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Jay-Z: 50 Greatest Songs

With a rhyme career going since the late Eighties, Jay-Z’s songs have been reflective, pop, confessional, hard-edged and indelible. Here are his best

Is Jay-Z the greatest rapper of all time? “I’ve got this Elvis thing going on right here,” Jay-Z told Rolling Stone in 2007 shortly before tying the King’s record of 10 albums debuting at Number One (and well before notching four more in the following decade). Indeed, Jay-Z’s feats are many: 21 Grammys, toasted by Barack Obama as the first rapper in the Songwriters Hall of Fame, and represented in countless rappers’ Top Fives (Kendrick Lamar, T.I., J. Cole among them; and Lil Wayne has a Jay-Z verse tattooed on his leg). He looms large in skills, impact, business acumen: the cool yet distant image of a former street hustler, a flow that’s both technically advanced and pop savvy and an unimaginable wealth that Forbes and other publications struggle to calculate. Yet even among the musical largess that comprises Jay, some of his classic songs rise above others. Here’s our list of his 50 greatest.

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The Jaz feat. Jay-Z, “The Originators” (1990)

At the age of 21, Jay-Z was mostly paying dues, whether sleeping on Big Daddy Kane’s tour bus for a chance to spit a verse or two in concert, or slinging drugs in Brooklyn and Trenton, New Jersey. Luckily, his Marcy Projects friend and mentor Jonathan “The Jaz” Burks enjoyed a label deal with EMI. “When Jaz scooped me up from the projects, I was young,” he told Blaze magazine in 1998. “I was just his man, and he brought me along for the whole ride.” Jay-Z landed cameos on both of the Jaz’s albums, including the kitschy minor hit “Hawaiian Sophie.” But it’s the 1990 single “The Originators,” which found the two joining forces on an Afrocentric-themed fast-rap fusillade that hints at Jay-Z’s future mastery of a cool, dexterous verbal style. Over a funky James Brown loop, he works a stutter-step flow to punch out rhymes like “Stop fakin ya makin’ it, son/I’m breakin’ a-breakin’ a-breakin’ ya tongue/Don’t get caught perpetratin’ the cool ones.”