Jay-Z’s Top 51 Songs to a Hip-Hop Head Pt. I

Being that Jay-Z turns 51 today, I thought this would be a good opportunity to revisit and review his catalogue.

I realize that others have taken a crack at ranking Jay’s songs and all come at it from different angles. I’m not a music critic, but I’ve been a hip hop head from the second I heard rap for the first time. I wasn’t just interested in the beat or the lyrics. I wanted to know who produced the song and what the meaning was behind every line.

With that intense dedication to rap, I consumed everything about hip hop, and rap in particular, at a maniacal volume. From 1997 to 2009 I knew everything there was about rap — commercial, underground, or otherwise. And when Biggie and Tupac tragically were no longer releasing new music due to their untimely deaths, Jay-Z and Nas bore the brunt of my attention.

I really became aware of Jay-Z from Foxy Brown’s I’ll Be single. I used to religiously cycle through MTV, BET, and The Box channels (side note, my family couldn’t afford much during my youth, but we had cable, which turned out to be a beautiful escape. Shout out to my parents for getting us cable.) and one day Foxy’s song came on. I loved the beat, the video, and her raps but I thought the dude on the song was a huge nerd. That dude turned out to be one Jay-Z.

Jay looked out of place. The glasses weren’t working the fit (please find any other music video where he’s wearing what amounts to yellow-tinted reading glasses) and he was so low energy. But the song worked. To me, the song worked because of Foxy, not Jay. So I was shocked when Volume 2 dropped. It was an instant classic that should’ve been a 5 mic album (iykyk), and from that album on I consumed every Jay-Z song, including his back catalogue.

Some methodology on my rankings:

I am considering his entire solo discography (Reasonable Doubt to 4:44) and Watch The Throne. I won’t be including the two albums he did with R. Kelly nor Everything is Love, his collaboration with Beyonce. Mainly, because I don’t want to talk about R. Kelly and because I find that Everything is Love is really a Beyonce album heavily featuring Jay-Z. That’s how I feel don’t @ me.

I won’t consider live albums for the same reason as collab albums, nor am I considering full soundtracks or mixtapes, but I am considering singles he may have recorded for a soundtrack (Brooklyn We Go Hard). Though, I am considering songs Jay-Z is featured on as a co-artist or the main artist under someone else’s name. Meaning, I will consider songs like Ruff Ryder’s Jigga My N**** which is basically a Jay-Z song by Ruff Ryders. Same goes for solo sounding Jay-Z songs released by DJ Khaled.

There may be some unreleased or non-album songs here and there that I might throw in, like Super Ugly. That might make the list.

In terms of what I’m considering about each specific song, I am basing my rankings off of:

1. Cultural Significance — how deeply was hip hop culture affected
2. Lyrical Significance — what did Jay do linguistically that set the song apart
3. Personal Significance — both to Jay-Z and me. Meaning, what was of significance in Jay-Z’s life to lead him to record the song and why was that important, and what was going on in my life that it affected me due to what he said.

*WHEW* Ok, that was a lot to get through just to get to the list, so let’s do this. (I might also break this out into multiple parts if it gets too long).

50. Who You Wit II

If there is a starting point for the artistic development arc of an artist like Jay-Z, there is no more perfect starting point than this song. From the opening lines about bitches, he spends the rest of this song establishing his reputation as the clique to be with. The means of dominance? Money and women. Even though this song was off his sophomore effort, you can hear traces of the rapid-fire style flow that was his calling card as an up and coming emcee. The music video for this song revolves around a lavish ball thrown in honor of the “Player of the Year” award, which Jay wins. A theme that would be frequented throughout many albums in his career.

49. Jigga My N***a

Few Jay songs have a more sinister, ominous, dangerous, and hype intro than this. Produced by Swizz Beatz for the Ruff Ryders’ Ryde or Die Vol. 1 compilation album, your ears are blasted in the opening notes by slow and ominous horns that make you feel like something epic is about to happen. The drums are on beat with the horns so it thumps your chest, too. The beat quickens and Jay-Z says “lights out n****s”, the beat drops and you lose your mind. I found myself at a house party in Miami at 2 in the morning when the intro to this song came on. The room was dark, smoke was thick, the girls stopped dancing, dudes stood still. Then, at the top of our lungs and in unison with Jay we ordered the lights out, girls took care of chanting “JIGGA” and dudes demanded we be told what our M****r F*****g names were. We rapped every word, very much in our own music video.

48. The City is Mine ft. Blackstreet

A single off the subpar In My Lifetime Vol. 1, the reason this song clocks into the list is because while it wasn’t a major commercial success, Jay-Z lay claim to the throne as New York City’s king following Biggie’s passing. At the time, few people outside of Roc-a-Fella felt this way when there were so many other emcees that could also be heir-apparent, especially someone like Nas. Jay-Z’s flow had grown in confidence and shed the gimmicky speed of his earlier efforts, but is still audibly different than how the mainstream came to know him.

47. Supaugly

Probably the most vicious record in Jay-Z’s repertoire, this song was in response to Nas’ Ether, which was widely seen as the deathblow to Jay in his beef with Nas. In the wake of Tupac and Biggie’s tragic beef, Super Ugly was seen as the escalation point of no return. So high were the stakes that Jay’s own mother publicly rebuked her grown adult son for the things he said about Nas on the record. There were one or two more volleys in the rap battle, but there’s no coming back from your own mother telling you that you went too far. Despite Jay taking the L in this instance, he would ultimately overcome it to achieve successes in ways Nas never could.

46. Run This Town ft. Rihanna and Kanye West

Upon initial listen, you might not be impressed, but this was a Grammy winning commercial success for Jay-Z. Off The Blueprint 3, and following the “old-head” Death of Autotune single, Run This Town felt anthemic with its sing-along friendly Rihanna-led chorus. You felt badass when you rapped along Jay’s

Get your fatigues on, all black everything, Black cards, black cars, all black everything.

Been driving a black car ever since then.

45. Can’t Knock The Hustle ft. Mary J. Blige

The third single off his classic debut from 1996, Reasonable Doubt, having Mary J. Blige on this song was a major win for the then unknown Jay-Z. This song isn’t really what I gravitate toward in Jay’s discography, but it was an important song in his career in terms of establishing cred with a bonafide star hopping on the song. Jay-Z has said in interviews that at a time in his life he referred to his work on the streets as his full time job and rapping as his hustle. Many people originally thought he was referring to his hustle the other way around, which is a testament to Jay’s mastery of the double entendre since the beginning of his career.

44. Lucifer

Not a single, but part of his critically acclaimed and commercially successful The Black Album, Lucifer’s opening piano notes feel like you’re going to ease into the song but then get immediately punched by the beat and reggae sample screaming “Lucifer, Lucifer, son of the morning! I’m gonna chase you out of Earth.” Jay deftly leans into the religious themes, opening the first verse by asking for forgiveness for his righteous cause for sinning: mainly, murdering his competition. But, surprisingly, Jay uses the last verse to mourn the murder of a friend, and confesses to the Lord that the desire for revenge in his heart can be blamed on the son of the morning. Not the type of vulnerable look people would think comes from Jay.

43. Ride or Die

A criminally underrated and overlooked cut on the classic Vol. 2…Hard Knock Life. Not only does Jay give a swagger masterclass, but also one in poetry and linguistic gymnastics when he opens the song by employing a little known, but commonly used, figure of speech called epistrophe (the ending of a series of lines, phrases, clauses, or sentences with the same word or words). With the beauty of rap’s poetry in full display, Jay ends the opening verse with more epistrophe:

niggas cat fighting with Jigga, kicking sneaky shit
making little takes but keeping it a secret
’cause I kick that deep shit
that divide your peeps shit
now I don’t know if you f*cking with Jigga
spittin’ that weak shit

(one more note on epistrophe: probably the most popular and best known use of it is Juvenile’s Ha, off 400 Degreez, and whose Remix Jay-Z is on)

42. Excuse Me Miss

One of the only two songs worth listening to from his wildly forgettable double disc The Blueprint 2: The Gift and The Curse. (the other song from this album is also on this list, further down, surprisingly) What’s notable about Excuse Me Miss is Jay’s pivot to a more “grown” persona, interested not just expensive things, but a luxurious lifestyle. And, more shockingly, monogamy — one of the least popular themes across all rap. But this evolution is uncommon among rappers and a key to Jay’s longevity. Most rappers fade into irrelevance as they age because their music’s subject matter ceases to match their lives’ reality, which Jay was able to avoid by not shying away from doing.

41. Change Clothes

The Black Album immediately followed The Blueprint 2, so it’s no surprise that we continue to see Jay’s image evolve from mere street hustler, to boss, to magnate. Change Clothes is a straightforward declaration that the street hustler Jay is in the past, suited and grown Jay is the present and future. In this, he further separated himself from the competition who was not achieving success in ways that he was, and therefore was not able to compete with him at the top.

40. Hell Yeah (Pimp the System) Remix

This is not a Jay-Z original. He’s the featured guest artist on a song by the militant rap duo Dead Prez. Not really well known, Dead Prez’s raps advocated for some extreme views that weren’t commercially viable, but on this song, they pulled back the curtain on some criminal activities that happen out of desperation for survival. Reminds me of Tupac’s line from Changes where he says he’s never committed a crime he ain’t have to do. The song was released in early 2004, but Jay’s verse can easily speak to what’s going on in 2020. In his verse, he raps about how when he was actually selling drugs he never saw cops, but now that he slings raps to kids and has moved to the suburbs, he gets harassed because parents are nervous that their kids want to look and sound like him. As he describes cops coming to beat him, he asks “who you smacking on, I’m only trying to eat what you snacking on.”

39. Numb/Encore

I’m including the Linkin Park mashup version for one reason and one reason only: The Black Album version of Encore is corny. And there are few things I hate more than corniness, ask my wife. The beat doesn’t match Jay’s energy, it feels childish and just plain wack. I wasn’t a fan of it when the original version first came out, and I definitely can’t stand it now. But when you juxtapose Jay’s lyrics delineating his triumphs and successes over Linkin Park’s beat of a song about wanting to escape the pressure of misplaced expectations, you get a more deeply meaningful song. In a way, it acts like a letter from a future self to the younger self, that they were able to escape the feelings of being a loser in someone’s eyes because they bet on themselves and succeeded. As an adult, this hits different, because I’d love to tell 14 year old me that the feeling he’s feeling will be but a distant memory at 38.

38. I Know

The first entry on this list from his American Gangster album, this single brings the movie and album’s concept full circle. The album was inspired by the movie of the same name, which told the story of Frank Lucas, a heroin dealer. I Know is a multi-layered metaphor for heroine in which he takes on three different personas of user, dealer, and the drug itself. While many metaphorical songs exist in the vaults of hip hop (two standouts are Common’s I Used to Love H.E.R. and Tupac’s Me and My Girlfriend), the ease with which Jay ties all the concepts together (movie, album, song) is a flex.

37. Pray

Another track off American Gangster, in Pray, Jay turns the director’s lens on himself and gives the listener a look into what made him who he is. Describing different scenarios, each perilous in their own way, Jay turns toward prayer each time. Again, he conceptually ties the movie’s subject to his music but from his own narrative and experience, given that he was also a drug dealer. On canvas, this song would be a self-portrait hanging on a museum wall.

36. On To The Next

Inspirational as the message of dusting yourself off and moving on to the next one, it’s also a critique of the rumblings from fans and critics that Jay-Z’s work should be more like Reasonable Doubt and his earlier work rather than forward-looking. In a culture that praises those that “keep it real” (read: don’t evolve from a street mentality), Jay wasn’t afraid to buck the status quo.

35. American Dreamin’

The American Dream, a pillar of American Lore. The United States is seen by many as the land of opportunity, where dreams can be achieved by pulling oneself by the boot straps and working hard. Every American Dream starts with the same end in mind: Success. But not every path looks the same. If the standard American Dream’s self-made path is paved with hard work, there is the Upside Down version of the American Dream, a path paved with perilous pitfalls that lure victims with promises of quick riches but at the cost of many lives. American Dreamin’ is the darker, more sinister look at the American Dream delivered in a way that only Jay can.

34. December 4th

I’m gonna be upfront about this: I strongly dislike the production of this song. I find it corny, just like Encore’s. But, despite most of Jay’s body of work giving you glimpses into his life, one of the reasons this song stands out from other autobiographical songs is the inclusion of his mother on the track. The revealing content of the verses are also much more personal. Rap’s greatest myth is that rappers are honest about what they rap. So when a rapper is actually honest, it’s a bit shocking, especially when it comes from the rapper at the top of his game.

33. (Always Be My) Sunshine

A duet with Foxy Brown from his sophomore effort, you might be surprised to see an entry from that album this high. But, as the first single since Reasonable Doubt, this song marked a difference between newcomer Jay and more established Jay. As an up and coming rapper, Jay-Z paid his dues under the tutelage of one Jaz-O (if the nome the plume similarities didn’t give it away), whose calling card was a machine gun fast flow and penchant for cramming as many rhyming syllables as possible into every bar. Take a listen to The Originators to have your head spin. But then listen to Sunshine to hear how his flow had grown from gimmicky to respectable. Also, Babyface sang the hook. One of the few times you can find the LA Face label co-founder on a rap track.

32. Money, Cash, Hoes

Miami. 1998, in a 10th grade photography class that was popular because it had a dark room and a disinterested teacher counting down the days to retirement, the new kid from California whose family relocated to keep him away from gangs befriended me. Took out his Discman in the middle of class, handed me the headphones and told me: listen. The beat that came through the headphones blew. my. mind. I’d never heard anything like it. Then Jay came in over the crazy beat: “J-A-Y, I-flow-sick” Truer words I hadn’t heard. Then, I heard him rap: “Y’all can’t floss on my level, I’ll invite you all to get with us if your ball is glitter. When I go, on the Harlem playas wall, my picture, if you get close enough you can read the scripture, it reads: money, cash, hoes, how real is that? at the end of the first verse, and “sh*t, I led a life you can write a book on. Sex, murder and mayhem, romance for the street. Man, and I tell ya, it’ll be a best seller.” 15 year old me thought: I want that. (minus the murder). I went straight to Best Buy that day after school to spend my hard earned Johnny Rockets money on Vol. 2.

31. I Just Wanna Love U (Give It To Me)

Look, you haven’t lived if you never heard this monster of a song drop in the club just at the right time. What time is that, you ask? Exactly at 1:30 am. The club is in full swing. Everyone who is anyone is already in. You’ve had a few drinks and are just the right amount of confident to dance. You don’t even realize it, but before you know it, you find yourself on top of a table just at the right time when Jay-Z raps, “both in the club, high signing off key: AND I WISH I NEVER MET HER AT ALL” and you actually live out what you are rapping along to at the top of your lungs. It does get better, and you do order another round. You rap every line of every verse, and in that moment you’re not you. You’re Jay and you’re shooting your own version of the music video. It’s a vibe. A vibe that only Jay-Z can deliver.

30. Big Pimpin’

Introspective Jay-Z has dominated the list thus far. But Commercial Jay-Z is just as important. Commercial Jay-Z is important because he paves the way for Introspective Jay-Z. So, this song from the otherwise forgettable Vol. 3…Life and Times of S. Carter, is important for two reasons: it broadened Jay-Z’s audience and platform, and the collaboration with UGK gave credibility to Southern Rap at a time when New York rappers didn’t stray too far from New York. This song also marks Jay-Z’s personal arc in his relationship with/to women, making bold declarations that he’ll be forever pimpin’, which we know turned out to not be the case.

29. Izzo (H.O.V.A)

Jay’s first entry to the Billboard’s Top 10 was this first single from The Blueprint, widely regarded as his other best album. The first being his debut effort, Reasonable Doubt. Izzo is memorable for also providing a historic moment in the history of Hip Hop, when Jay-Z brought out Michael Jackson on stage while performing at the famous Hot 97 Summer Jam. Why did he bring out MJ? Astute ears will recognize a Jackson 5 sample if they listen closely.

28. Ain’t No Playa

An early commercial success, this song introduced Foxy Brown to the masses. It also features Jaz-O, and broke through to the mainstream as part of the soundtrack to Eddie Murphy’s movie The Nutty Professor. This song was also the first of many successful collaborations with Foxy Brown and established a pattern of Jay-Z sharing the mic with female artists at a time when that was rare. Other notable female artists Jay-Z went on to collaborate with include Amil, Mariah Carey, Mya, Rihanna, and his now wife Beyonce.

27. 03' Bonnie & Clyde

Speaking of Queen Bey, this is her first appearance as a co-headliner (she sang the hook in Pray). This song marked the coming out, revealing, or confirming of what was the rumor of the time, that Jay-Z and Beyonce were an item. Beyonce, of squeaky clean image from Destiny’s Child, and former drug dealer rapper twelve years her senior becoming an item was shocking at the time, and the subject of many magazines’ focus. This song affected the culture because it changed the way Jay-Z and Beyonce were seen as artists and as individuals. Beyonce showed she had edge, and Jay-Z showed he had heart. And thus, music royalty was born.

26. Best Of Me, Pt. II

This song doesn’t feature great lyrical dexterity or depth. It does, however, feature ICONIC lines and moments. His “I’m focused, man” at the beginning of the song became a part of hip hop lexicon. The music video had Jay and Mya in matching Jordan carolina blue jerseys, Mya’s a dress. The song showed that Jay-Z could be playful, flirtatious even. Again, not a common look for rappers in the late 90s and early 2000s. And not really well done when attempted by others (see Busta Rhymes and Janet Jackson’s What’s It Gonna Be?!).

Stay tuned. Part II coming soon!