1996: 2PAC

CREDENTIALS: All Eyez on Me, The Don Killuminati: The 7 Day Theory, drops epic diss track “Hit ‘Em Up”

2Pac’s tireless work ethic and prolific output made him a legend, and 1996 saw both of those habits at their highest efficiency. For most of the previous year, he was incarcerated, after being found guilty on three counts of molestation. 2Pac was released from Clinton Correctional Facility in October 1995, Suge Knight successfully recruited him to Knight’s infamous, powerful record label, Death Row, and the rapper launched into the next year with unprecedented resilience.

2Pac’s historical tear through 1996 began with the release of All Eyez on Me in February. By then, he had become a mainstream fixture—an icon larger than rap—and it was evident in the album’s reception. It debuted at No. 1 on the pop charts and moved 566,000 units in its opening week, achieving 5X platinum certification by April. But 2Pac’s appeal that year goes much deeper than sales statistics.

Commercial and creative peaks don’t always correspond, but they did for 2Pac. When his Top 40 presence reached its pinnacle, so did his rapping. Consider the urgent tenacity that embellishes All Eyez on Me’s opening lines: “So many battlefield scars while driven in plush cars/This life as a rap star is nothing without heart.” For the first time, 2Pac brought all of the lyrical dexterity of his East Coast peers, without sacrificing the emotional delivery for which he’d become known. He was a master of what he said and how he said it.

The masses recognized this, and that summer, the singles “How Do U Want It” and “California Love” reached No. 1 on the Billboard Hot 100. They were the first rap songs not bathed in pop-slanting crossover tactics to hold claim to such a feat, and proved that, for this very specific moment in time, Tupac Shakur was absolutely unstoppable, in every field. You could finally say that 2Pac’s potential was fully realized. His voice resonated with the public as much as it did with those on the block, a fact of which he was fully aware: “My lyrics motivate the planet/It’s similar to Rhythm Nation, but thugged out, forgive me Janet.”

This run appeared as if it might end when 2Pac was shot on Sept. 7, 1996, but he continued to rule the year, even from the grave. Don Killuminati: The 7 Day Theory, released two months after his death, was more successful upon its release than any of 2Pac’s preceding albums, selling 664,000 in its first week. He wasn’t floating on meticulous instrumentals with Redman and Method Man on this album, either.

2Pac’s work as Makaveli was more about bombast and calculated rhetoric. That approach gave way to some of the sharpest rhymes of his career. “Bomb First (My Second Reply)” and “Hail Mary” played like battle cries. Rhymes like, “I take this war shit deeply/Done seen to many real playas fall to let you bitch niggas beat me,” channeled his anger into commodity, with an artful consistency.

1996 is a case study for every aspect of why 2Pac is so celebrated. He was a viable, competent artist in multiple arenas, and he had the discipline to incorporate his varied and conflicted missions into a single mantra. That savvy paid off in this year more than any other. It’s a shame that 2Pac’s ride had to end early, and on someone else’s terms, but the dedication to his craft that was on such full display in 1996 is why he’ll live forever.

HONORABLE MENTIONS: The Notorious B.I.G., Nas, Jay Z
After what was, at that point, the best year of his career, Biggie remained a formidable competitor in 1996. He didn’t have much to offer in the way of new solo material, but his flawless streak of guest appearances was awe-inspiring. His verses on works like 112’s “Only You” remix and Lil’ Kim’s Hard Core kept him in the conversation.

New to that conversation was then-rookie Jay Z, whom Biggie had also given a feature for his fellow Brooklyn MC’s classic debut, Reasonable Doubt. It took some time for appreciation of the album to set in, but looking back, it’s clearly a remarkable project. The same can be said for Jay Z’s eventual foe, Nas, who released his sophomore album, It Was Written, the same year.

While the album was more commercially successful than Illmatic, it was met with a tepid response from hip-hop fans looking for a rehash of Nasir’s debut. But it was only a total disappointment to the hypercritical. Jay Z rapped, “Who’s the best MC—Biggie, Jay Z, or Nas?” the following year for a reason. —Ernest Baker


CREDENTIALS: Life After Death, back to back No. 1 hits with “Hypnotize” and “Mo Money Mo Problems,” guest spots on “Been Around the World,” “It’s All About the Benjamins,” and “Victory”

Christopher Wallace was only alive for 67 days in 1997, but with a talent so immense, that’s all it took for him to be the most dominant rapper of the year. In the months after Biggie’s March 9 death, it’s almost as if his stock rose. The untimely loss of someone so young, with so much heft in the language of hip-hop, was like a call to reflection. Infatuation with his wit, wordplay, and delivery soared, and 1997, in spite of tragedy, was Biggie’s biggest year.

Life After Death was released just over two weeks after Biggie passed and peaked at No. 1 on the Billboard 200. The album was an ambitious two-disc set with a tracklist comprised of every type of song imaginable. While the diverse styles and subject matter—his daughter’s college plan, kinky sex, hotel heists, a fully-sung ballad—were an organic product of Biggie’s incomparable range, the strategy of Life After Death’s sequencing has become the de facto approach for rap albums in the years since. It’s an incredibly influential project, before you even press play.

When Life After Death does start spinning, the true brilliance of Biggie’s persona and way with words comes into frame. The man was an expert at rapping, and he could wow from any angle. “Somebody’s Gotta Die” was a storytelling track with the complexities of an Alfred Hitchcock movie. “Notorious Thugs” had Biggie rhyming in a then-shocking double-time flow and besting Bone Thugs-n-Harmony at their own game. “Ten Crack Commandments” saw him detailing the rules of drug dealing in a manner so languid that you forget it’s a song and not a conversation. Mentioning three tracks doesn’t feel sufficient; literally every single record on Life After Death brings a different skill set of Biggie’s to the forefront.

It’s that aptitude and reach that keeps the Notorious B.I.G. in Greatest of All Time conversations, even with his limited amount of material. He dropped intricately arranged rhymes like, “Got the new Hummer in the summer when/I was a new comer then/Drugs and Mac-10s/Hugs from fake friends/Make ends, they hate you/Be broke, girls won’t date you,” with an alarming composure. All of Biggie’s lyrics were presented in an unorthodox pattern that nonchalantly challenged the conventions of rap delivery with every line.

Though Biggie’s songwriting and performance on those songs was at its most admirable in 1997, his untimely death sparked a wave of massive posthumous wins for the rest of the year, with singles “Hypnotize” and “Mo Money Mo Problems” both reaching No. 1 on the Hot 100.

The success of his mentor Puff Daddy’s solo venture, No Way Out, also kept Biggie in the spotlight, thanks to his star turns on “Victory” and the “It’s All About the Benjamins” remix. The way he takes the reins on both of those tracks, molding the instrumental to accommodate his prowess, commands a level of respect that’s difficult to dole out to less-deserving MCs in his wake.

Biggie was the most unavoidable voice in hip-hop that year, and for good reason. Every verse of his came equipped with a unique sense of charm, and proficiency, that couldn’t be found anywhere else. Biggie was the most entertaining rapper to listen to in 1997, from an everyman standpoint—think about how fun it is to spell out B-I-G-P-O-P-P-A at the beginning of his verse on “Mo Money Mo Problems”—and he was also the best, from a purist’s perch. That’s a rare circumstance, but Biggie was never ordinary.

HONORABLE MENTIONS: Busta Rhymes, Jay Z, Twista
While there’s no question that, even in death, Biggie owned 1997, his passing did open the door for other hip-hop acts to emerge. Busta Rhymes had been patiently waiting to make it since his “Scenario” verse five years prior, and the success of “Woo Hah!! Got You All in Check” in 1996 set him up nicely for the career explosion that occurred in 1997. Busta’s style remained avant garde, but his increased sense of speed and control—peep how he holds the same rhyme through every verse on “Put Your Hands Where My Eyes Could See”—earned him points on the technical end. Twista was another MC with a knack for lightning fast flows, and the fact the Adrenaline Rush rapper hailed from a city other than NYC made his leap to national consciousness even more notable.

Jay Z’s Das EFX-like doubletime days were behind him by 1997, but with his friend and collaborator Biggie gone, Hov’s talents became more noticeable. Not many people would take 1997’s In My Lifetime, Vol. 1 over the previous year’s Reasonable Doubt, but most will acknowledge that tracks like “Where I’m From” and “A Million and One Questions” are home to some of the best rhymes of Jay’s career. For Hov, it was the beginning of an unprecedented reign. —Ernest Baker

1998: DMX

CREDENTIALS: It’s Dark and Hell Is Hot, Flesh of My Flesh, Blood of My Blood, guest spots on “Money, Cash, Hoes” and “Money, Power, Respect”

As history tells it, Kurt Cobain and Nirvana saved rock from the death grips of hair metal in the early ’90s. After the glitz and glamour of hip-hop’s shiny suit Jiggy era, the emergence of Yonkers badass DMX was celebrated in the same way.

His debut single, “Get at Me Dog,” had no overwrought ’​80s pop sample, and its accompanying visual was a gritty black-and-white account of a night at legendary hip-hop nightclub the Tunnel, rather than an ostentatious display of wealth. The rap community welcomed this long-missed hardcore approach to the music with open arms, but DMX was more than a contrarian alternative to the popular hip-hop of time. He was, in his own right, an excellent rapper.

In subverting the mainstream, DMX became the mainstream. It’s Dark and Hell Is Hot debuted at No. 1 on the Billboard 200 and achieved multi-platinum sales. Timing plays a role in this success, but really, so much credit is owed to the fact that DMX was rapping with a truly original, at times jarring, audaciousness. His style was rooted in the wizardry of East Coast lyricism, but tracks like “Ruff Ryders’ Anthem” branched beyond that foundation, also incorporating a no-nonsense precision that had been relegated to acts from other regions—Juvenile, Trick Daddy—who were gaining attention at the time.

DMX made history in December 1998 when he released his sophomore album, Flesh of My Flesh, Blood of My Blood, and it too debuted at No. 1, making DMX one of the few artists in any genre to drop two chart-dropping LPs in one year. “Slippin” was the album’s only single, and though it didn’t perform well commercially, the album still went triple platinum.

By then, DMX’s triumphs weren’t a surprise. He was a movie star (Hype Williams’ feature-length debut, Belly, released in 1998), but his way of rhyming made everyone feel like a close friend. His energy, honesty, and vulnerability—“Didn’t keep a haircut or give a fuck how I dressed”—looped America into his narrative, and X has been impossible to ignore ever since. Jay Z won the Best Rap Album Grammy the following year and boycotted the ceremony because DMX wasn’t nominated. What does that tell you?

HONORABLE MENTIONS: Jay Z, Big Pun, Lauryn Hill
DMX’s record-setting run places him at the front of the pack, but 1998 saw several other hip-hop artists soar to equally dizzying heights as well. It was the year that Jay Z became a pop star, selling five million copies of Vol. 2… Hard Knock Life on the back of his massive Annie-sampling title track single. It was the year that Lauryn Hill stepped out as a solo force, selling eight million copies of The Miseducation of Lauryn Hill, the album that earned her a historical five Grammys in early 1999. It was the year that Big Pun finally saw the potential of his buzz fulfilled and dropped his critically acclaimed platinum debut, Capital Punishment. The accolades and mind-numbing sales figures of each artist were well-deserved, with Jay, Lauryn, and Pun all serving as model examples of the benefits an artist can reap as a result of settling in an uncompromising creative zone. —Ernest Baker

1999: JAY Z

CREDENTIALS: 1998’s Vol. 2… Hard Knock Life, Vol. 3…Life and Times of S. Carter, guest spots on “Heartbreaker” and “Lobster & Scrimp”

After the banner year that was 1998, Jay Z entered 1999 with his confidence at an all-time high. One lyric sums up his thoughts on the competition: “You got a little flow, that’s cool with me…but none of y’all motherfuckers can fool with me.”

Hov spent the majority of the year riding off the success of Vol. 2… Hard Knock Life, releasing singles “Money Cash Hoes” and “Nigga What, Nigga Who” from that album. For anyone who (somehow) missed out on Jay’s efforts the previous year, both tracks served as excellent confirmation of Jay’s rapid ascent. “Money Cash Hoes” had him effortlessly bending syllables over one of Swizz Beatz’s most unorthodox beats. “Nigga What, Nigga Who” saw Hov flowing faster than usual, without ever missing a step or compromising his depth.

That summer, he contributed “Jigga My Nigga” to Ruff Ryders compilation Ryde or Die Vol. 1. The best way to describe it in a word? Insane. The same goes for his guest verse on Mariah Carey’s No. 1 hit, “Heartbreaker.” Even on a straightforward feature about his dalliances with multiple women, the presentation was beyond sharp. His presence was like an insurance policy for any record.

This carried over to the first single for Jay Z’s next album, Vol. 3… Life and Times of S. Carter. “Do It Again (Put Ya Hands Up)” was a brash declaration, with statements that added up to: “I’m still here and I’m still better than you.” His performance on the record supported this, with a liquid delivery that mirrored the progression of the beat. Hov warned his doubters, “Don’t talk to me ’bout MCs got skills.” There was no need to after a year of such vast lyrical accomplishments.

DMX was still on a tear through the industry, and he captivated mainstream audiences and hip-hop heads alike with his five-times platinum …And Then There Was X. Eminem made his debut, simultaneously scaring and charming America with his immensely skilled shock raps. Nas dropped two albums in one year. Both were met with mixed reviews but, in retrospect, were still plenty heavy on the deft lyricism on which he based his reputation. Hov may have been in a lane of his own during 1999, but the market was more than competitive. —Ernest Baker

2000: EMINEM

CREDENTIALS: The Marshall Mathers LP, guest spots on “Forgot About Dre” and “Don’t Approach Me,” three classic singles with “Real Slim Shady,” “The Way I Am,” and “Stan,” becomes most controversial rapper on the planet.

After the immense success of The Slim Shady LP and Dr. Dre’s 2001, Eminem was riding high even as he became overwhelmed by the reach of his new found fame. Rather than crack under the pressure, Marshall took some time (and drugs) in Amsterdam, came back Stateside, and released his magnum opus, The Marshall Mathers LP. Even if it hadn’t become one of the best-selling rap records ever, the record was still a conceptual masterpiece—with Eminem mixing autobiographical detail and absurdist fantasy to chilling results.

As Em stepped into his prime, he began demolishing verses with an unparalleled tenacity for wordplay: “Sick sick dreams of picnic scenes/Two kids, 16 with M-16’s and 10 clips each/And them shits reach through six kids each/And Slim gets blamed in Bill Clint’s speech to fix these streets?” The detail was vivid and visceral. “And if it’s not a rapper that I make it as/I’ma be a fucking rapist in a Jason mask!” His music hit a nerve on critical, commercial, and cultural levels, aided by his blonde hair and blue eyes (as he’d soon point out), but an undeniable achievement nonetheless.

Singles like “Way I Am” showed Eminem for what he was. An angry white male? Sure. But also the only rapper who could score a massive pop hit by following the words of The 18th Letter. By 2000, white boy or no white boy, you had to give him the mic and let him recite.

HONORABLE MENTIONS: Jay Z, André 3000, Ghostface Killah
Jigga may not have released the best albums of his career at the turn of the century (Vol. 3 dropped the closing days of 1999 and The Dynasty dropped 10 months later), but he was fresh off skating to four-times platinum, and he did drop two of his biggest singles ever, “Big Pimpin'” and “I Just Want to Love You (Give It to Me).” His confidence had skyrocketed, and he was looking to assert himself: “Y’all niggaz ain’t rapping the same/Fuck the flow y’all jacking our slang/I seen the same shit happen to Kane/Three cuts in your eyebrow trying to wild out/The game is ours will never foul out/Y’all just better hope we gracefully bow out.” This was the last time Jay really had one foot in the streets (his infamous incident with Lance “Un” Rivera at the Kit Kat Klub took place in December 1999), so threats like, “No kids but trust me I know how to raise a gun,” packed more punch.

Meanwhile, after dropping consecutive platinum classics, OutKast’s André 3000 finally enjoyed being one of the Best Rappers Alive. He earned the distinction past his prime, but Andre’s shine had previously been overshadowed by massive forces like Biggie and 2Pac—the real culprits behind why OutKast got booed at the 1995 Source Awards. After already selling millions, OutKast gained wider recognition with the release of Stankonia and massive singles like “B.O.B.” and the group’s first No. 1 hit, “Ms. Jackson.” Finally, as Andre assured we would, we listened to what the South had to say.

Back up north in Shaolin territory, Ghostface Killah scored a victory for the floundering Wu-Tang empire with the release of his classic sophomore album, Supreme Clientele. The album was critically heralded though not commercially successful enough to get Ghost wider recognition. But heads took notice as Ghost Deni debuted his non-sequitur rap style that focused more on slang linguistics than easy to interpret rhymes (“Cauliflower hurting when I dumped the trash”). Ghost has shied away from explaining the lyrics, and maybe it’s better that way—Supreme is a walk down the halls of modern hip-hop abstractionism. —Insanul Ahmed