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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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“Hard Knock Life (Ghetto Anthem)” (1998)

For Jay-Z’s first single to break into the Top 15 of the pop charts, producer Mark “The 45 King” famously flipped an indelible tune from the Annie Broadway soundtrack – he copped the record from the Salvation Army for a quarter after seeing an ad on TV. He gave a dubplate to Kid Capri, who was DJing Puff Daddy’s No Way Out Tour. “Fans were running up saying, ‘How did you get the Annie song behind the drums?’ It was mostly white people coming up to me,” Capri told Grantland. “I knew from the reaction I was getting that it was really working.” Eventually Jay asked too, and thus began this monster hit, a vivid, melancholy look at his rise from “from lukewarm to hot; sleepin’ on futons and cots/to king size.” “I wasn’t worried about the clash between the hard lyrics and the image of redheaded Annie,” Jay wrote in Decoded. “Instead, I found the mirror between the two stories – that Annie’s story was mine, and mine was hers, and the song was the place where our experiences weren’t contradictions, just different dimensions of the same reality.”

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“Nigga What, Nigga Who (Originator ’99)” feat. Big Jaz (1999)

After Jay-Z became a star, he invited his old friend and mentor the Jaz – now credited as Big Jaz – to appear on a sequel to their 1990 rapidfire flow clinic “The Originator.” “[W]e was using that fast style that everybody seems to be using now,” Jay said in the liner notes to Vol. 2… Hard Knock Life. Where Jay and Jaz practiced their fast flows over relaxed, jazzy production in 1990, their 1998 reunion took place on a spacey, futuristic track by Timbaland. Timbo had already changed the sound of R&B with Aaliyah and backed Missy Elliott’s playful, creative hip-hop, but this was a pivotal moment in his career, the first time an elite MC had a speedy flow to match the busy ticking of his hi-hat patterns. 

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“Public Service Announcement” (2003)

Jay-Z had to actually stop The Black Album from being pressed to include this anthemic, last-minute reintroduction. Throughout, he answers to a journalist who had just sat through an album listening session, only to ask how he could pair a Che Guevara T-shirt with a chain. “Che’s failures were bloody and his contradictions frustrating,” Jay-Z writes in Decoded. “But to have contradictions – especially when you’re fighting for your life – is human, and to wear the Che shirt and the platinum and diamonds together is honest.” Setting the stage is producer Just Blaze, with ominous keys and a spoken-word intro (“Fellow Americans…”) fit for a revolutionary about to perform at Madison Square Garden. 

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“Brooklyn’s Finest” feat. The Notorious B.I.G. (1996)

“Brooklyn’s Finest” remains a magnificent document of two Brooklyn greats together in peak form. Jay-Z and the Notorious B.I.G. were developing a new group with Biggie’s girlfriend Charli Baltimore called the Commission. “For the next year, we weren’t only talking about plans for the Commission,” Jay-Z told XXL in 1998. “He had so many plans for [Life After Death], with touring and relocating and moving around.” Instead, Biggie was murdered in March of 1997. This song sounds like the opening chapter in a partnership that never reached fruition. Kicking off with Wayne “Pain in Da Ass” Hirschorn’s interpolation of Al Pacino’s over-the-top performance in Carlito’s Way, Biggie and Jay trade ever more ridiculous crime boasts: Jay drops the immortal line, “Peep the style and the way the cops sweat us,” while Biggie claims he’ll “shoot your daughter in the calf muscle.” The song’s most famous moment comes when Biggie tries to answer 2Pac’s spurious “Hit ‘Em Up” claims of sleeping with his estranged wife Faith Evans: “If Fay have twins, she’d probably have two Pacs/Get it, 2Pac’s?” 

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“U Don’t Know” (2001)

Just Blaze’s pairing of room-shaking bass and a sped-up sample of funk pioneer Bobby Byrd’s 1970 scorcher “I’m Not to Blame” act as a momentous springboard for Jay’s boasting about his various business successes – his drug-slinging days in “Hell, where you are welcome to sell,” and the growth of his Roc-A-Fella empire into one that can “smarten up, open the market up” into unexpected avenues like clothing. Jay thunders “Motherfucker, I – will – not – lose” as the music drops out before the fourth verse. It’s a stunning moment where his confidence explodes into triumphant catharsis. 

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“99 Problems” (2004)

Jay-Z paid Rick Rubin a visit to “recapture that feeling I had when I was a kid,” as he explained in documentary Fade to Black. What came out of that session did have vintage heavy metal riffery reminiscent of Rubin’s Eighties work with LL Cool J and Beastie Boys, but lyrically it was a blistering, modern-day critique, taking aim at those who demonize him as a black man and rapper. The hook, borrowed from Ice-T and Brother Marquis of 2 Live Crew – “I got 99 problems but a bitch ain’t one” – was bait for talking heads, since verses play with the other meanings of the word. “[E]ven as I was recording it, I knew someone, somewhere would say ‘Aha, there he goes talking about them hoes and bitches again!'” Jay writes in Decoded. The song became iconic enough that Barack Obama brought it to the 2013 White House Correspondents Dinner: In light of Jay and Bey’s controversial visit to Cuba, he said, “I’ve got 99 problems and now Jay-Z is one,” to hearty laughs.

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“Big Pimpin'” feat. UGK (2000)

When the Mariah Carey-stamped single “Things That U Do” failed to pick up on the charts in its first two months as a single off Jay’s Vol. 3, he and Dame Dash quickly moved to the Timbaland-produced exotica of “Big Pimpin'” – which successfully sold the world’s second-oldest profession as a jet-setting, champagne-popping lifestyle. And an exuberant one at that, from the beat’s flamboyant Best of Bellydance From Morocco, Egypt, Lebanon, Turkey origins (Timbaland was later sued for his sample of Baligh Hamdi’s “Khusara Khusara”) to Hype Williams’ lavish video, shot at Carnival in Trindad (and, when Pimp C skipped that shoot, a similar-looking location stateside). Inspired by the Pretty Tony character from 1973 film The Mack, Jay’s verse is him at his unaffected, bulletproof coldest. For UGK’s Bun B and Pimp C, it was their first moment to show out in such a high profile spot. Bun’s bars (“step up your vocab”) proved as memorable as Jay’s, and Pimp C’s Big Gipp-inspired flow offered a raw, uncut coda.

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“Dead Presidents II” (1996)

Released in February 1996, the original “Dead Presidents” found Jay-Z twisting lyrics about fake thugs “scared to throw your toast,” and spouting claims about “representing infinity with presidencies,” all in a deftly loquacious style that bore the hallmarks of peak Mafioso rap. But when his debut Reasonable Doubt dropped later that June, he offered two fresh verses that plumbed deeper subject matter. He alludes to the shooting of DeHaven Irby, a childhood friend who taught him the drug game (“On the uptown high block he got his side sprayed up”) and recalls how he dodged a few deadly shots of his own (“I had near brushes, not to mention, three shots close range”). He weaves notes on his baller superiority (“Roc-A-Fella, don’t get it corrected, this shit is perfected”) with biographical asides, making for a poignant and superior sequel. Producer Ski Beatz’ blend of Lonnie Liston Smith’s “A Garden of Peace” with Nas’ “The World Is Yours” laid the groundwork for future drama. “I just threw that sample in there to see if it worked because I liked Nas’ voice,” Ski told Complex in 2010. But when Nas turned down Jay’s offer to re-do the chorus – AZ appeared in the “Dead Presidents” video instead – it led to one of the greatest rivalries in hip-hop history.

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“Where I’m From” (1997)

Producer Ron “Amen-Ra” Lawrence was record-hunting in 1996 when he found soul singer Yvonne Fair’s “Let Your Hair Down” and tried, as he tells Rolling Stone, “giving it a sinister soundtrack feel.” The track, which Diddy originally passed on, was still in rough form – no sound effects, no extra percussion. But when Jay-Z heard what would become “Where I’m From,” the rapper, inspired, immediately began recording his personal verses two bars at a time. “It gave me a vision to make the track sound more dramatic based on Jay’s flow,” Lawrence says.

The result is one of Jay’s most candid and intimate tracks; part memoir, part cultural and socioeconomic critique, part distillation of his surroundings both past and present. “He painted a grim picture about Marcy Projects,” Lawrence says. “It gave the listener a mental vision of what it was like for him growing up there in Brooklyn.”

From the blunt, unforgiving song’s opening line – “I’m from where the hammers rung /News cameras never come” – Jay describes a place where “life expectancy is so low, we making out wills at 18.” It’s the inverse of “Imaginary Player,” where decadent luxury takes a backseat to day-by-day survival. “Where I’m From” also boasts some of Jay’s most packed couplets: “Where how you get rid of guys who step out of line, your rep solidifies/ So tell me when I rap, you think I give a fuck who criticize?” 

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