Producer(s): DJ Clark Kent
Best line: “The proper etiquette when I drop the subject, verb/ Then the predicate with this rich n—a rhetoric”

Basically, the Robb Report and Lifestyles of the Rich and Famous, Jay uses another Clark Kent beat to “talk jewels and spit diamonds.” He’s kickin’ pimpish luxury while showing off his ability to manipulate the English language like a college professor doing a creative writing exercise. Jigga is literally dropping jewelry on this with the proper etiquette as he drops the subject, verb and then the predicate. 

Producer(s): Ski Beatz
Best line: “At your wake as I peek in, look in your casket/ Feelin’ sarcastic, ‘Look at him, still sleepin’.’” 

He really said, “To, too, two,” 22 times. You can sit there and count ‘em up, and once you’re done with that, you can check out the update in “44 Four’s.” And he also gave us the comical line, “At your wake as I peek in, look in your casket/ Feelin’ sarcastic, ‘Look at him, still sleepin’.’” He just makes it sound easy. Shout out Maria Davis and Mad Wednesday for helping make this a classic interlude. She’s still out here doing her thing. 

Producer(s): DJ Clark Kent
Best line: “Hahaha, I like your style (Nah, I like your style)/ Let’s drive around awhile (Cool, n—a)/ Here’s a thou’/ (A G? I ride with you for free)”

Another smoothed out beat from the late, great DJ Clark Kent, this track is more influential than some might lead you to believe. Not only was it Bleek’s introduction, Lil Wayne & Baby did their own version with “Lil One” off Weezy’s sophomore album Light’s Out — or maybe the sequel on Vol. 2 released in ‘98 was the inspo — either way, Jigga and Making Easy Money Pimpin’ Hoes In Style show off the chemistry they’ve had over the course of their Roc-A-Fella years.

Producer(s): DJ Premier
Best line: “You draw? Better be Picasso—you know, the best/ ‘Cause if this is not so? Ah, God bless” 

I don’t know when the narrative started that Jay wasn’t a storyteller. I guess it reached a fever pitch around the time he was going back and forth with Nas, because that’s always been the Queens MC’s calling card. It just goes to show you that most people don’t listen to music; they just skim through it. Now please, give me the room key.

Producer(s): Jaz-O
Best line: “Promise to stay monogamous, I try/ But, love, you know these hoes be makin’ me weak/ Y’all know how it goes, B”
Best Foxy line: “I got you frontin’ in Armani sweaters/ Before this rap s—t, when you was in leathers and bulls—t Berettas”

“Ain’t No” was most people’s introduction to Jay-Z in ‘96, and with the help of being attached to The Nutty Professor soundtrack (back when movie OSTs were taken seriously), this song really got some traction. It was the first time I had heard of him, and it led me to seeking out some more of his stuff — and it just so happened that my uncle already had Reasonable Doubt in his collection. And while I still enjoy this song, it taught me that the single wasn’t always the best track on an album. 

Producer(s): DJ Premier
Best line: “Can’t do for dolo/ Had to turn away when Tony killed Manolo”

Jay’s verse on here will forever be my favorite. I’ve had it memorized for 20+ years now. “I am two-point-two pound, you barely 125 grams/ Wouldn’t expect you to understand this, money,” and I didn’t at the time because I was still wet behind the ears. He, Sauce and his mentor Jaz all go off over Preemo production, making this one of the best posse cuts of the era. We don’t get tracks like this anymore, because everyone wants to do things over the Internet instead of hitting a studio and going bar-for-bar like the old days, the bad days, the all-or-nothin’ days. (This song also included a sample of another rapper Jay used to beef with.)

Producer(s): Ski Beatz
Best line: The price of leather’s got me/ Deeper than ever and just think, winter’s here/ I’m tryin’ to feel made, n—a”

Most of Jay’s best songs are his B-sides like this one. I wish he would work with Ski again, because this production is luxurious and Hov almost always loses his mind over his beats. This song is like a glass of chilled Cristal paired with a chicken spot sandwich topped with the most expensive caviar. Take the second verse for example; he’s namedropping Tito Caicedo, the jeweler responsible for popularizing the Jesus piece with Biggie, and talking about how he might clean up in Vegas if Tyson loses. Mind you, this is his first album — and the way he’s rapping with so much detail, it makes it seem like the guy knows what he’s talking about.

Producer(s): Knobody, Sean Cane & Dahoud
Best line: “At my arraignment/ Screaming/ ‘All us Blacks got is sports and entertainment/ Until we even”

This is an underrated entry in his catalog. There so many great things about this record, like that Pain In Da Ass Scarface intro that we said word-for-word in hotbox sessions on the block, Mary’s classic chorus, and the s–t Jay is tallking. I was just a kid when I first listened to this, and I remember my older uncle and his friends saying the jewels he was dropping was gospel. I guess you had to live or be exposed to a different type of lifestyle to get what he was saying on the first go-round. That’s probably why the masses didn’t catch on until Vol. 2. 

Producer(s): Ski Beatz
Best line: “If every n—a in your clique is rich, your clique is rugged/ Nobody will fall ’cause everyone will be each other’s crutches”

Another Ski banger, this was my favorite track as a kid. I had this on repeat while “Ain’t No N—a” was all over the radio and the music video was all over TV. I was in love with everything about this song: the beat, the Mecca chorus, Jay’s verses. I really thought I was living lavish on a tropical island in a villa drinking bubbly with a baddie. This is the type of song that comes on and immediately transports you somewhere else. I would also be remised if I didn’t acknowledge one of his most quoted bars are the ones highlighted above.

Producer(s): DJ Premier
Best line: ” I never prayed to God, I prayed to Gotti”

Featuring the voice of another rapper that he eventually ended up beefing with on the chorus (Prodigy) that Premier sampled from another rapper who Jay beefed with (LL), the verses aren’t the the only things that have layers on this track. When someone questions why Jigga is considered the GOAT, play them “D’Evils” and if they still don’t get it, stop talking rap with them. How can you hear him say what he says on the second verse and not understand why this guy is one of the best to ever do it?

I mean, he said: “Thinkin’ back when we first learned to use rubbers/ He never learned, so in turn I’m kidnappin’ his baby’s mother/ My hand around her collar, feedin’ her cheese/ She said the taste of dollars was shitty, so I fed her 50s/ About his whereabouts I wasn’t convinced/ I kept feedin’ her money ’til her s—t started to make sense/ Who could ever foresee? We used to stay up all night at slumber parties/ Now I’m tryna rock his b—h to sleep.”

[insert disappointed 50 Cent GIF]

Producer(s): DJ Clark Kent
Best line: “Time to separate the pros from the cons/ The platinum from the bronze/ That butter-soft s—t from that leather on the Fonz”
Best Biggie line: “If Faith have twins, she’d probably have two Pacs/ Get it? 2Pacs?

First and foremost, I wanna say RIP DJ Clark Kent. He was a legend in two games: rap and sneakers. I mention him because he produced this beat, and he introduced Jay and Big. Two of the best going toe-to-toe in the same studio session? We don’t get that anymore. Everybody would rather email each other’s verses rather than pull up to the studio and feed off the energy in the room.

Imagine watching this in person. Clark did. In fact, this session was the first time either of them met because he accidentally played the beat for Biggie, which then caused a chain reaction to them meeting.

Sampling the Ohio Players’ “Ecstasy,” the record begins with yet another classic Pain In Da Ass intro, where he evokes the spirit of Al Pacino in one of the more memorable scenes in Carlito’s Way, and Jigga lets the beat build before he and Big lose their minds in one of the most legendary back-and-forths in rap history. 

Producer(s): Peter Panic
Best line: “I know I push you to your limit/ But it’s this game, love, I’m caught up all in it/ They make it so you can’t prevent it/ Never give it, you gotta take it/ Can’t fake it, I keep it authentic”

Probably one of the most underrated tracks in Jay’s catalog, “Regrets” is glimpse into the moral battles drug dealers wrestle with on a daily basis. 4:44 is most definitely a landmark project, and his best late-career album, but we gotta remember that he bared his soul more than a couple times during the first half of his career on songs like this one. I don’t know what the hell I was doing as a young teenager playing this joint as if I could relate to any of it. I’m telling you, though; I felt this s–t to my core. He takes the listener into the underworld and shows us how high the stakes really are. This will always be a top 10 Jay-Z song for me. 

Producer(s): Ski Beatz
Best line: “Partna, I’m still spendin’ money from ‘88”

One of the more important songs in Jay’s catalog, it became a centerpiece in the Nas beef because the chorus samples his voice. There’s also the fact that this is a sequel to the street single that uses the same beat and has arguably his best verse at the beginning, and its own music video. And still, it’s one his best records and one of the best beats he’s ever rapped on. Lines like, “Word life, I dabbled in crazy weight/ Without rap, I was crazy straight/ Partna, I’m still spendin’ money from ‘88,” are still randomly said by real rap fans everywhere. We also gotta shout out Ski Beatz once again for the atmospheric production as he was able to capture an affluence most mafiaso rappers could only dream about.

Producer(s): Irv Gotti
Best line: “No more Big Willie, my game has grown/ Prefer you call me William”

This is Reasonable Doubt’s thesis. Jay spells it out for everyone in the intro about how rappers that came up like him put their trials and tribulations on display for our entertainment and asks what fans and executives bring to the table. He then catches flight and floats over Irv Gotti’s sample of Isaac Hayes’ “The Look of Love” with that epic horn section. This is elevated street talk that only the initiated were able to understand when it first dropped. There’s no wonder why it took everybody else a couple of albums to catch up to some of the shit he was kickin’ on not only this song, but throughout this album. And “Can I live?” is still a question someone asks when being pestered or questioned with nonsense, effectively cementing itself within the urban pop culture lexicon after this record came out.