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, sixteen with M-16's and ten 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, no doubt 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, Andre 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 Andre 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 (@Incilin)