The Guide to Getting into JAY-Z

At times in recent years, it has even felt like Jay is completely removed from his own musical legacy. However, his addition this year as the first rapper in the Songwriter's Hall Of Fame was a stark reminder that for two decades his work has shape-shifted rap music as we know it. His book Decoded proved that as well; his lyrics are so deeply intricate that they required an entire book of deciphering. Musically as of late, Jay has been like a truffle on the track—once added to, say, french fries or mac and cheese (read: a Rick Ross song or DJ Khaled song), the flavor gets elevated, as does the market value.

On June 30, that perception evolved once again. Jay dropped his 13th studio album 4:44, which many have touted as his most intimate work to date. To a large extent, the album is a farewell to Jay-Z and a hello to Shawn Carter, where Mr. Carter is taking rap to new, more adult places. It's completely diminished any assumptions that hip-hop is a young man's game, as we've been told so many times in the past. If anyone on the planet was going to change the hip-hop age gap, it would be JAY-Z. What a time to be a JAY-Z fan, both longtime and newcomer.

This arc probably means very little to the casual JAY-Z listener, yet it's everything to the JAY-Z zealot. That divide is why compiling a list of Jay's greatest work is almost futile. We can try, though. But before we proceed, I'm gonna need those superfans (minus myself) to kindly exit this article. What you would be reading would theoretically offend you. There will be glaring omissions from your favorite JAY-Z playlist—and before you protest, there's no such thing as a Jay fan without strong opinions about the rapper's catalog. There will be a bevy of hits that you've written off as Jay's most flaccid work. You'll present deep cuts from warped cassettes as evidence of your expertise. That's fine; go listen to that stuff on your new Walkman. This talk right here is for the newbies.

Hiya, newbie! Glad I've got you alone. Those zealots are like the intimidating people that surround you in yoga class where you can barely Downward Dog but they're chillin' in a Scorpion Pose. It's okay, it's just you and me now. You might have caught yourself referring to Shawn Corey Carter (that's JAY-Z's government name) as "Beyoncé's husband." Yes, that's disrespectful, but it's fine for this moment. Maybe you remember he sampled the Annie musical, maybe you love when "Empire State of Mind" plays at Yankee Stadium. Maybe your fandom stops there, because you've been waiting for someone to demystify his catalog for you.

Well, here we are.

Understand this: JAY-Z is a renaissance man. His references live somewhere in between the Louvre and Marcy Projects. He's lived many lives jam packed into this one. It's time to get to know all of his sides. Welcome, ladies and gentlemen, to the eighth wonder of the world. The flow of the century. Always timeless. Hov.

Mainstream JAY-Z is any rabid JAY-Z fan's least favorite JAY-Z, but that doesn't mean they won't bump the shit out of these songs in private and run around in circles in excitement when they come on at the club. Jay may be one of the greatest lyricists of all time, but he also knows how to make a hit. In 2003, on The Black Album song "Moment of Clarity," Jay spits some bars on his reasoning for adopting a mainstream approach. "If skills sold, truth be told, I'd probably be lyrically Talib Kweli," he muses, adding, "Truthfully I wanna rhyme like Common Sense / But I did five mill'—I ain't been rhyming like Common since."

After his second studio album, 1997's In My Lifetime, Vol. 1, the cerebral deep cuts were increasingly matched by blockbuster hits. The following year, with 1998's Vol. 2…Hard Knock Life, Jay achieved that referenced five million and saw the utility in those poppier bangers. And yeah, they're all lyrically tight, but it's the bars that have dropped into pop culture as words to live by that prove that Jay can not only cater to the mainstream, but infiltrate the vernacular while he's at it. Take "I don't pop Molly, rock Tom Ford" (off Magna Carta Holy Grail's "Tom Ford") or the entire "H to the Izzo" spelling craze. Hell, he had the Obamas brushing dirt off their shoulders.

None of this is to suggest he abandoned any semblance of depth or meaning in his music; hell, his biggest hit ever, "Empire State of Mind," gives the actual address of his old stash house. There are levels to Jay's mainstream acumen. These are probably the songs that everyday people turn to when they think of Jay-Z. Are these your favorite Jay-Z songs? It's okay to admit it; this is a judgment-free zone, and the truth is that there's a reason these songs got so big.

Playlist: "Empire State of Mind" feat. Alicia Keys / "Holy Grail" feat. Justin Timberlake / "Change Clothes" feat. Pharrell / "Can I Get A…" feat. Amil and Ja Rule / "Hard Knock Life (Ghetto Anthem)" / "Money, Cash, Hoes" feat. DMX / "Big Pimpin'" feat. UGK / "Niggas In Paris" (with Kanye West) / "Tom Ford" / "Excuse Me Miss" feat. Pharrell / "Dirt Off Your Shoulder" / "Run This Town" feat. Kanye West and Rihanna / "Izzo (H.O.V.A.)" / "I Just Wanna Love U" feat. Pharrell
Apple Music | TIDAL

This version of JAY-Z is the biggest reason why I told the zealots to exit the building. The argument over what theoretically constitutes "classic" JAY-Z lives on to this day, and it's no less heated than it was in the early aughts. "Classic JAY-Z" works on a sliding scale, but it's safe to say that quintessential Jay-Z embodies the following criteria: strong bars with production that toes the line between radio-friendly and aggressively underground. The lyrics typically highlight Jay's superiority as an MC, and in many cases they reference his drug dealer past, often with him bragging about ducking the Feds.

He puts it best on "Justify My Thug," where he says: "And I ain't never been to jail / I ain't never pay a n***a / to do no dirt for me I was scared to do myself / I will never tell, even if it means sittin' in a cell / I ain't never ran, never will." Jay has made a career out of proving he was smarter than the law simply by understanding it (listen to the cop scenario on "99 Problems" to truly grasp that), yet emphasizing that he's still no snitch. There's a sound. There's a delivery. There's a vibe.

If you could bottle up "Classic JAY-Z" and sell it in stores, then most of rap's problems surrounding authenticity, skill, and marketability would be solved. Half the reason these even are qualities rap fans debate is because Jay balances all of them so effortlessly. And he knows it.

With classic Jay-Z cuts, there's an underlying shit-talking air to Jay's flow, which is remarkable, especially knowing that he can back up everything he says. Many times there are thinly veiled disses toward other artists—the latest being the jabs at Kanye West on 4:44. No, not the line directly referencing Ye on "Kill Jay-Z." It's the slick one on "Bam," where Jay says: "Niggas is skippin' leg day just to run they mouth / I be skippin' leg day, I still run the world." That's a response to an old Kanye line on "30 Hours," where he says "I hit the gym / all chest, no legs."

When Jay wants to get into Jay form, you can't watch for the hook because it comes out of nowhere. Other times it is overt, like on "Takeover," the diss track from his legendary beef with Nas, where among many other lines he says "Ask Nas, he don't want it with Hov. No!"

Playlist: "Can't Knock the Hustle" feat. Mary J. Blige / "Show Me What You Got" / "D.O.A. (Death Of Auto-Tune)" / "99 Problems" / "Brooklyn's Finest" feat. Notorious B.I.G. / "Feelin It" / "Jigga My N***a" / "Picasso Baby" / "Roc Boys (And The Winner Is)" / "Encore" / "Takeover" / "Public Service Announcement" / "U Don't Know" / "Kill Jay-Z"
Apple Music | TIDAL

When Jay first entered the scene during his pre- Reasonable Doubt era, he rhymed super fast and rhythmically like his mentor Jaz-O. He was known as "Jazzy," which evolved into Jay-Z. As he started accepting his place in hip-hop following his debut album, he began referring to himself as "Young Hova," a nod to his genesis of becoming the god of rap. That later became Jayhova (like Jehovah or full-on god) Hov, Hovi, Hovito (remember his foray into bilingual waters with "Hola Hovito"?). Then of course there was Jigga, which might have been his flashiest era. With every new day of Jay, there's a new name. When TIDAL took off, he went by JAY Z. He's returned to Jay-Z on 4:44 but stylized as JAY-Z, though many will argue he's now the grown-ass Shawn Carter.

But Umlaut Jay is special. Right before Reasonable Doubt hit, Jay spelled his name Jaÿ-Z. It popped up again around a year or two ago. But the timeline is not as important as the qualities Umlaut Jay represents—that is, Jay as his most lyrically complex, the monster of the double entendre (like he says on "Do U Wanna Ride"). Jaÿ-Z throws caution to the wind, and it's just bars after bars after bars.

These are the lyrics that Illuminati theorists point to, the moments when Jaÿ is the most in his head. Sometimes they exist within the same track; sometimes they don't. They're the lines that make you think twice. Like on "Can I Live," where he says "It gets tedious / so I keep one eye open like CBS." The CBS logo is one eye, get it? And try sounding out the letters CBS. Or on "Brooklyn Go Hard," he spits: "I father, I Brooklyn Dodger them / I jack, I rob, I sin / Aw man, I'm Jackie Robinson / Except when I run base, I dodge the pen." Jackie Robinson played for the Brooklyn Dodgers, so Jaÿ breaks his name down to detail his old activities (jackin', robbin', sinnin') and once again moving into classic form, where when he runs base (sells drugs) he dodges the pen (prison). It leaves you with nothing to say but "oh shit."

If you need some straight bars, check "What More Can I Say" which is equal parts cerebral and braggadocio: "But the real shit you get when you bust down my lines / Add that to the fact I went plat' a bunch of times / Times that by my influence on pop culture / I'm supposed to be number one on everybody list / We'll see what happens when I no longer exist."

If you're looking for that graduated level of lyrical superiority that all those Jaÿ-Z experts point to, then this might be your new favorite playlist. A disclaimer: whittling this down to merely 15 songs feels insulting, but we could be here all day when it comes Umlaut Jaÿ.

Playlist: "Dead Presidents II" / "Where I'm From" / "D'Evils" / "Threat" / "Lucifer" / "In My Lifetime (Remix)" / "Coming Of Age" (original and Da Sequel) / "Regrets" / "Streets Is Watching" / "Can I Live" / "Rap Game/Crack Game" / "Renegade" feat. Eminem / "Young, Gifted, and Black" / "Brooklyn Go Hard" / "What More Can I Say" / "Bam"
Apple Music | TIDAL

To say that Jay is a romantic at heart would kind of be a lie. It would be more accurate to say that he picks opportune moments to emote. But that doesn't mean that, as some people have claimed in their analyses of 4:44, he wasn't sentimental until now.

There's no mistaking the significant shift that occurred in Jay's music once Beyoncé entered his life and the even more pronounced change following the birth of his daughter Blue Ivy. But Jay always had in his heart emotions that he had carried since childhood. From not having a strong relationship with his father, to his tumultuous relationship with his brother, to losing friends due to violence or even money, to simply trying to figure his shit out in the midst of fame and fortune, Jay has covered many different struggles in his music. Breaking down these kinds of topics has made Drake a millionaire; but his interest in capitalizing on the intimate "ah-ha" moments when you take the madness down a notch might be traced to JAY-Z, whose music details everything from sex to death.

Certainly, there's been an evolution in Jay's introspective tone. On "Song Cry," he delves deeply into his own head about the missed opportunities to saying things he never got to say, while attempting to keep his ego in tact. Hence the hook: "I can't see 'em comin' down my eyes / So I got to make the song cry." On "Lost One," he extends that discussion, but it gets heavier once he talks about the guilt over buying his nephew Colleek a car that he was later killed in. By "Beach Chair" he questioned if he would be given a daughter as his penance for all of the women he'd wronged (Ta-da! Blue arrived a few years later).

There are other sides to this sentimental Jay beyond ones designed for a leather couch in a therapist's office. There are the cheeky love songs like "Girls, Girls, Girls" where he's lyrically running through women (because #romance) or, of course, anything he creates with Beyoncé—nobody would mistake "03' Bonnie and Clyde" for a sappy ballad, but that doesn't mean it's not a hell of a love song.

When he reached Magna Carta, Holy Grail as "JAY Z" took shape, other things fell out of order. He began to adopt a "fuck it" mentality, which felt like more of a cry for help. "Jay Z Blue" off that album tells it all:

A few years later, Beyoncé would drop Lemonade, apparently highlighting the struggles of their marriage, and JAY-Z would confirm the rumors on 4:44. The fact is, though, that now Jay-Z has thrown all of his cards on the table. He's crafted a project where he's admitted to all of his demons. He's the father of now three children, one of which is the son he's always wanted. Imagine the lyrics to come? Hopefully they'll include Blue, because we know now from her 4:44 freestyle that she's got bars.

Playlist: "Heart Of the City (Ain't No Love)" / "Beach Chair" / "Song Cry" / "03' Bonnie & Clyde" feat. Beyoncé / "Lost One" / "Glory" / "Dear Summer" / "Moment Of Clarity" / "New Day" (with Kanye West) / "December 4th" / "Girls, Girls, Girls" / "Spiritual" / "The Joy" (with Kanye West) / "4:44" / "Adnis"
Apple Music | TIDAL

Get JAY-Z on your record, they said. It will be good for sales, they said. He won't outshine you, they said…

JAY-Z on the track is a golden ticket; the bar is automatically raised. Not a single person in the world would voluntarily invite JAY-Z on a song and then fuck up their chances to sound right. It just won't happen. And Jay looks at these collaborative moments like yoga stretches. Sometimes he'll give a little Warrior pose, other times he'll be doing a Headstand. It all depends on the day and the artist. And don't let Umlaut Jaÿ come into the room because the game will be forever shut down.

Over time, the significance of a JAY-Z feature has changed. He's been known to check in on some crew love, like on Freeway's "What We Do," with the classic line "Bang like T-Mac / Ski mask air it out / Gotta kill witnesses, 'cause Free beard stickin' out." Other times he's a total chameleon, getting socially charged up on Dead Prez's remix to "Hell Yeah": "Now the police, got me in the middle of the street / Tryin' to beat me blue, black and orange / I'm like hold up, who you smacking on? / I'm only trying to eat what you snacking on."

Nowadays, Jay knows his feature is an event, and he makes it work in his favor, whether he's settling beef—as on his Nas feature "Black Republicans"—or weighing in on it. Take DJ Khaled's "Shining," where many people think he's sonning Drake: "I know you ain't out here talkin' numbers, right / I know you ain't out here talkin' summers, right / I know you ain't walkin' 'round talkin' down / Sayin' boss shit when you a runner, right?"

Then, of course, when he's paired with Beyoncé on her work, there's that gushy feeling we get knowing the song is just a big love fest. Or you could listen to all of Watch The Throne to see how he works paired with Kanye West for an entire project. I say enjoy it all. Let it wash over you. Take it all in.

Playlist: "What We Do" (Freeway feat. Jay-Z & Beanie Sigel) / "Diamonds Remix" (Kanye West feat. Jay-Z) / "Drunk In Love" (Beyoncé feat. Jay-Z) / "Hell Yeah Remix" (Dead Prez feat. Jay-Z) / "Flip Flop Rock" (Outkast feat. Jay-Z & Killer Mike) / "Seen It All" (Jeezy feat. Jay-Z) / "I'll Be" (Foxy Brown feat. Jay-Z) / "Black Republican" (Nas feat. Jay-Z) / "Pound Cake" (Drake feat. Jay-Z) / "I Got The Keys" (DJ Khaled feat. Jay-Z and Future) / "Suit & Tie" (Justin Timberlake feat. Jay-Z) / "The Devil Is A Lie" (Rick Ross feat. Jay-Z) / "Monster" (Kanye West feat. Jay-Z, Rick Ross, Nicki Minaj, and Bon Iver) / "Ha Remix" (Juvenile feat. Jay-Z) / "Shining" (DJ Khaled feat. Jay-Z and Beyoncé)
Apple Music | TIDAL

Kathy Iandoli will now be going by Kathÿ Iandoli. Follow her on Twitter.