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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.

41

Scarface feat. Jay-Z, Beanie Sigel, “Guess Who’s Back” (2002)

Jay-Z told Cornel West that rappers like Scarface inspired his own honest, biographical approach. When the Houston rap legend reintroduced himself on 2002’s The Fix as an aging gangster with stories to tell, Jay-Z helped welcome the transition – in his autobiography, Scarface said the two MCs would “talk for hours.” With a glittering soul loop by Kanye West, “Guess Who’s Back” was summit between the East Coast, the South and the up-and-coming Midwest. During the making, Scarface was struck by how Jay laid down his enthused, vivid verse in one take. “I hate going in the studio with him,” he said to HipHopDX, “because he’s done with his shit before I sit down.” 

40

“Izzo (H.O.V.A.)” (2001)

One of Jay’s biggest early commercial hits – it peaked at Number Eight on the Billboard Hot 100 – this Kanye West-produced track features an exquisitely used sample from the Jackson 5’s soaring “I Want You Back.” “I grew up in the Marcy Projects in Brooklyn, and my mom and pop had an extensive record collection,” Jay told NPR’s Terry Gross in 2010. “So Michael Jackson and Stevie Wonder and all those sounds and souls – Motown etc., etc. – filled the house. So I was very familiar with the song when Kanye brought me the sample. It was just such an interesting and fresh take on it that I immediately was drawn to it.” 

39

“Come and Get Me” (1999)

Jay spits barely concealed threats in a dangerous game of reality-rap chicken, jumping into a casually fluent flow that feels as if it were coasting across the top of each kick drum on a surfboard. Timbaland provided the ambitious beat: Low-slung funk punctuated by wah-wah guitar for its first minute; a cinematic break narrated by ringing church bells and an uneasy flute; and then a robo-digi-funk groove. 

38

Jay-Z and Kanye West, “Gotta Have It” (2011)

If Watch the Throne was Jay and Kanye’s attempt at tag-team rap, “Gotta Have It” is assuredly its crowning achievement. Produced by West and the Neptunes, the cut is built around three chopped-up James Brown samples and finds the rappers completing each other’s sentences, butting in mid-flow if necessary. Like many tracks on the album, catchphrases and meme-worthy utterances obscure a more profound, deeper sentiment. “I wish I could give you this feeling/I’m playing on a million,” Jay professes to the less fortunate, a shipwreck survivor rowing to shore knowing the lifeboat couldn’t contain everyone. “Gotta Have It,” like the entire album, may read as straight exuberance. But as Jay noted to the New York TimesT magazine, “It’s a lot of pain and a lot of hurt and a lot of things going on beyond, beneath that.”  

37

“Who You Wit II” (1997)

Roc-A-Fella co-founder Dame Dash was working on a soundtrack to a new comedy called Sprung when he asked producer David “Ski Beatz” Willis for original material. The next day, the producer began to flip smooth jazz group the Jeff Lorber Fusion’s 1981 song “Night Love” (featuring a young Kenny G) into “Who You Wit.” With an extra verse, re-released as “Who You Wit II,” it would become one of the most cherished, punchline-heavy songs on Jay’s second album In My Lifetime, Vol. 1. “‘Who You Wit’ leaves a legacy of true lyricism at its purest form,” Ski tells Rolling Stone. “People gravitated to that song because it was so witty.” “The arrangement had a lot of space and was somewhat minimalistic, [making] it easier for them to manipulate [the sample] the way they did,” Lorber adds. “It was a little shocking to hear my song in a new context, but i think it has aged well and is still fun to listen to.”

36

Jay-Z and Beanie Sigal feat. Scarface, “This Can’t Be Life” (2000)

An early Roc-A-Fella beat from Kanye West relied on disembodied vocal samples crying out from soul music history, while Jay – then a notoriously callous rapper – delivers a touching reflection on the painful origins for his show business pursuits and passions. It’s no slight to him to suggest Beanie Sigel and Scarface steal the show. The song’s a powerful rendering of the nuances and complexities of pain, Beanie showing it through a lens of exhaustion (“I’m tired of trying to hide my pain behind the syrups and pills”) and Scarface managing to envelop love, spirituality, community and loss on the head of a pin.

35

Beyoncé feat Jay-Z, “Crazy in Love” (2003)

The night before Beyoncé turned in her 2003 debut Dangerously in Love, she asked Jay-Z for a favor. He heard the hit potential in “Crazy in Love” immediately; how those Chi-Lites horns and producer Rich Harrison’s go-go percussion could catapult the Destiny’s Child singer to solo stardom. “He played the song and went crazy,” Young Guru, Jay’s personal engineer, said to MTV News. “Crazy in Love” would be the breakout moment for Bey, topping the Billboard Hot 100 for eight weeks – though a big asset ended up being the chemistry between the then-rumored couple. She oozes sex appeal, while he raps about chinchilla furs in a futile effort to keep his cool. 

34

Jay-Z, Beanie Sigel and Memphis Bleek feat. Freeway, “1-900-Hustler” (1999)

The Bink!-produced “1-900-Hustler” was a high-concept rap record featuring four present-and-future Roc-A-Fella rappers sharing advice on how to hustle – an idea borrowed from Texas rap heros the Convicts’ 1991 record “1-900-Dial-A-Crook.” Wed to a fiery sample of Ten Wheel Drive’s “Ain’t Gonna Happen” (the rappers all apparently rapped over the part that Bink! meant for the chorus), the song’s highlights are many: Jay charges $800 for a phone call asking for advice; Beanie Sigel sends a hustler to the “bullshit-ass elevator music” for talking about illegal work over the phone; Freeway spits his advice before concluding the best lesson would be just to rob the caller himself.

33

“Threat” (2003)

Jay-Z wanted his retirement album to show that he was leaving hip-hop in fighting shape. So all pressure was on new collaborator 9th Wonder of hot underground group Little Brother, who came on board to produce “Threat” after he tried booking DJ Premier. “Now you can argue this,” 9th told Complex, “but what he was trying to tell me in so many words was, ‘I want you to be like what Premo was to me on my other albums.’ And I was like, ‘Whoa, you’re going too far now, Jay.'” But 9th pushed himself, as he flipped an R. Kelly sample, added piano stabs and cued silences to punctuate Hov’s winding, heart-stopping wordplay.

32

“A Week Ago” feat. Too $hort (1998)

Vol. 2… Hard Knock Life exploded with splashy radio anthems, becoming Jay-Z’s only album to be certified five times platinum. “A Week Ago,” however, was the album’s throwback to the rueful street tales that he built his reputation on. Bay Area trailblazer Too $hort wasn’t supposed to be the only regional rap legend on the track – Jay asked Pimp C to appear, according to his UGK partner Bun B. The session fell through, but Jay linked up with UGK a year later for the far more famous “Big Pimpin’.”