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.
“Roc Boys (And the Winner Is…)” reaches back to the dazzling, horn-blasting sound of iconic Jay-Z hits like “U Don’t Know.” Gleaming brass lines ricochet around the track – produced by P. Diddy and the Hitmen – and Jay-Z raps about amassing vast wealth: “Let ya hair down baby, I just hit a score/Pick any place on the planet, pick a shore/Take what the Forbes figure, then figure more.” One group that got to share the wealth was the Brooklyn soul outfit the Menahan Street Band, who were sampled for the track. “A record being sampled is like a needle in the haystack, and the chances of it being a hit song is even slimmer, so it was a real fortunate thing that happened to us,” the group’s guitarist and leader Thomas Brenneck told Life and Times. “Then being credited as a songwriter on a Jay-Z song does a lot for the songwriters. Up until then our records sold 5,000-10,000 copies; [2007 LP] American Gangster sold a million copies. It was a real boost in self-esteem.”
Jay-Z was hip-hop’s Grateful Dead – despite having “retired,” he couldn’t bear saying goodbye to the game. In 2003, Jay and Linkin Park capitalized off the burgeoning MP3 “mashup” culture with an MTV special, followed by the six-song EP Collision Course. What could have been an empty cash grab ended up feeling sincere. Lone single “Numb/Encore” especially captured everyone’s delight over how well their music actually fit together. “I’m not trying to be you, you’re not trying to be. There’s fusion and just whatever happens, happens. I love that,” Jay said to Linkin Park lead singer Chester Bennington on MTV. Since Bennington’s death in July, Jay has performed “Numb/Encore” several times in tribute, turning the single into a bittersweet farewell.
“It was a song that Kanye and I had done first; me featuring Kanye,” T.I. told MTV. “An idea had presented itself: ‘What if we included these people and made it an event record?’ I was like, ‘That’s a very ambitious idea, but a lovely one.'” In 2008, “Swagga Like Us” represented a summit of rappers – T.I., Lil Wayne and Kanye West – all in the middle of remarkable stretches of hit-making, joining forces with Jay-Z, who had helped to clear the way for their pop crossover success with his own hot streak in the late Nineties and early 2000s. Each MC takes turns rapping as a blithe sample of M.I.A.’s “Paper Planes” cycles through the background. Jay-Z sounds at ease, unruffled by the star power of his collaborators and casually dismissive of everyone else. “Can’t teach you my swag,” he raps. “You can pay for school, but you can’t buy class.”
“Ain’t No Nigga” might be the most shamelessly commercial track on Jay-Z’s debut, Reasonable Doubt, and it’s naturally the one that elevated him from Brooklyn thug poet to future pop dominance. Initially released as the B-side to “Dead Presidents,” it found a national audience when the rapper’s Roc-A-Fella team switched distribution from Freeze/Priority Records to Def Jam, and the latter selected it as a single for Eddie Murphy’s The Nutty Professor soundtrack. Jay’s verses are nice – “They say sex is a weapon/So when I shoot, meet your death in less than eight seconds,” he brags. But he meets his match thanks to a riposte from a then-teenaged Foxy Brown.
By at least one measure, “Empire State of Mind” is the biggest record of Jay-Z’s career: He had never topped the Hot 100 as a lead artist until he released this collaboration with Alicia Keys, the final Number One hit of the 2000s. “Jay hit me up like, ‘I feel like I have this record that’s going to be the anthem of New York,'” Keys, another Big Apple native, explained to MTV. “He’s like, ‘The piano, the way the style [is], the whole flow, and it couldn’t be the anthem of New York without you.'” “Empire State of Mind” loops the dramatic, golden opening motif from a towering slice of orchestral soul – in this case, the Moments’ “Love on a Two-Way Street” – to great effect. Jay-Z touts his credentials as the “new Sinatra,” while Keys aims for universal uplift: “These streets will make you feel brand new/Big lights will inspire you.”
Jay-Z was in his imperial phase when New York rap was doing the same, but as a true student of history, he looked the country over for inspiration, appearing on No Limit releases like the I Got the Hook-Up soundtrack and inviting underground regional heroes UGK and a newly minted multi-platinum superstar from New Orleans named Juvenile to appear on 1999’s Vol. 3. Though Juvenile only appears on the song’s hook, his sonorous Southern drawl framed one of Timbaland’s most unsettling beats with a menacing melody. As searing synths tore a hole in the stratosphere, Jay rapped with the impenetrable, brutal confidence of a world – from New York to Houston to Miami to Atlanta – which folded before him, violence and success its only currency.
Reasonable Doubt is suffused with a mixture of regret and pride at Jay-Z’s street exploits. The two conflicting emotions can be difficult to parse, which may have led some early critics to dismiss it as an above-average gangsta rap record upon its initial release. Produced by Ski Beatz, who flips a Stylistics sample and lends the track a smooth, melancholy tone, “Politics As Usual” epitomizes this quandary: Jay rhymes how he’s “cursing the very God that brought this grief to be,” but then shifts and says, “I’m trying to feel mink, nigga.” “I remember even the reviews, when it first came out, ‘This is gangsta, hustler persona.’ I knew they didn’t understand what was being said in the music,” he told the BBC for its 2008 documentary series Classic Albums. While inner turmoil about the hustler’s life has been a hallmark of hip-hop since the days of Ice-T, Jay’s use of language elevates songs like “Politics As Usual,” and justifies Barry Michael Cooper’s assessment of him as “the Proust of the projects.”
The Just Blaze-produced “Song Cry” features a particularly wrenching performance from Jay. Offset by an interpolation from Bobby Glenn’s 1976 ballad “Sounds Like a Love Song,” he embarks on a world-weary lament, looking harshly at the effects a demanding tour schedule and roving eye are having on his relationships. The lyrics, which represent what Jay-Z called a “gumbo of a lot of my relationships” in a 2005 GQ interview, are “about a guy who isn’t fully ready to commit, but the girl he’s with, he really loves her, you know? And he wants to be with her. So what happens is, she’s sick of putting up with his stuff and she finally moves on into another relationship and he’s crushed. But even after all that, his pride won’t allow him to cry. … So you’ve gotta make the song cry.”
Kanye West acknowledged how impressed he was this Jay-Z verse on 2007’s “Big Brother”: “On that ‘Diamonds’ remix I swore I spazzed/Then my big brother came through and kicked my ass.” The friendship and rivalry between Jay-Z and his former producer has been the source of lots of great music since the two began working together at the dawn of the new millennium. “Diamonds From Sierra Leone (Remix)” remains one of their pluckiest collaborations, an audacious merger of old-school pomp – the in-your-face sample of Shirley Bassey’s over-the-top James Bond theme – and a sleek synth-pop sound that hints at West’s upcoming pivot into dance music. West raps with focus and dexterity here before passing the baton to Jay-Z for a scorching verse, the origin of one of his most famous lines: “I’m not a businessman, I’m a business, man.”
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.”
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.”
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.
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 Times‘ T magazine, “It’s a lot of pain and a lot of hurt and a lot of things going on beyond, beneath that.”
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.”
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.
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.
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.
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.
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’.”
Jay-Z’s retirement was brief and full of wonderful interruptions like “Dear Summer,” which appeared on Memphis Bleek’s 534 album but did not include a verse from Bleek himself. Producer Just Blaze sets aside his trademark stadium-leveling sound to make a cooled-out beat based around a barely-tweaked excerpt from jazz-funker Weldon Irvine’s “Morning Sunrise.” Jay-Z originally debuted the lyrics to “Dear Summer” – a love song about the rapper’s propensity for warm-weather hits – during a visit to New York’s Hot 97. “The record is so crazy we was going to put it out the day after he went to radio, but Jay was like, ‘Nah, chill,'” Just Blaze told MTV. “Doing that record was kinda like old times. It was nobody in the room but me, Guru [the engineer] and Jay. … Obviously, the artist bug is still there,” Just Blaze added. “It’s not like he needs to do the intro to Bleek’s album. When you’re an artist, you’re always gonna be an artist even if that’s not your main job anymore.”
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.”