "Can I Get A... (feat. Amil and Ja Rule)" is released on 9/1/1998
- Canibus' Can-I-Bus is released on 9/8/1998
- Noreaga's "Superthug" is released on 9/21/1998
- OutKast's Aquemini is released on 9/29/1998
- Jay-Z's Vol. 2... Hard Knock Life is released on 9/29/1998
- A Tribe Called Quest's The Love Movement is released on 9/29/1998
- Brand Nubian's Foundation is released on 9/29/1998
- Eminem's "Just Don't Give A Fuck" music video drops

September 1998 was a month for the beginning of legacies. The world was just starting to realize the potential of the Internet when two already well-accomplished PhDs named Sergey Brin and Larry Page planted the humble roots of their little online startup, Google. Who would've known it would turn out to be the behemoth it is today? They weren't the only ones.

Take for example OutKast's third album, Aquemini which The Source deemed worthy of their (once-coveted) Five Mic review. It wasn't just a hit in its own right, it affirmed the M.O. of OutKast—to zig when everyone else zagged—that would produce an even further-left-of-center album in Stankonia two years later. As for those zags? Jay-Z dropped his seminal Vol. 2... Hard Knock Life, flipping hooks out of everything from Annie to Swizz Beats dragging his hand across a keyboard. Speaking of production: Noreaga's "Superthug" dropped, sure, but it was that crazy beat by those Neptunes kids that seemed to catch everyone's attention. LL Cool J beef-famous rapper Canibus would drop his highly anticipated eponymous debut album, but years later—when people are still thirsting for another OutKast album, and when Jay-Z became the owner of more than just a three-volume music franchise—he's still remembered mostly for that beef. If you don't quite remember it, well, please, let us Google that for you. And of course, for A Tribe Called Quest, it was the end, as they dropped their final album, The Love Movement. —Foster Kamer

1. November 1993

Notable Events:
- Wu-Tang Clan's Enter The Wu-Tang (36 Chambers) is released on 11/9/1993
- Snoop Dogg's Doggystyle is released on 11/23/1993
- Del the Funky Homosapien's No Need for Alarm is released on 11/23/1993
- A Tribe Called Quest's Midnight Marauders is released on 11/9/1993
- E-40's Federal is released 11/10/1993

If you wanted to give an alien a crash course in the diversity of rap in the '90s, you could do worse than playing him only albums released in November 1993. You've got three certified classics, in three genres: Tribe's Midnight Marauders and Wu-Tang's 36 Chambers, released on the same day (here's a New York rap Rorschach test: you've got $15 that Tuesday, which album do you buy?), and Snoop's Doggystyle, which dropped two weeks later. Throw in a couple cult hits from the Bay, E-40's debut and Del's slept-on sophomore gem, and your extraterrestrial pal will have a pretty good idea of what hip-hop was like at the end of its Golden Era.

For the rap historian though, November '93 is fascinating beyond just the albums that dropped that month. Looking back, you can see the tectonic hip-hop plates shifting. The month belonged to Snoop, of course. Doggystyle debuted at No. 1 on the Billboard charts and sold 800,000 copies its first week, then a record for a debut artist. Just 22, Snoop had already appeared on the cover of Rolling Stone, and West Coast gangsta rap was ascendant.

Back East, Tribe and Wu dropped on the same day, but the groups—and the styles they repped—were headed in different directions. Midnight Marauders was Quest's fastest selling album, but it was also their last great one. The group began to drift apart afterward, and the Tribe vibe they defined—scholarly but fun, hard-hitting sans the overt violent imagery—would soon be surpassed by the rise of gangsta culture on both coasts. Wu-Tang played a pivotal role in ushering in that shift. Their emergence signalled the return of East Coast hardcore rap, paving the way for Nas and Biggie after them, but also pushing Tribe and their contemporaries to the margins. —Jack Erwin