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

If you haven’t yet read Part I, check it out before diving in on Part II.

Let’s get back to it:

25. I Love The Dough

Brooklyn has the distinct honor of producing two of the greatest rappers ever, the Notorious B.I.G. and Jay-Z. Even though they were contemporaries in the late 90s, due to Biggie’s tragic death at a young age, the world only got two enjoy the two emcees on the same song two times. I Love The Dough is the last time they shared the mic. Off of Biggie’s Life After Death, Jay-Z leads off and manages to hang with Biggie, who at the time was considered light years ahead of all other rappers. The flows in this song are tight, not much new in terms of subject matter, but the cultural significance of the song is unmatched. Hence its place on this list.

24. Dirt Off Your Shoulder

There have been a handful of producers who have contributed to some of Jay-Z’s best work: Swizz Beatz, Pharrell, Kanye, and Timbaland. Dirt Off Your Shoulders is a Timbaland production and finds Jay-Z in his prime. A single off The Black Album, Jay is no longer shy about claiming his place in history, letting listeners know they’re tuned to the MF greatest. At this point, with all he’s accomplished, you can’t say he was lying. And though if you just give this song a cursory listen, you might not be impressed, this song is significant because it got everyone brushing their shoulders off, including then candidate for president Barack Obama.

In case the magnitude of this isn’t clear, a rapper said something in a song, from a genre with the worst reputation among politicians, that the future first black president of the United States of America would publicly do in front of people whose support he sought. and he was cheered! What other rapper has positively influenced the most powerful person on the planet before Jay-Z? I might have ranked this song too low now that I think about it. But, moving on…

23. Dope Man

What I love about this song:
-Serena Altschul (if you don’t know who she is, please correct this tragedy. Probably the most respected journalist from MTV News after Kurt Loder)
-The concept of Jay-Z putting himself on trial in a song as a critique of the image White America held of rappers
-Jay’s mastery in weaving all of his achievements as exhibits of criminal activities as part of the case against him.
What I don’t love about this song:
-The fact that it was never a single
-That there is no music video to it
-How underrated it is
-That it is on a terrible album effort

22. This Can’t Be Life

Part of rap’s fiber is shedding light to the tragedy of life in the ghetto. Most of the time, rappers speak of what they see, what has happened to others, or in generalities about their own experiences. Some of raps most tragic tales are works of fiction, like Tupac’s Brenda’s Got a Baby, or Andre 3000’s verse about Sacha Thumper on Da Art of Storytellin’ Pt. II. They soften the blow to the audience, but every once in a while rappers put real life on the record, and you see the person behind the artist. When Jay-Z raps about an ex-girlfriend’s miscarriage, you hear Shawn Carter’s pain. This song also got an all-time verse from Scarface that captured grief in a way rarely ever put on record.

21. Song Cry

Speaking of grief put on record, Song Cry had a slow burn of an ascent into Jay’s songs pantheon. Included in an album (The Blueprint) already overflowing with classics, Song Cry got little attention as the last single but proved to be one of the best. In it, a contrite Jay mourns the loss of a relationship due to his behavior. He also mentioned in an interview that this song is another marker in the evolution of his relationship with/toward women, moving away from his womanizing ways and into valuing monogamous relationships if at the very least realizing what he’s lost.

20. Can I Get A…

If Big Pimpin’ catapulted Jay into being a household name, Can I Get A… paved the way. Included in the Rush Hour soundtrack even though it was the first single off of Vol. 2, Jay introduced femcee Amil, boosted Ja Rule’s profile, and delivered a smooth verse in which he asks an imaginary love if she would still love him if he didn’t have the success he has. This was also the first Jay verse I learned to rap flawlessly by heart.

19. 99 Problems

How many rappers have recorded at least one album? A lot, probably. How many have recorded more than two? Considerably less. Now, how many rappers have added phrases into our collective lexicon not just once (‘urrybody in the club getting tipsy, anyone?) but several times over multiple decades? Not too many, but Jay makes that list. And this song is a reason why. Next time you’re with friends, turn randomly to one of them and say “I got 99 problems…” without completing the line and see if they don’t finish it. 99% chance they will.

18. Brooklyn Go Hard

If you have no idea why this song is on this list because you’ve never heard of it, much less actually heard it, click on this link now, listen to it, then come back. From the soundtrack to Biggie’s biopic film, Notorious, this song is an ode to the borough that birthed him. The song was released in late 2008, well into Jay’s career, but this song finds him trying his hand at something he’d never done before, rapping in a Jamaican Patois accent (you may have heard Drake employ this whenever you hear him say ‘ting’). The real highlight of this song, and the reason why it’s ranked where it is, comes in the opening of the second verse where Jay delivers what might be the greatest triple entendre in rap:

I father, I Brooklyn-Dodger them
I Jack, I rob, I sin
Aw man — I’m Jackie Robinson
‘Cept when I run base I dodge the pen

For an explanation of these lines’ greatness, please click here.

17. Politics as Usual

Reasonable Doubt is a 5 mic album for a reason. It’s got impeccable production and depth to Jay’s rhymes. Politics as Usual is no different. Even though Jay-Z was going through an artistic identity crisis (from gimmicky fast rapper to slick mobster), his rhymes are tight as he introduces listeners to the life of a drug dealer. In Jay’s eyes, it’s hardly any different from how elected officials relate with their constituents. Just politics as usual.

16. Otis

This song is from Jay and Kanye’s joint effort, Watch the Throne, an album dedicated mostly to opulence. Both Jay and ‘Ye are at the absolute height of their powers and make no qualms about flexing on us. Otis is the perfect marriage of flawless production, unparalleled braggadocio, and well executed music video in order to give weight to the seemingly basic rhymes. Jay opens the song by claiming he invented swag. And in the opening shot of the music video he and Kanye are seen taking a saw and blowtorch to a Maybach sedan, wearing Jordans, jeans, plain white tees, looking every part of what the song says. In a genre where everyone claims to be the most, Jay stood apart byway of execution, and this song embodies that to perfection.

15. H.A.M.

Another addition to the lexicon. H.A.M. is an acronym you can look up if you’re not familiar with it at this point. The first single from Watch the Throne finds Jay rapping reckless. In a high energy track, Jay describes different metaphorical scenarios in which he faced great adversity yet remained victorious. He switches flows midway through his verse and manages to deliver one of the most devastating insults to other rappers when he raps:

Ni***s fantasize about the sh*t that I do daily
Like these rappers rap about all the sh*t that I do really
I’m like, “Really; half a billi,’ n***a, really?” You got baby money
Keep it real with n***as, n***as ain’t got my lady’s money

14. My 1st Song

The blueprint to why Jay doesn’t fall off, quoted by Obama as inspiration on how he stays steady. ‘Nuff said.

13. Empire State of Mind

13 years from when he first released an album, Empire State of Mind was Jay-Z’s first number 1 single. An epic, if not beautiful love song to New York City, Jay really captures the essence of what makes NYC so special. Before Drake became Instagram’s most quotable rapper, Jay was giving us line after line that could serve as our favorite instagram post’s caption:
“I’m the new Sinatra, and since I made it here I can make it anywhere”
“You should know I bleed blue, but I ain’t a Crip though”
“City of sin is a pity on a whim, good girls gone bad, the city is filled with them” (this is the ex-girlfriend special)
“Came here for school, graduated to the high life, ball players, rap stars, addicted to the limelight” (another ex special)
But beyond that, when you listen to this song, if you are from New York you beam with pride and puff out your chest. If you lived for a period of time in New York, you can close your eyes and picture everything Jay raps about and you lean into the since I made it here I can make it anywhere line. And if you’ve never lived in New York, you are inspired to move there one day. What more can you ask for from a song about a city?

12. Hard Knock Life

A perfect marriage of Broadway theater and rap with a memorable beat, this song marked a distinct difference between old and new Jay and truly became an anthem. Elsewhere in this list I’ve mentioned how Jay-Z’s style of flow evolved from gimmicky to more confident, but this song is where Jay found his voice, made a play for the GOAT title and never relinquished it. The switch from rap being his side hustle to his full time job was made on this album, but he reminds listeners that the hustle still can’t be knocked when he raps
“Hustlin’ is still inside of me, and as far as progress, you’d be hard-pressed to find another rapper hot as me.”

11. Takeover

Back at the bottom of this list I talked about Super Ugly, the diss track in which Jay took it too far in rap’s last great beef. The precursor to that is Takeover. A menacing song that forces you to bob your head, furrow your brows, and curl your lip on every listen. Takeover starts slowly with Jay mostly bragging about himself and taking general shots but in the third verse he ramps up the intensity and rhetoric to deliver devastating bars. There is a lot of history behind what brought this song about, but the thing to know is this was Jay’s best shot in the biggest rap battle that didn’t end in death. And though the beef did need to be de-escalated, it saw two of New York’s greatest emcees go blow for blow. (Jay did lose, though. Let’s be clear on that)

10. Diamonds From Sierra Leone (Remix)

The original single was from Kanye’s debut album, and it was a good song on its own. But Jay-Z hopped on the remix and made it a classic. It’s not even his song and it’s his 10th best work. All on the back of two parts from his verse. First, probably one of Jay’s most iconic lines, if not one of rap’s most iconic lines in which he says: “This ain’t no tall order, this is nothing to me. Difficult takes a day, impossible takes a week. I do this in my sleep. I sold kilos of coke, I’m guessing I can sell CDs. I’m not a business man. I’m a business, man.” Then, when referencing all the artists he’s brought into the game, he managed to inadvertently obliterate his own man’s (Memphis Bleek) career with the following rhymes:
“Bleek could be one hit away his whole career. As long as I’m alive he’s a millionaire, and even if I die he’s in my will somewhere. So he could just kick back and chill somewhere. Oh yeah, he don’t even have to write rhymes, the Dynasty like money last three lifetimes.”
No one’s heard from Memphis Bleek since. But we can safely assume he’s chillin’ somewhere.

9. Can I live

Not a single from Reasonable Doubt, but there’s a lot of lore to this song. From how it was produced, to what each line from every verse means. But, needless to say, this song is universally understood to be one of Jay’s best. Not just because the production was excellent, and his flow was smooth, but because he introduced relevant themes that resonate 26 years from the day the song/album were released. What question is more timeless than one that asks if one can live?

8. Brooklyn’s Finest

The first of only two collaborations between Jay-Z and Biggie, this is from Reasonable Doubt. The format of this song is unlike most modern collaborations we hear today in which a rapper will rap a full verse, and the next artist their full verse. In this song, Jay and Big trade rhymes back and forth in a pass the mic format as they lay claim to why no one is as good as them. Released in 1996, this song was recorded at a time when Tupac was taking shots at Biggie, who never fully responded. The closest we got to a response on record was this memorable line from Biggie: “If Faye had twins, She’d probably have two pacs. Get it….Tu, Pacs?” (For an explainer on their beef, see here). Early in their careers, to claim they were Brooklyn’s finest seemed a bit premature but turned out to be prophetic as Biggie achieved GOAT status after his death and having released just two albums and as Jay went on to have rap’s longest and most successful career, not just in music but in business.

7. Dead Presidents II

Fun facts about this song, this is a sequel. The first version of Dead Presidents is what was used for the music video, but that version is NOT the version that made the album. And though the beat is the same, the verses are different, and had Jay not recorded DPII, I probably wouldn’t have ranked it at this position. DPI’s verses were a little cornier, flow had more of that rapid fire gimmicky pace, and less verses. On DPII, Jay brings it from the jump: “To the death of us, me and my confidants, we shine. You feel the ambiance, y’all n****s just rhyme. By the ounce, dough accumulates like snow. We don’t just shine, we illuminate the whole show.” Four decades after he spit those bars, they remain true. This song was also the seed that grew into the battle between Nas and Jay. From Nas’ The World Is Yours remix, Nas says “I’m out of presidents to represent me” which caught Ski Beatz’ ear who produced DP for Jay. At one point Nas was invited to record those lines on Jay’s record but it never happened. Fast forward six years later and on Takeover Jay told Nas two things: “Yeah, I sampled your voice, you was using it wrong. You made it a hot line, I made it a hot song.” Which is one of the best disses in rap, but then he added insult to injury by revealing: “And you ain’t get coin, n***a, you was getting f*cked then, I know who I paid, god, Serchlite Publishing.” OUCH.

6. N****s In Paris

There’s no other way to describe this song other than iconic. In 2011 when it dropped, it took over everything: internet, airwaves, blogs, magazines, conversations. You couldn’t breathe without being aware of this song one way or another. And it was well deserved. I don’t know how to describe music, but this beat was unlike anything out at the time. It was high energy, but controlled and refined. It sounded luxurious. It was played back to back to back when it first came out. Jay and Kanye would play it multiple times in a row to close out their concerts on tour and people lost their minds every. time. It was unreal. Jay’s verse has several memorable lines: “This sh*t crazy, y’all don’t know that don’t sh*t faze me. The Nets could go 0 for 82 and I’d like at you like this sh*t gravy” (At the time, he was part owner of the soon to be Brooklyn Nets). Another one: “Psycho. I’m liable to go Michael, take your pick: Jackson, Tyson, Jordan, game 6.” (not the first time rapper had done this. On Victory Biggie rapped: “I perform like Mike, anyone-Tyson, Jordan, Jackson.”). But Jay’s best rhyme from this song is: “I’m shocked too. I’m supposed to be locked up, too. If you escaped what I’ve escaped, you’d be in Paris getting f*cked up too.” Knowing what I’ve escaped, you know what’s going on the ‘gram when I make it to Paris.

5. Rock Boys (And the Winner is…)

A victory lap when there were still more victories ahead is what I call lapping the competition. This was Jay not letting his foot off the gas. Quick story: I lived in NYC at the time that this song was released, and turned 26. After seeing the music video to this song, I made that the theme to my party. Everyone needed to come dressed to impress. I managed to secure a room in a lounge that turned into a club, and threw the party of my dreams, this song, of course, played throughout the night.

Oh what a feeling, I’m feeling life

But beyond what it meant to me, Roc Boys had lush production. Roc Boys felt like the celebration of all the work Jay had put into his craft. It’s this high in the ranking because of what it represents: domination. And Jay-Z didn’t have to rap with the craziest flow, or the deepest vocabulary to let you know.

4. The Story of O.J.

One thing that Jay-Z has always been is aware of how different it is to be black in this country. Throughout his work, time after time, he’s talked about it. So much so, that he’s produced one of the most robust critiques of the inequalities that blacks routinely face. This song finds Jay as an elder statesman in hip hop. No longer the cultural game changer he once was, instead, he uses his place at the top not to speak down to others any longer but to pull them up. The Story of O.J. is instructional in that way: “Financial freedom my only hope. F*ck living rich and dying broke. I bought some artwork for one million, two years later, that sh*t worth two million. Few years later, that sh*t worth eight million. Can’t wait to give this sh*t to my children. Y’all think it’s bougie, I’m like, it’s fine. But I’m trying to give you a million dollars worth of game for $9.99” Valuable advice worth following.

3. 4:44

The final evolution of Jay in relationship to women, this album and song followed Beyonce’s Lemonade, in which she excoriated him for betraying their wedding vows, and was his apologetic response to her. If Beyonce painted a picture of what he’d done without saying it, he admitted to it all mentioning specifics. For a couple that had grown to be notoriously cautious and projected the most guarded image, Jay-Z pulled back the curtain to show just how similar to us all their struggles are. The admission that he saw the innocence leave his wife’s eyes struck me, because who Beyonce is today is worlds apart from who she was when she started out with Destiny’s Child. Not to take away anything from her agency in the choices she made to be who she wants to be, but the line feels aptly descriptive of how Beyonce relates to her fans now. Sometimes that’s necessary, but we’re not always aware of the moments when we lose our innocence. I can’t imagine what it must do to someone to be able to see that and feel partly responsible. Nevertheless, Jay shows real courage to own up to it publicly. To do this and fight for his marriage in a culture where celebrity divorces (for lesser offenses) are so common, and even more so among minority marriages, was monumentally countercultural because it showed black men and women that if Jay and Bey could go through something that painful and work through it, that they could, too. The way he speaks into fatherhood is also not something that would be familiar to many of the black men who would listen to his music, or even him, whose own father wasn’t around. So, to express remorse and guilt at the thought of having to explain to his children what he did is not just rare but unheard of in rap and hip hop culture.

2. Part II (On The Run)

But if one wonders how Jay and Beyonce were able to fight through his infidelities, Part II has hints of what they mean to each other, and how fiercely Jay is willing to defend his relationship with her. From his Magna Carta album, this song was recorded and released before 4:44 and everything that brought that album about had unfolded. Yet, Jay speaks to Beyonce’s loss of innocence in a different way here. In the first verse he says: “I been wildin’ since a juvi, she was a good girl til she knew me. Now she’s in the drop bustin’ uey’s.” But the closing of the second verse, he admits what she’s done for him that makes their relationship so meaningful. And, truth be told, what he says is also something that makes my own marriage so special: “She fell in love with the bad guy, the bad guy. What you doing with them rap guys, them rap guys. They ain’t see potential in me girl, but you see it. If it’s me and you against the world, then so be it.” And that type of admission is just not something commonly expressed in rap. Men brag about how great they are, and how desired they are. They don’t admit to feeling less than by others, much less that the potential that their spouse sees in them helps them believe that they can change and grow to be better. This is the culmination of jay’s evolution from objectifying women as disposable means to an end to valuing a woman’s worth and celebrating them. The irony is that despite expressing this about his wife, he wasn’t living that out completely, hence 4:44. But at the time when this song was released, no one knew that, and it was the true love song rap had never had.

1. Renegade

The songs at the top of this list aptly find Jay in his later years, much like Michael Jordan winning his last title in his late thirties, or LeBron winning his latest trophy in his 17th season. So, it might feel like we’re taking a step back by going back to a song off The Blueprint, which came out in 2001. But, this song is still relevant 19 years later. on Renegade Jay teams up with Eminem (one of the few rappers that has maintained the same level of artistic output and success as Jay-Z) to address their critics. But, let’s just get this out of the way because it needs to be said: Nas spoke truth on Ether, his response diss track to Jay’s Takeover, when he said: “and Eminem murdered you on your own sh*t.” This is a fact. But, it’s a testament to how great this song is that despite Eminem besting him, this is still Jay’s second greatest song. Second greatest? yes, there’s one more. But before we talk about that, more on Renegade. A common critique of Jay-Z was that he just made party music as opposed to rappers like Nas and others. So he starts out by addressing that saying: “Motherf*ckers say that I’m foolish, I only talk about jewels. Do you fools listen to music or do you just skim through it? See, I’m influenced by the ghetto your ruined.” A few bars later: “The renegade, you been afraid, I penetrate pop culture, bring ’em a lot closer to the block where they pop toasters.” Commercial Jay-Z paving the way for Introspective Jay-Z. His flow on this song is also unconventional, and almost matches Eminem’s own dexterous flow, showing he could stylistically keep up with anyone. Nineteen years later, turns out it was other rappers couldn’t keep up with him.

GOAT: Glory

I didn’t include this song as part of the numerical ranking because it’s a special song not included in any album or on any soundtrack. It didn’t get a video made, not an official one anyway, and Jay doesn’t perform it often. So, why is this his greatest song? Because out of all his accomplishments, accolades, and successes, he declares his greatest creation to be the birth of his daughter. And he’s not wrong. It’s not even up for debate. To contextualize why this is his greatest song, a short personal story: I also have a daughter. At the hospital, as we were about to go home, I went out to my car to get the baby seat and on my way back to the room, a random guy saw me with the baby seat and asked me if it was my first. I proudly said yes. Boy or girl, he asked. Girl, I beamed. With regret he said to me, aw, there’s always the next time. Meaning, maybe I’ll get a boy next time. And the harsh truth of how women are seen and valued in the world was exposed to me just 3 days into my daughter’s life. So, for what some people see as the most alpha of alpha males, wildly successful, married to one of the most desirable women who is equally as successful as him, for him to celebrate his daughter through the art form in which he’s dominated so many men, to use that as the vehicle to pay the highest praise to his daughter is revolutionary. Deeply personal and moving, his best artistic expression is about the greatest human creation. Glory, indeed.