Photo: Joella Marano, CC BY-SA 2.0 , via Wikimedia Commons

The 20 Best Jay-Z Songs

Jay-Z has set himself apart in hip-hop by making forward-looking, awe-inspiring, never-been-done-before revelatory choices. These are his best songs.

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 ’90s 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, 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.