To try and nail down a list of the best Jay-Z songs is kind of like trying to nail down a list of Michael Jordan’s best moments on a basketball court. Moments — not dunks, not passes, not shots, not highlights — moments. Because, much like his roundball peer, the man born Shawn Carter has built his empire not merely by showcasing his exceptional rhyming skills. Rather, he has set himself apart by making forward-looking, awe-inspiring, never-been-done-before, revelatory choices that have helped lead a personalized sense of transcendence throughout all of hip-hop.
Jay-Z was the first rapper to age gracefully, the one who embraced preconceived ageism within a subculture by confronting it head-on, proclaiming “30 was the new 20” without anyone even remotely challenging him. He took one of the most electrifying beefs the medium has ever seen (with Nas) and turned it into a lucrative business proposition, proving first-hand that it can be wise to swallow our pride every now and then. To top it all off, he developed a sports agency, signing some of the most celebrated athletes of American sports at breakneck speed, reminding us all that his mind wanders far beyond the realm of simple beats and complicated words.
But, alas, such is why we are here in the first place: To try and contain an idiom that frankly can’t possibly be defined; to try and nail down a best-of list when it comes to the output Jay-Z has so graciously offered over the years. Some of these tracks will be predictable; others may force you to scratch your head. Some will be scoffed at; others will be imperative. A list like this is so hard when greatness comes this easily to a single artist, and while this particular collection will highlight only 20 of his songs, it would undoubtedly be just as easy to pick another group of entirely different tracks to debate alongside the following picks.
“They say they never really miss you ’till you’re dead or you’re gone,” Mr. Carter raps on his Black Album highlight (which didn’t even make this list) “December 4th”. Behold one man’s inevitably ill-fated shot at trying to categorize the Brooklyn rapper’s best 20 moments throughout his solo studio career, excluding mixtapes, live records, and guest appearances, of course (because as we should know by now, factoring in those moments could take someone a full life to conclude).
Unlike his basketball equal, Hov never needed to dunk on anyone to make his point. Consider the following 20 tracks enough reason to accept that when you’re this good, taking flight means far more than merely leaving the ground.
20. “Roc Boys (And the Winner Is….)” (American Gangster, 2007)
Sure, it’s easy to sleep on this song, coming from 2007’s (non) soundtrack to the Denzel Washington/Russell Crowe flick American Gangster, but as soon as the first few notes of that horn refrain blast through the speakers, it becomes harder and harder to dispute its title as Best Forgotten Single of Jay’s catalog. Better yet is Kanye West’s vague guest utterances that sit in the background as well placed as the perfect houseplant in a temple built for emperors. Most memorable moment? Mr. Carter actually takes time to thank us, the customers, at the end of the track’s first verse. We all knew he was a master lyricist, but who knew Hov could also be so accommodating?
19. “Song Cry” (The Blueprint, 2001)
If you have to pick a ballad, this has to be the choice, right? The rapper’s tale of a strong love lost and a good girl who’s gone bad is mesmerizing in its poignancy. Gone is the braggadocio that appears on the rest of The Blueprint (the album on which this standout track appears) and present is a string of words reportedly inspired by not one, but three different relationships Jay had been through earlier in his life. It’s hard to be affecting, sentimental, and reflective in the world of hip-hop — especially in 2001, when this track was released as a single — but here, Hov manages to utilize all those elements, making it cool to wear your heart on your sleeve, even if your parents are sagging low.
18. “30 Something” (Kingdom Come, 2006)
Not a song typically seen on these kinds of lists, the case for “30 Something” goes like this: Jay-Z has been the first rapper in the medium to successfully grow old in front of our eyes, all while maintaining an increased relevance within popular culture. With that in mind, this track, from his slightly subpar Kingdom Come, marked a flashpoint in his maturation, single-handedly quelling preconceived prejudices against age in rap music. Maybe it’s not his most clever. Maybe it doesn’t have the hottest beat. And maybe in spots, it can even sound a bit corny. Still, you can’t deny this: Mr. Carter was the first one to come around and make growing old (not up) acceptable, if not celebrated. Like it or not, “30 Something” had a lot to do with that.
17. “Can’t Knock the Hustle” (Reasonable Doubt, 1996)
“Yo I’m making short-term goals when the weather folds / Just put away the leathers and put ice on the gold / Chilly with enough bail money to free a big willie / High stakes, I got more at steak than Philly.” Whoa … what?! Jay-Z’s de facto introduction to the world (this being track one on Reasonable Doubt, remember), “Can’t Knock the Hustle” is as smooth as milk chocolate and as defiant as six Kanye Wests. Mary J. Blige stops by for a more-soulful-than-you-think chorus, and as anyone who has seen this performed live with both artists on stage can tell you, the intangible chemistry between the two is a lesson in collaboration. It’s not possible to have a better first song on a first album. Actually, it’s probably not even fair.
16. “No Hook” (American Gangster, 2007)
All right, all right. So, maybe this is a tough one to buy into, but there’s something about the way he slows down his flow in the song’s second verse as he recites “But I got to get you out of here momma or I’m gonna … die … inside … and either you lose me momma so let loose of me”. A lost track from his lost album, “No Hook” works on so many levels: Storytelling (“Poor me, dad was gone, finally got my dad back / Liver bad, he wouldn’t live long, they snatched my dad back”); audacity (“Fuck rich let’s get wealthy who else gonna feed we / If I need it I’m gonna get it, however, God help me”); and approach (the whole thing barely eclipses the three-minute mark, yet not once does it suffer from a lack of a chorus). Yes, he didn’t need any hook for that shit.
“Heart of the City (Ain’t No Love)” (The Blueprint, 2001)
Cop the MTV Unplugged version if you get the chance — hearing the Roots switch grooves and melodies behind Jay is a lesson in musicality, and Jaguar Wright’s backing vocals are absolutely electric. Its original incarnation was a hit for Bobby Bland in 1974, and the core of it has been covered approximately seven trillion times by everyone from the Allman Brothers to Paul Carrack. Still, it’s this take, dreamed up by an unknown Kanye West, that has made its way into movie trailers and car commercials these days. Maybe the most soulful he has ever been on record, Jay spits with purpose here, confronting all his haters and silencing his harshest critics. If this doesn’t make your legs move and your torso gyrate, you’re going to have to call a doctor. No way in hell you have a pulse.
“I heard motherfuckers saying they made Hov / Made Hov say, ‘OK so, make another Hov’.” Granted, this might be a little high for a virtually ignored single that came from a virtually ignored comeback album, but just remember that all the way back in 2006, when this song was first released, nobody — nobody — had any insight into whatever the hell was going on between Jay-Z and Beyonce. Enter verse two, stage right. For as biting and anthemic as his now wife’s “Irreplaceable” was, this was every bit as subliminal in its confrontation. Bookend it with a verse about doubters and another about his deceased nephew, add a chorus from an at-the-time-anomaly, Chrisette Michele, along with some piano from Dr. Dre, and you have the formula for, as Jay himself put it, “not a diss song, just a real song, you know?” We certainly do.
13. “D’evils” (Reasonable Doubt, 1996)
From the title on down to the final line — “And even if Jehovah witness, bet he’ll never testify” — this deep Reasonable Doubt cut is one of a handful of coming-out wordplay parties that appear on Hov’s classic debut LP. With a little help from Snoop Dogg, the track meshes an eclectic smorgasbord of samples, all the way from Allen Toussaint’s “Go Back Home” to an old LL Cool J remix. The result, as one may imagine, is unforgettable in breadth and transcendent in execution. Working as one, big confessional, the track proved to be a clear indicator of how deep Mr. Carter could delve based entirely on his intellect alone. There is a reason why that 1996 record will forever be etched into hip-hop history as one of its best. “D’evils” is a big part of it.
12. “The Watcher 2” (The Blueprint 2, 2002)
Who says The Blueprint 2 was a disaster?! The sequel to Dr. Dre’s song of the same name, Jay-Z kills his verse so thoroughly that a lawyer should have brought charges against him for first-degree murder. Sure, the follow-up to the rapper’s second classic full-length wasn’t the critical or commercial success he may have wanted it to be, but that doesn’t mean that there weren’t any gems throughout any of the two CDs this release offered. “You n– ain’t know how to floss ’til I came through the door”, Hov utters during his extended first verse. “Like ‘Eric B. for Pres’, respect me in this BITCH!” What makes that the best part? Check out the track’s final third and listen as … you guessed it … Rakim steps up. A gem indeed.
11. “D.O.A. (Death of Auto Tune)” (The Blueprint 3, 2009)
This brought the man his eighth Grammy, and it’s clear why: not since Bob Dylan went electric did a guy successfully confront a stylistic trend with so much vigor and expertise that the populous’ opinion about a single medium was seemingly changed overnight. He took a little flak for it, but no matter — this was Jay-Z, remember, the one rap artist white people actually listen to consistently. No I.D.’s raw production plays perfectly into the declaration of war this tune ultimately proves to be, and Mr. Carter is, as always, up to the task. “Get back to rap, you’re T-Pain’n too much”, he utters, almost instantaneously wrecking a best-selling music artist’s career. When reached for comment, Mr. Pain ignored the question and simply asked if we would be interested in signing up for a Best Buy card.
10. “Where I’m From” (In My Lifetime Vol. 1, 1997)
It’s the ultimate hometown anthem, the song any fan from almost any walk of life can relate to, if only for how fundamentally proud people are about wherever it is their roots remain. For Jay-Z, the story painted a bitter picture of inner-city life, his words serving as a comment from the ignored about the ignored. “I’m from the place where the church is the flakiest / And n– is praying to god so long that they Atheist / Where you can’t put your vest away and say you’ll wear it tomorrow / Cause the day after we’ll be saying, damn I was just with him yesterday”, he proclaims during the song’s second verse. Back it up with some moody, bare-boned production, and what you have is nothing less than a late 1990s classic piece of hip-hop.
9. “Venus Vs. Mars” (The Blueprint 3, 2009)
Say what you want about contemporary Jay-Z songs (and say even more about the contemporary Jay-Z songs that aren’t singles), but the one thing you can’t deny is how overtly clever this particular narrative is between a man a woman gets with each listen. Literally — and yes, in this case, “literally” actually means “literally” — every two lines reveal a new punchline, a new play on words, a new observation, a new pay-off. Listening to it is like watching an episode of Ugly Betty: You sit on the edge of your seat to see what’s next, to see how the brand new twist will lead to the inevitable brand-brand new twist. “Whether black or white / We both like Mike / We both like Jordans / We both Phil’s Knights,” Hov asserts. Oh, just stop it.
8. “Ni**a What, Ni**a Who (Originator 99)” (Vol. 2: Hard Knock Life, 1998)
It’s that flow. It’s that nasty, lightning-quick, don’t-blink-or-you’ll-miss-it, butter-smooth flow. It’s that ease with which the man born Shawn Carter glides through such a complicated, funk-filled groove. It’s that … it’s that shit. Coming from Vol. 2: Hard Knock Life, this track is as technically impressive as anything the guy has put on wax, and it single-handedly makes the case for the marriage between Timbaland and Jay-Z as a union impossible to discount and imperative to maintain. If nothing else, this might be the most memorable moment Amil will ever have on a record, as her faded choruses provide attitude and character behind the whip-smart words Jay strings together. A lot of people tend to forget how versatile the rapper can be whenever he decides to switch things up. This song should forever serve as a reminder for those doubters.
7. “What More Can I Say” (The Black Album, 2003)
If the Gladiator sample doesn’t get you, then the final a cappella refrain most certainly will. From Jay-Z’s first attempt at retirement, The Black Album, this standout track provides the record’s most earnest throw-the-mic-down-and-walk-away moment. T.I. liked it so much that he eventually turned one of its lines into a hit of his own. Danger Mouse liked it so much, he matched it with the Beatles’ “While My Guitar Gently Weeps” on his Fab Four/Jay-Z mashup, The Grey Album. And the rapper himself liked it so much that he made it one of the most electric and standout moments on his (not really) swan-song concert movie, Fade to Black. The man said it himself: he’s supposed to be No. 1 on everybody’s list. This track proves it.
6. “Empire State of Mind” (The Blueprint 3, 2009)
Jay-Z’s first No. 1 single as a lead artist on Billboard‘s Hot 100. It’s certifiably insane to think that it took him almost 15 years, isn’t it? Alicia Keys’ voice soars through the city night as Hov offers up his typical wit and, in this case, New York authenticity. All told, the song became the unofficial anthem of the most celebrated city in the world, quite the feat for a guy who didn’t even pick up a mic until he reached adulthood. The LeBron/Dwayne Wade line turned heads everywhere, but it’s that third verse that truly allows Jay to spread his wings: “Caught up in the in-crowd, now you’re in style / And in the winter gets cold, in Vogue with your skin out,” he says as the music begins to rise. The world’s greatest city. The world’s greatest rapper. It only makes sense.
5. “Moment of Clarity” (The Black Album, 2003)
This is the one that nobody wants to think about when these lists pop up. A relatively unknown track off The Black Album, this Eminem-produced confessional is easily one of the most impressive tomes in the rapper’s lengthy library. Just check the hook: “Thank God for granting me / This moment of clarity / This moment of honesty / The world’ll feel my truths / Through my hard knock life time / My gift and the curse / I gave you volume after volume of my work / So you can feel my truths / I built the Dynasty by being one of the realest n—s out / Way beyond a reasonable doubt / From my blueprint beginnings / To that black album ending / Listen close you hear what I’m about / N— feel my truths”.
See what he did there? Oh, wait. You’re still not sold? How about this: “If skills sold / Truth be told / I’d probably be / Lyrically / Talib Kweli / Truthfully / I wanna rhyme like Common Sense (But I did five Mil) / I ain’t been rhyming like Common since / When your sense got that much in common / And you been hosteling since / Your inception / Fuck perception / Go with what makes sense / Since I know what I’m up against / We as rappers must decide what’s most important.” The defense rests.
4. “Takeover” (The Blueprint, 2001)
Quite possibly the most hostile Jay-Z has ever been on one of his own albums, “Takeover” is a class in retribution without anybody even asking Hov if he had bothered trying to obtain a teaching certificate. Set to the Doors’ “Five to One”, this Blueprint standout caused waves in hip-hop circles everywhere as the beef between Nas and Jay went from “Hot” to “Torching”. A lot of people still claim that “Ether” is the superior of the tracks traded between the two artists, though lest we be reminded that it was Mr. Carter who fired the first on-an-official-record shot in this war of words, and sometimes being the originator can warrant a few bonus points for balls.
Also, Nasir wasn’t Jay’s only target here, remember, as the Brooklyn native famously devoted a portion of his words to Mobb Deep and “all you other cats throwin’ shots at Jigga” right before that final half-bar became the single most affecting half-bar in the history of rap music. Enthusiasts can debate who won the battle for centuries to come, but if nothing else, the “Takeover” proved this: it’s unwise to fuck with Jay-Z.
3. “Brooklyn’s Finest” (Reasonable Doubt, 1996)
To think that Jay-Z has been around long enough to warrant a real, in-the-flesh collaboration with B.I.G. is a testament to both his influence and his durability. Here, the two greatest wordsmiths any of the five boroughs have ever cultivated go back and forth like two life-long friends conversing on a back porch somewhere in the middle of Kansas. Hov leans on B.I.G., the much more recognizable and popular name at the time, but listening to it 15 years after the fact will reveal a newfound appreciation for how well the dueling giants worked with one another.
You thought Jay would have had him during the track’s latter half when it spits, “For nine six, the only MC with a flu / Yeah I rhyme sick, I be what you’re tryin to do / Made a fortune off Peru, extradite, china white heron / N– please, like short sleeves I bear arms / Stay out my way from here on”. Au contraire, Mr. Wallace noted as he responded, “Me and Gutter had two spots / The two for five dollar hits, the blue tops / Gotta go, Coolio mean it’s gettin’ too hot / If Fay had twins, she’d probably have two Pac’s / Get it? Tu-pac’s.” The teacher gone too soon schooling a student who would become a master. Priceless.
2. “Hard Knock Life (Ghetto Anthem)” (Vol. 2: Hard Knock Life, 1998)
People can argue until they are blue in the face about how much impact Jay-Z has had on the hip-hop industry. Some can say other rappers are more technically sound, wittier, or more clever. Others can make the case that he’s sold out, that he’s a shell of himself, that he’s gone pop, or that he’s not nearly as imperative to the fabric of the rap game as some people believe. That’s fine, of course. But all those people would be outlandishly wrong and this transcendent, brilliantly constructed single submersed in subversion is Exhibit A when considering precisely how wrong those blow-hards would be.
There’s not much to it — just a simple beat that crawls along like a turtle wearing an oversized white T. The guy has certainly offered more intellectual rhymes before, opting here for overtly accessible short verses and a chorus ripped off directly from Annie, as we all know by now. But — and this is important but — the message behind this tiny, little four-minute ditty took an entire subculture that had been bubbling on the streets of inner-city America for decades and threw it in the faces of people who insisted the medium never had a future.
The song wasn’t a statement any more than it was a white flag — an admission that everybody on the streets knew how much they were being ignored and everybody on the streets were heretofore content with just sitting back and watching as the circle of drugs, crime, corruption, and every other ugly thing this world offers continued while the tune of voices barely old enough to know right from wrong filled the air.
The song is underestimated in its relevance and outright neglected in its intellect. Jay-Z set himself apart here, standing in front of popular culture and displaying one gigantic wink, informing everyone else that his vision reaches far beyond bitches and blunts. It would be the single most telling moment within an artist eager to explore and quick to evolve. “Hip-hop has to thank God for Jay-Z”, Nas once said. And this song proves why.
1. “Renegade” (The Blueprint, 2001)
All right. Here it is. Predictable as it may be, you would be hard-pressed to find a heavier collaboration in hip-hop over the course of the last decade-and-a-half. Some claim Eminem got at Jay-Z on this one, but those who believe as much aren’t listening. “See”, Jay began, “I’m influenced by the ghetto you ruined / That same dude you gave nothing, I made something doing / What I do, through and through and / I gave you the news with a twist / It’s just his ghetto point of view / The renegade you been afraid / I penetrate pop culture / Bring ’em a lot closer to the block where they / Pop toasters and they live with they moms / Got dropped roasters, from botched robberies n– crotched over / Knocked down by some clown when child support knocked / No, he’s not around / Now how that sound to ya, jot it down / I’ll bring you through the ghetto without riding round / Hiding down ducking strays from frustrated youths stuck in their ways / Just read a magazine that fucked up my day.”
If “Hard Knock Life (Ghetto Anthem)” was Mr. Carter’s 63-point game against the 1985-86 Boston Celtics in the early rounds of the playoffs, “Renegade” was his title-winning series against the 1990-91 Lakers, the moment when he could look back on what he had achieved to that point in his career and essentially say the following to everyone who doubted him: “I told you so.” Pieced together over a menacing beat that instantly sets a palpably defiant tone, “Renegade” is an all-time classic not just in Jay-Z’s catalog, but in the entire song list of hip-hop’s history.
He had hits before it. He had sold millions of records. Shoot, he was rich, if not wealthy, by the time both the song and the album hit the streets. He had credibility. He had a loyal fan base. He had won awards. He had established himself as a major player. And to think, this was all in … 2001. Again: 2001. Since then, he’s gone on to become the elder statesmen within a genre of music that has almost completely taken over contemporary popular music. The assurance and iconic status of “Renegade” have helped him earn his place among the most important figures in hip-hop. This song didn’t announce his arrival at the party — it merely announced the fact that he had no plans to leave.
This article was originally published on 2 July 2013.