If you ever want the intelligentsia up in arms about aesthetics and the merits of conscious rap, bring up the subject over dinner. If you want to hear a Harlem barbershop hella vociferous with avowed expertise, mention some list compiled by a music mag. If you want to lose the lion’s share of a few nights’ sleep, pay serious consideration to rank one yourself. That was me over a few days in April as I prepared my list of the five all-time greatest rappers.
Rap music's origins trace back to the Bronx, where many of its pioneers were former members of crews or gangs and used battling as an alternative to actual violence as well as a way to foster esteem. Throughout its evolution, rap has retained its fiercely competitive nature, one whose artists tout themselves as the biggest, best, greatest. The “top five dead or alive”, that aggressive spirit makes it ripe for ranking. However, before delving into that realm, let's consider a few important points.
The criteria I use for my list are Skills, Content, Bona fides, and Impact. I must also disclose that I am quite critical of a significant portion of the new rap scene—the mumbling, the seeming de-emphasis on technical skills, and the mundane perspective that rap is merely a path to wealth. Furthermore, I don't advocate promoting obscure elements as a means to criticise the mainstream.
Jay's an exceptional storyteller and wordsmith, adept at creating powerful imagery, metaphors, and analogies. Moreover, he possesses a wide range of styles and is renowned for his insightful wisdom.
Jay has spent much time mining his backstory as a hustler and ascendance to rap’s first billionaire. He spoke his place in this pantheon into existence, rapping in hi-s “Grammy Family” freestyle, “Hov got flow though he’s no Big and Pac, but he’s close / How I’m ’posed to win? They got me fightin’ ghosts.” You’d be hard-pressed to find a better song about the hood than “Where I’m From.” His oeuvre also includes the daring 4:44, which plumbs his once-troubled marriage, and some of rap’s most memorable guest appearances, like his four- minute verse on DJ Khaled’s “God Did,” historicising America’s war on drugs.
Jay holds prestigious spots in the Songwriters Hall of Fame (as the first rapper ever) and the Rock & Roll Hall of Fame. He also holds the record for the most Billboard 200 No. 1 albums for solo acts and has won an impressive 24 Grammys in hip-hop, tying with Kanye for the most in the genre
The irrefutable successes of Roc-A-Fella Records, Rocawear, and Roc Nation have helped launch Kanye West and Rihanna into the stratosphere. His astronomical wealth in a genre born as an antidote to structural poverty—he proclaimed, “I’m out for presidents to represent me” on his first single—is an exemplar of manifesting a destiny.
Another rapper sans technical weakness. He can rap fast or slow; create unforgettable metaphors, and analogies as great as “Swimming Pools”; rivet us with storytelling à la “DUCKWORTH.” Kendrick demonstrates his versatility by adjusting his tone, delivering a softer vibe in songs like 'Auntie Diaries' or going all-out incendiary on Big Sean's 'Control': 'I'm in destruction mode if the gold exists / I'm as important as the Pope, I'm a Muslim on pork / I'm Makaveli's offspring, I'm the king of New York.
Each album is a concept—a day in his young life in Compton (good kid, m.A.A.d City), or a therapy session (Mr. Morale & the Big Steppers) exploring the uncommon territory of gender, toxic masculinity, and sexual abuse. He also spends as much time as any rapper inhabiting the interior lives of others. He rapped as a young woman on “Keisha’s Song” and was Nipsey Hussle on “The Heart Part 5.”
DAMN. made Kendrick the first artist outside classical or jazz to win a Pulitzer Prize. He’s won 17 Grammys, including three for Best Rap Album.
Despite not making it his sole focus, Kendrick has achieved tremendous mainstream success, with tracks like "Humble," "Bitch, Don't Kill My Vibe," and "Love" immediately springing to mind, though his most significant song is “Alright,” the unofficial anthem of Black Lives Matter. After a cosign from Dr. Dre and a classic debut, Kendrick seized the crown of the West Coast and is the most laureled and important rapper of his generation.
While Tupac may be considered the least technically gifted among the top five MCs, his go-to delivery—a melodic singsong—is undeniably the most distinctive in all of hip-hop. What he lacked in varied rhyme patterns and tropes he compensated for with passion, charisma galore, and a knack for selling what he said as scripture.
Pac left an indelible mark on rap with some of its most timeless songs: the anthemic "Dear Mama," the poignant "Brenda's Got a Baby" and "Keep Ya Head Up," alongside commercial hits like "California Love" and "How Do U Want It." Not to mention, he stirred up intense controversy with the fiery "Hit 'Em Up." Pac broke through on Digital Underground’s posse hit “Same Song” in 1991. He was killed five years later. In between, he served nine months in prison for sexual abuse, a sentence cut short by Suge Knight paying his seven-figure bail. Pac signed to Knight’s Death Row Records and released two albums, the first being his diamond-selling magnum opus All Eyez on Me. On “California Love,” its first single, he announced, “Out on bail fresh outta jail, California dreamin’ / Soon as I stepped on the scene, I’m hearin’ hoochies screamin’.”
Pac has sold more than 75 million albums—four released while he was alive, eight posthumous—and became the first solo rap artist in the Rock & Roll Hall of Fame.
Not only is Tupac one of the few figures known the world over by his first name, his lore seems eternal.
Biggie had a preternatural gift for language. The opening of “Who Shot Ya”: “Who shot ya? Separate the weak from the obsolete / Hard to creep them Brooklyn streets / It’s on ni%%*, fuck all that bickerin’ beef / I can hear sweat tricklin’ down your cheek.” He was a consummate storyteller, as evidenced in the booty-call-gone-bad tale of “I Got a Story to Tell”; could go from bravado to the self- deprecating candor of “Heartthrob—never / Black and ugly as ever.” Notably, he displayed his versatility, mastering any style, as demonstrated when he skillfully outrapped Bone Thugs-N-Harmony in their own signature style on 'Notorious Thugs.'
Biggie favored hyperbolic street tales but was an astute chronicler of hood hardships. (See “Juicy.”) And on a posse cut, his verse was the best verse—period. “I been had skills, Cristal spills / Hide bills in Brazil, about a mil, the ice grill” began his incredible verses on Puffy’s “It’s All About the Benjamins (Remix).”
He released just two albums—the ominous Ready to Die and the prophetic Life After Death (the latter a few weeks after his murder)—but each has sold more than 5 million. Add: First-ballot induction into the Rock & Roll Hall of Fame.
Premature death amplified Biggie’s legacy, but his living impact was also significant. He helped herald Lil’ Kim, a future icon in her own right, and was the luminous nexus of the Junior M.A.F.I.A. crew, whose debut album went gold. Had Biggie not been killed so young, he might’ve become the incontrovertible GOAT.
Wayne is a virtuosic wordsmith who began his career as an 11-year-old wunderkind on Cash Money Records. Like Biggie, there’s no style beyond his repertoire. He can sustain a narrative but seems more at home in the lyric—his verses luxuriate in image, metaphor, punchlines. On “A Milli” he raps, “A million here, a million there / Sicilian bitch with long hair, with coke in her derriere / Like smokin’ the thinnest air / I open the Lamborghini, hoping them crackers see me / Like, look at that bastard Weezy.” His drawl—made more pronounced in his syrup- sipping days—is inimitable.
Wayne has spent a helluva lot of his career boasting about his skills, threatening opps, testifying to the violence of his hometown, and boasting of his sexual prowess. He’s a notable contributor to some iconic Cash Money songs, including “Back That Thang Up” and “Bling, Bling.”
Twenty-one million albums sold. Nine platinum. Five Grammys, including the coveted Best Rap Album for Tha Carter III.
Wayne had one of the most successful runs in the history of mixtapes. He’s credited with launching Nicki Minaj and Drake, major artists by any measure. As Wayne, the biggest artist from the South’s most storied label, rapped on “Mr. Carter”: “The next time you mention Pac, Biggie, or Jay-Z / Don’t forget Weezy.”
My list. Why does it, or any damn list, even matter? Because hip-hop was born as a way for Black and brown people to fight oppression. Because what better way to assert worth than to be judged excellent if not the most excellent in a given field? The list of the top five all-time MCs counts because hip-hop is American. And greatness, or so the propaganda goes, is the American way.
