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 by merely 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 as much. 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 easy 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.