Jay Z, like Che Guevara with bling on, is complex. That sentiment, expressed on “Public Service Announcement” (as well as by Jay’s look for his MTV Unplugged performance, where the face on his Che T-shirt was literally covered by his Roc chain), can be taken a lot of ways. But throughout his career, there have been at least two sides to Jay Z.
There’s the methodical craftsman and artist that’s seen the heaven and hell of the American Dream, who constructs technically air-tight raps stuffed with clever punchlines and astute social commentary that rarely places blame or settles for easy answers. Then there’s the ex-hustler, who courts pop stardom and isn’t above dropping a half-assed verse for a check (listen to him kill space on “Get This Money” by rapping about a bunch of different cranapple colored stuff, for example), because that Jay Z is still doing whatever he can to keep the pedal to the metal and never go back to where he came from.
But Jay would probably argue that his own duality is a commentary as well — the fact that poverty drove him to sell drugs in the first place and he still feels the impulse to do whatever he can to distance himself from that means something is wrong with America. And it’s the constantly shifting nature of these personas — the revolutionary, capitalist and revolutionary capitalist who’ll scream out “money ain’t a thing” then do a song with out-and-out Marxists dead prez — that makes Jay Z such a fascinating character.
Kanye and Jay Z © Kyle Gustafson
At this point, the Brooklyn rapper, who has won nearly two dozen Grammy Awards, has been around so long it’s easy to take him for granted. For many rap fans, there’s never been a world where Jay Z was anything but a monolithic figure within hip-hop, whose image and ideals functioned as shorthand for the very genre itself.
When it’s a given that you’re the best, though, people often don’t take the time to examine why you’re the best, especially when you’ve got a catalog as deep and varied as Hov’s. But we took the time and we did it. We took the liberty of assembling a list of Jay’s 20 best songs, so you never, ever forget that Jay Z is one of the greatest of all time.
1. “99 Problems”
Speaking of UGK, it’s Bun B’s part on “Touched” that Jay’s quoting in the third verse of this track. But seriously, this is the way you make your mark in hip-hop. Jay Z lured Rick Rubin, one of the genre’s original architects, back into the realm of rap production for a slamming beat that rivaled his work with LL Cool J or the Beastie Boys. Then there’s the track’s second verse, a narrative of racial profiling driving the cops to pull over a dealer who’s got something to hide, where Jay uses his smarts to pimp the system, killing time before the cops can call in the drug dogs. With Jay playing both himself and the cop, it’s as tense, pulpy and funny as a good crime novel.
2. “Big Pimpin'”
As both a rapper and a marketer, Jay Z’s always had a knack for collaborating with hot regional rappers, and helping bring them shine in New York while ingratiating himself on that artist’s turf. This has produced some great music, but none more classic than “Big Pimpin’,” Jay’s unrepentant lothario anthem featuring the Port Arther, Texas, luminaries UGK. This song is a classic for so many reasons — Jay’s flowing his ass off and UGK’s Bun B is in overdrive as he flosses with literary aplomb. But the true hero of the song is Bun’s partner Pimp C, who steals the show with an effortless eight-bar wonder in which he proves true playas don’t show; they show off. (There’s also the story of how Pimp’s obstinance threatened to derail the song in every way possible, but instead managed to elevate it to the canonical status it holds today.)
3. “Public Service Announcement”
Sometimes a song doesn’t need a hook when every bar is a hook in and of itself. That was the case in this iconic Black Album cut, where Jay Z’s meticulous verse construction aligned with his pop instincts to produce an anthem in which the listener hangs on his every word as Just Blaze’s anthemic beat propels you into the stratosphere.
It’s a given that in his prime, Jay Z possessed a competitive streak — you can almost hear him sweating trying to outdo rappers he perceives as competition on tracks like Cam’ron’s “Welcome to New York City” and the Ja Rule/DMX track “It’s Murda.” But that competitiveness was never more prominent than on “Takeover,” in which, over a Doors sample, Jay Z rips into Mobb Deep and dismantles Nas like he’s performing a mathematical proof, before shooing away the rest of the competition with the withering bon mot, “And for all you other cats throwing shots at Jigga / You only get half a bar: fuck y’all n****z.”
5. “Can’t Knock the Hustle”
The first track off Reasonable Doubt might just be the album’s best. It’s an absolute joy listening to Jay weave intricate rhymes oscillating between street talk and slick talk, such as the uncannily clever four-bar tennis metaphor that, if he ever heard it, probably made David Foster Wallace grin from ear to ear. Then there’s Mary J. Blige’s belted-out chorus, which sounded even better on Jay’s MTV Unplugged, when Jay brought her out to perform the track along with The Roots.
6. “Streets Is Watching”
Lots of rappers put essential truths into words through their rhymes, but few have done it with the frequency and acuity of Jay Z. The first half of this Vol. 1 track is Jay’s extended meditation of what’s essentially the rap game’s version of the founder’s dilemma: If I shoot you, I’m brainless, but if you shoot me, then you’re famous. Jay rounds the song out by detailing the exasperating minutia and abject paranoia of a life dedicated to the streets, mapping out his escape from the game in the process.
7. “Dear Summer”
Jay Z’s “retirement” from rap was less an actual retirement and more of an excuse to not drop an album for a couple years while he tried his hand at running Def Jam for a while. Hell, he hijacked an entire song on Memphis Bleek’s 534 album to ostensibly explain why he’d made the choice, only to spend half the track brushing off his enemies and dropping warnings to any pretenders to his throne. All of this, of course, was thrilling, like if Michael Jordan’s NBA Hall of Fame speech had come off as charming and endearing instead of perturbed and petty.
8. “Brooklyn’s Finest”
If we’re being honest, a list of the best Jay Z songs could just have been the tracklist of Reasonable Doubt. Songs like “Dead Presidents II,” “Can I Live,” “22 2’s,” “D’Evils” and “Friend or Foe” are all staggeringly good, but what really put Jay’s talent into perspective was watching him go bar for bar with his friend The Notorious B.I.G.
9. “A Million and One Questions / Rhyme No More”
Jay Z’s one of those perpetual, upwardly mobile underdogs: for him, every win means it’s time to take on another seemingly impossible challenge. He found himself in a weird position following his debut record Reasonable Doubt. The album had been widely hailed as a classic due to its rock-solid sound and Jay’s astonishing confidence and lyrical acumen, but Jay’s sales didn’t quite match up to the cred the album had won him. So the main question leading into Jay’s sophomore record Vol. 1… In My Lifetime was: could the numbers match up to Jay’s slick talk this time around? That big question, of course, came in the form of a bunch of little ones — a million and one to be exact — which Jay addressed then put to bed on this double dose of DJ Premier production.
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10. “1-900 Hustler” (Jay Z, Beanie Sigel, Freeway, Memphis Bleek)
This is probably the funniest — and perhaps weirdest — song in Jay Z’s catalog. It’s a concept song that finds Beanie Sigel running a 1-900 advice line for, uh, hustlers, directing calls to Jay, Memphis Bleek and Freeway. It’s hard to point out the most amazing moment — it’s a toss-up between Jay’s seemingly random aside of, “FYI, I’ve never been robbed in my life,” or when Beans puts a guy on hold, only to yell at him later in the song.
11. “Guess Who’s Back”
One of the undeniable highlights of Jay’s The Dynasty: Roc La Familia compilation was “This Can’t Be Life,” in which Jay, Roc-A-Fella signee Beanie Sigel and the Houston icon Scarface got so dark and deep that the Kanye-produced track nearly became a modern-day blues song. “Guess Who’s Back,” off Face’s late-period classic “The Fix,” is essentially that track’s inverse, in which those same key players celebrate the same streets they lamented on “This Can’t Be Life.”
12. “HOVA Song”
The intro to Vol. 3… The Life and Times of S. Carter seemed designed in a lab to make the listener feel unstoppable. This one-verse wonder contained more swaggering jewels than most other rappers’ entire albums.
13. “Money, Cash, Hoes” (feat. DMX)
If you were a rapper in the late ’90s and really wanted to spice your album up, you gave DMX a call. Swizz Beatz’s jarring keyboard arpeggios and blunt-force bassline helped the track feel like a nervy fight anthem, and as soon as you hear Dark Man X’s signature growl on the intro to this Vol. 2… Hard Knock Life single, you knew Jay was about to kick things up a notch.
14. “Heart of the City”
Perhaps Jay’s most definitive artistic statement was The Blueprint, the 2001 album in which Jay went from a force in the rap game to a one-man movement. Everyone always remembers the pop smash “Izzo” and the acidic “Takeover,” but the album’s true apotheosis was “Heart of the City,” where Jay lays his case out plainly for why he’s the best around.
Jay-Z performs at the Ziggo Dome © Greetsia Tent / Getty Images
15. “Young, Gifted and Black”
One of the instrumentals Jay Z tackled on his S. Carter Collection mixtape was Big Daddy Kane’s “Young, Gifted and Black.” Jay renders the song’s title an ironic joke, as he holds the privilege of the white world in one hand while showing the poverty of the hood in the other, rapping, “Y’all must really be in heaven there, somebody tell God we got a couple questions here.”
Part of what’s so great about Jay Z is his ability to make technical and lyrical brilliance sound effortless. Which is why sometimes, it’s just sublimely fun to hear Jay Z talk some smack. And that’s exactly what he did on “Threat,” over a beat the North Carolina producer 9th Wonder made in 20 minutes, featuring faux-menacing yowls from Cedric the Entertainer and culminating in one of Jay’s most flagrant threats ever: “I will kill you, commit suicide and kill you again.”
17. “The Joy” (The Throne feat. Pete Rock)
Kanye West and Jay Z’s “The Joy,” which originally surfaced as part of Yeezy’s G.O.O.D. Fridays series was an event in the same way that a long-overdue reunion with a family member is an event. The track was the first time Jay linked with his fellow New York rap veteran Pete Rock and while Kanye’s verse oscillates between goofy sex jokes and self-empowerment aphorisms, Jay treats Rock’s Curtis Mayfield flip with reverence, rapping about his childhood with a mix of nostalgia and regret.
18. “Go Crazy” (Young Jeezy feat. Jay Z)
By the mid-2000s, Jay Z was ostensibly retired and his guest verses were few and far between. But he couldn’t help but go all out on Young Jeezy’s “Go Crazy,” riding Don Cannon’s impeccable soul loop to self-canonize, tracing his route from the trap to the top.
19. “Stretch & Bobbito Freestyle” (with Big L)
“If you wanna put your man on too you can do it together,” the legendary radio personality and DJ Bobbito Garcia told Big L on air after he showed up to the Stretch and Bobbito show with his friend Jay Z in tow. After kicking a blistering freestyle, L encourages his homie to hit the mic. The then-unknown Jay slides into the beat with a double-timed flow that nevertheless showcased Jay’s incredible comfort on the mic. He and L trade verses for nine minutes, delivering such a striking tag-team performance that when Jay listened back to the freestyle for “Stretch and Bobbito: Radio that Changed Lives” documentary, even he couldn’t help but be impressed.
It’s a common assertion that Jay Z’s lost a step in his later years and it’s true that his latter-day solo efforts, such as “Magna Carta Holy Grail” and “Kingdom Come,” don’t quite live up to his classics. But in 2016, Hova dropped one of the most politically charged tracks of his career, a response to the deaths of Alton Sterling and Philando Castile at the hands of police, addressing the cycles of poverty and racial profiling that are endemic to the Black community.
Read more: The 100 Greatest Songs of All Time