Welcome to PLAYLIST, a re-occurring feature where our staff creates a playlist (with mix tapes and CDs becoming so unfortunately passé) centered around one artist or band with a deep catalog. For each LP we choose one song and pick a writer to rhapsodize its virtue.

This feature is especially challenging when facing the discography of Jay-Z. In a career that has lasted a decade and a half, Jay-Z has risen to become a major force in the hip hop industry, moving from MC to major label executive. And not everyone gets to marry Beyonce Knowles. With so many career defining songs, picking just one per album is nearly impossible. But we tried our damnedest.


“Brooklyn’s Finest” from Reasonable Doubt (1996)

What can be said about this song that hasn’t been repeated often and thoroughly in the streets as it has in print? Few people would dare knock Jiggaman’s debut, and on an album full of bangers, “Brooklyn’s Finest” is a cut above. Not many could ever hold their own with Biggie Smalls; he was a force of nature, with a voice so booming and a mind so sharp it seemed effortless. To have him on a track was to ensure he would eat it up, so it came as a pleasant surprise that not only did Jay-Z hold his own, his verses are complementary to Biggie’s while maintaining a presence.

Producer Clark Kent’s tinkly, staccato beat is like an elegant machine gun, coming with enough force to put Biggie and Jay-Z’s voices at the forefront. Biggie’s booming flow is supplemented by Jay-Z’s more fluid delivery, and it creates a perfect interrelation that has hardly ever been touched by any collaborator since. The success of the song doesn’t come from their rivalry- in fact they sound like shooters on the same side, blasting haters and listeners away with their powerful rhymes. It’s scary, to boot – the quick interchange between their verses coupled with the beat’s climbing tempo gives it an immediacy that is unparalleled, almost like the soundtrack to a robbery

It’s rare that hubris in rap sounds believable; in a culture built around braggadocio, way more fall flat than ever actually back it up. Jay-Z embraced being associated with New York and its lifestyle, and on “Brooklyn’s Finest” we see the seeds of a young hustler who would intern under a kingpin and eventually ascend his throne. – Rafael Gaitan


“Streets is Watching” from In My Lifetime, Vol.1 (1997)

Following Reasonable Doubt, a debut that defined his voice in a crowded genre, Jay-Z returned one year later with In My Lifetime, Vol. 1 which found him trying to find a niche for said voice within an overproduced shiny suit-wearing soundscape. But while the glossier moments, courtesy of appearances from Babyface, Blackstreet and Puff Daddy, show glimpses of his crossover potential, Jay made certain to keep his core street audience satisfied and kept the album packed with gritty bangers like “Streets is Watching.”

Produced by Ski, one half of early-’90s group Original Flavor (who in 1992 gave Jay his first major label guest appearance on “Can I Get Open”), “Streets is Watching” is a relaxed but ominous account of an exhausted but dedicated kingpin at the top of his throne. Over a sample of Labi Siffre’s “I Got The…,” (a song later used by Dr. Dre for Eminem’s “My Name Is..”) it begins with one of the most quoted Jay-Z lines: “Look, if I shoot you, I’m brainless/ But if you shoot me, then you famous/ What’s a n*gga to do?” It’s a sentiment eerily prophetic of the numerous wars on wax he would be goaded into over the course of his career. Jay’s oft-changing flow both maintains the ever-changing hyper-aware atmosphere of the narrative as well as puts all of his undeniable skills on display. The song became strong enough to serve as the basis for a direct-to-video film adaptation that weaved together a story through scenes filmed to link all of Jay’s previous music videos. By making this jump into the self-released film territory after seeing Master P’s success with I’m Bout It, the film became the first expansion beyond music that saw Roc-A-Fella moving towards becoming a multimedia entertainment juggernaut. – Chaz Kangas


“Hard Knock Life” from Vol 2: Hard Knock Life (1998)

Jay-Z is indisputably the ruler of his own universe, a kingdom which comprises concrete boundaries (Roc-A-Fella Records, his own mind) and imaginary ones (New York City, the rest of the rap world). He flexes this perceived power without compunction – it’s no coincidence he calls himself J-Hova – and over the years has expressed it in a variety of ways, from an arrogant treatment of rivals to sneering derision of trends and styles. One of the most entertaining examples is the way he opens songs with blithe, haughty expressions of self-satisfaction, like the insouciant “check the bassline out” at the beginning of “Hard Knock Life.”

This is the first sign of what a magical experience Jay-Z’s first big hit is going to be. He takes what is, in my mind, one of the most annoying songs on the planet, and condenses its shrill, foot-stomping indignation into a sharply strident send-up of his own impoverished youth, as well as his fast ascension to dizzying wealth. Jay-Z might not have been a red-haired singing orphan, but he still started off dirt poor, a fact that neither he (nor any other rags-to-riches rapper) is ever going to let us forget, especially as it accentuates the growing disparity between his humble beginnings and steadily growing prestige.

If most rappers are really just foul-mouthed, drug-dealing 21st century Horatio Algers, then “Hard Knock Life” helps to establish Jay-Z as their unofficial leader, a determined perfectionist whose steely-eyed lyrical precision helps turn one of hip-hop’s most bizarre samples into a deserved smash. – Jesse Cataldo


“So Ghetto” from Vol. 3… Life and Times of S. Carter (1999)

Boasting in interviews that he was attempting to channel Michael Jackson’s Thriller for inspiration, Jay was aiming for every song on Vol. 3 to be an absolute classic. While the first single “Do It Again (Put Ya Hands Up)” wasn’t quite the across-the-board smash his previous singles had been, its follow-up “Big Pimpin” spent a decade as Jay’s signature song. Today, Vol. 3 sounds like the manifesto written by an artist at a time when both he and his genre was undergoing a significant transition. Along with being ahead of the curve in terms of being one of the few New York rap albums featuring appearances from Southern rappers like UGK and Juvenile shortly before the South moved to the genre’s forefront, it was also one of the first casualties of the file-sharing era that saw a month-early leak force Jay to change his tracklisting at the last second.

The album also marked the last time he would work with one of his signature collaborators, DJ Premier. The fallout between the two directly goes back to “So Ghetto.” While Jay wanted to give it one of his sing-along refrains, Premier pushed to instead have his signature scratch-hook for the chorus. The resulting compromise may not have been what the two parties involved wanted, but for the rest of us it’s a best of both worlds centerpiece of an album where Jay had never been a better rapper. While the core of the song is about how you can’t take the ‘hood out of the multimillionaire, there’s a subtext to it that shows a certain self-awareness of Jay’s aspirations to achieve levels of success not seen from people who do what he does. While he masks it with humor (“Saw him cruising in a car with this bougie broad/ She say ‘Jigga-man you rich, take that doorag off!’“) and emphasizes he “won’t change for no paper,” it sounds as much like he’s trying to convince himself as the listener, and its effortless delivery shows Jay himself knows this all too well. – Chaz Kangas


“This Can’t Be Life (ft. Beanie Sigel and Scarface)” from The Dynasty (2000)

Like any good tycoon, Jay-Z has a knack for packaging his origins as a product, turning former hardships into current selling points symbolic of the natural swagger that comes from rising out of adversity. Written as a bleak yet optimistic glimpse into Jay-Z’s early days, when he thought, “Damn, I’ma be a failure,” as he was “Surrounded by thugs, drugs and drug/ Paraphernalia,” “This Can’t Be Life” is the Jay-Z brand as motivational tool. Recognizing the OG bonafides that past gives him even as he details how he was going nowhere until he rose above those thug characteristics, “This Can’t Be Life” is a keen bit of salesmanship, hinging on the juxtaposition of a glorified criminal past and the knowledge that true success only comes when such distractions are cast aside.

Sweetening the pot even more is Kanye West’s beat, a catchy but unobtrusive affair that leaves plenty of room for Jay-Z’s narrative, as well as those of guests Beanie Sigel and Scarface. Leaning heavily on a brief, pitchshifted snippet from Harold Melvin & the Blue Notes’ “I Miss You,” West’s production is the perfect mixture of melancholy and hopeful, gracefully expanding on the emotions of the personal stories Jay-Z, Sigel and Scarface exchange. A message track that doesn’t belittle its audience or lose itself in a schmaltzy, melodramatic production, “This Can’t Be Life” is a product any hip-hop consumer can get behind. – Nick Hanover


“Izzo (H.O.V.A.)” from The Blueprint (2001)

The Blueprint may have dropped on the wrong date (9/11/01), but it is now venerated as one of Jay-Z’s best records. It is full of songs from a man at his creative peak, from the Nas takedown “Takeover” to the soulful “Song Cry,” a collection of tracks of unwavering braggadocio decked out in the lush production of Kanye West and Just Blaze. Lead single “Izzo (H.O.V.A.)” remains the best song on an album full of classics. Released weeks before The Blueprint came out, the song became so popular that Def Jam rushed the album out to stop bootleggers from selling the single. Looking back, however, Jay-Z must share credit with fledgling producer Kanye West, anything but a household name at the time.

Thanks to an instant hook (Hova and Kanye sample “I Want You Back” by the Jackson 5), “Izzo (H.O.V.A)” comes on like a song that has been with us since little Michael Jackson and his brothers broke hearts with the melody back in 1969. But “Izzo (H.O.V.A.)” is anything but a love song. In the song, Jay-Z chronicles his pre-rap days as a drug dealer in its first verse. Fast forward into the second verse and Jay-Z is fighting off the predators in the music industry before returning to the Marcy project of his youth where he recognizes the success that pulled him out of it all.

But it’s the chorus, with its sweeping Jackson 5 hook, that makes the song so damned infectious. Back in 2001, “H to the izz-O, V to the izz-A/ Fo’ shizzle my nizzle used to dribble down in VA/ H to the izz-O, V to the izz-A/ That’s the anthem get’cha damn hands up,” blared from speakers from New York to Los Angeles. It hasn’t aged a day. I wonder how long it took people to figure out he was just spelling out his damned name. – David Harris


“The Watcher 2” from The Blueprint 2: The Gift (2002)

Though it can be hard to sift through all the tunes on The Blueprint 2, “The Watcher 2” instantly stands out as one of the best. Sonically, it shares a lot of space with hits from The Blueprint and The Dynasty, with a clean, slick production value bolstering the funky groove at its core. Punctuated by staccato horns and a spaghetti western guitar riff, Jay muses on (like he does so many times) the state of the mainstream rap game that he helped to build; the lyrics cut into the gangster posturing that was infecting hip-hop in the early ’00s (and well before that). Verse after verse sees him taking on the youngsters of hip-hop, spitting venom to those fresh-faced kids with a tough outer shell. “All these rap singers claimin’ they bangers/ Doing all sorts of twisted shit with they fingers/ Disrespectin’ the game, no home trainin’ or manners/ I was doing this shit when you was shittin’ in Pampers” he spouts, calling out the authenticity of the juvenile hip-hop core. At this time in his career, The Blueprint 2 falls right in the middle of his discography-he could get away with lines like that without sounding like the tired cliché he does on a few future releases. Though he had already garnered significant critical and mainstream acclaim, the street mentality of his earliest records was still fresh, relevant and invigorating, and this track is a perfect example. It may not be a game-changing tune like “99 Problems” or “Brooklyn’s Finest,” but “The Watcher 2” is a tightly-delivered amalgamation of just about everything that Jay-Z does better than most: slick delivery, fine production and an arrogant sense of pride. – Kyle Fowle


“The Blueprint 2” from The Blueprint 2: The Curse (2002)

Let’s be real, The Blueprint 2 is not a good album. As with most sequels, it is overlong and commercial. Most of the tracks feel too commercial and uninspired, failing to capture the spirit of the original. There are genuine moments of Jigga’s brilliance, such as title track “Blueprint 2.” Featuring a haunting vocal loop, Jigga sounds fierce as ever, perhaps realizing he needed to wake the audience up midway through. As he states on the chorus several times, “I got my mojo back/ Oh, behave” (it was relevant at the time, so it’s not an eyeroll-worthy joke.) His flow is passionate and confident, sounding almost as hungry as he did in ’96. A rapper of Jay-Z’s statue always has challengers, so “Blueprint 2” is his reminder that he’s still the same guy from Marcy who doesn’t let heat go unanswered.

Producer Charlemagne laces Jigga with a slick beat, flipping Ennio Morricone’s “Ecstacy of Gold” into a swirling and atmospheric beat that is the perfect companion to a standout song, as well as one of the more unique samples in mainstream hip-hop. Jay-Z also manages to include shots at several of his haters, including Nas and Jaz-O. Sounding as reinvigorated in the feud as Nas was with his standout “Ether,” lines such as “My mama can’t save you this time/ Niggas is history// Who you know flow as vicious as me?” prove that even though Jay-Z seemed to be slumming it on this go-around, he’s always got a plan for his detractors and foes alike. – Rafael Gaitan


“99 Problems” from The Black Album (2003)

It’s fun to listen to this song and try to numerate all the problems Jay-Z must be suffering from, especially because most of the ones he mentions here seem to have already been resolved. Like most of his tracks, the problem presented is really a feint, an excuse to parade out his long history of victories over adversity; it also acts as a subtle bit of misdirection. The lack of a ‘bitch’ problem not only points out Jay-Z’s superiority over the rest of us losers, but makes us wonder why he’s so hung up on mentioning it. This is presumably because a) like Snoop Dog, and as he points out again later in the album, Jay-Z doesn’t love hos and b) he’s dating Beyonce, which this song seems to be tacitly bragging about.

Stripping down his sound after the steadily diminishing returns of the Blueprint projects, The Black Album finds hip-hop’s unofficial CEO on a kind of working vacation, an album that makes implausible threats about retirement while making assuring we would miss Jay-Z if he actually left. “99 Problems” is probably the best example, a third single that should have been the album’s lead, all righteous anger and proud disgust. The lack of girl problems leaves him with a lot of things on his mind, mostly settled scores that need to be dredged up once again, to remind us was victorious. He takes on radio stations, a brave move that feels more like more corporate positioning than a personal vendetta. He works in one of his patented self-mythologizing personal history lessons, recounting a nearly fateful traffic stop with some gritty pulp lyricism. He steals material, as he always has, pinching the ‘strong arm a ho’ line from UGK’s “Touched,” not to mention the track’s entire chorus and title from an obscure Ice-T track. This feels less like theft than eminent domain, lyrical sampling from a man assured that everything is his for the taking. Basically, “99 Problems” is Jay-Z as we love him most: a powerful, entitled asshole with a backlog of experience and some imaginary crosses to bear. – Jesse Cataldo


“Show Me What You Got” from Kingdom Come (2006)

After announcing his retirement and releasing The Black Album, Jay-Z continued to work with a number of artists in various different formats-mostly as a producer, but also as a high-profile collaborator with Linkin Park. So it’s no surprise that Kingdom Come sounds like it was thrown together relatively quickly, rehashing a lot of the same old vibes but without the visceral punch behind it. Out of those dull ashes comes “Show Me What You Got,” a gloriously over-produced track that’s practically the polar opposite (both thematically and sonically) of his earlier recordings. The humble, street-raised rapper seems to have disappeared, making way for a more egotistical personality. He boasts about being the best rapper in the game (“Get the fuck out the throne you clone/ The King’s back“) and living the high life in Miami (“I’ll take you shopping/ Take long trips/ I’ll take the cork off/ You can take sips“). When Jay was a young rapper, it would have been easy to write off such arrogance as the aggression of a kid who went from rags to riches. Coming out of retirement though, with all the money in the world, the lyrics feel tired and vapid. When Jay isn’t beating a dead horse lyrically, “Show Me What You Got” boasts a solid bass line punctuated by a funky horn section. Sure, it’s often an overcrowded mess, but it’s a shiny, sparkling mess if there ever was one. Where “Minority Report,” a track that tackles the heavy subject matter of the governmental neglect of New Orleans post-Hurricane Katrina, shows great restraint and patience with melody, “Show Me What You Got” makes sure anything and everything sounds loud and furious. On an album of self-indulgent messes, there’s something to be said for a track that recognizes and defends the right to indulge so gleefully. – Kyle Fowle


“Roc Boys (And the Winner Is…)” from American Gangster (2007)

Even Rolling Stone can be right some of the time. After the muddle of Kingdom Come (2006), Jay-Z returned a year later with American Gangster, a collection of songs inspired by the Denzel Washington film of the same name. Although songs such as “Fallin'” and “Success” are among the most inspired of late ’00s Jay-Z, nothing can hold a candle to “Roc Boys (And the Winner Is…),” the song Rolling Stone called the best of 2007.

This is black superhero music,” Jay-Z shouts near the end of the song, and he ain’t kidding. Rapped over a Diddy production featuring an inspired sample from Daptone’s Menahan Street Band, Jay-Z shakes off the turgid Kingdom Come and busts out of the phone booth with his cape on. The sample may come from song called “Hit the Road by Walking,” but Jay and Diddy don’t give a fuck about walking, they come out flying.

Jay-Z is back in familiar territory, rapping about dealing drugs and evading the police. But “Roc Boys” and the rest of the songs on American Gangster do not have the autobiographical feel of much of Jay-Z’s earlier work. Instead, Hova is creating a character similar to Frank Lucas, the subject of the film. It’s as if Jay-Z needed to create a persona since the autobiography well had run dry. But seriously, by 2007 he was rich and famous. No one wants to hear another rap song about $1,000 meals and Beyonce Knowles. Jay-Z trusted his instinct and by using Frank Lucas as a model, wrote one of the most inspired albums, and songs, of his career. – David Harris


“Empire State of Mind (ft. Alicia Keys)” from The Blueprint III (2009)

Jay-Z has long had a love affair with his hometown of New York so there’s a certain justice to the fact that one of his biggest hits would be a hooky ode to Roc-A-Fella’s HQ. “Empire State of Mind” was tellingly Jay-Z’s first number one hit outside of appearances as a guest artist, as much a result of the song’s grafting of pop ingredients onto the Jay-Z template as it was perfect timing.

Because as much as “Empire State of Mind” is a chance for Jay-Z and Alicia Keys to celebrate their chosen city in their own way, it’s also an anthem for a time when hope for a better future is one of the only defenses against the brutally insistent feeling of doom permeating nearly every aspect of society. Jay-Z’s street eye view of the city that raised him gives the song its skeleton, his flow weaving like a taxi through the “Hard Knock Life (Ghetto Anthem)”-style pianos and bubbling bassline. Jay-Z’s encyclopedic knowledge of the New York streets and their ties to his career is infectious, specific and universal at once, tapping into the affection anyone can feel for their homes.

When the chorus hits and Keys shows off her impressive range, hitting notes that positively soar, it feels like victory, like all the cares in the world can go away if you just keep yourself focused on the good amongst the bad. Of course, that’s not at all how reality works but that’s the beauty of pop music, isn’t it? Its singular ability to make you forget your troubles through a melody you can’t stop humming and a beat that your feet can’t say no to. – Nick Hanover


“F.U.T.W.” from Magna Carta…Holy Grail (2013)

Magna Carta… Holy Grail is full of strained proclamations of greatness. Not all of them are as luxuriously straightforward as “F.U.T.W.,” however. With the steady pulse of one of producer Timbaland’s best beats in years, our vainglorious maestro works his magic even as he hedges into the ridiculous. This means an MC who sounds in control, even amid an album that so clearly identifies his waning skill and influence. The sense of creative collapse is as present here as anywhere else, but there’s something cohesively satisfying about this track, which lays out its statement of triumph neatly (confetti on his fur coat as he returns to Flatbush Ave. like a victorious emperor). Full of regal imagery and a laundry list of acquired goodies (from sports teams to wives and children), “F.U.T.W.” reveals he’s still pushing for more and always will be, its “no ceilings” reference both a nod to eternal ascendance and an admission that no amount of success will ever be enough for this constant striver.

This is paired with one of Jay’s more believable pleas for social justice, although it’s hard to take his call for revolution too seriously when it’s buried in a song whose title condenses its “Fuck Up This World” moniker down to a Walmart-safe acronym. The rapper still loves to play charitable, which means a running theme noting how nice it would be if everyone he left behind in Marcy could follow him up the ladder to success. But that magnanimity is also linked to a paradox. For all his crocodile tears about poverty and injustice, Jay loves the reality of a stratified capitalistic system that allows him to lord his success over everyone else. These contradictions have always been part of his persona, and the struggle between rootsy nostalgia and egotistical voracity provides a defined conflict that most of the other songs on this wooly album just can’t match. – Jesse Cataldo

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