“Kill Jay-Z,” raps Jay-Z in the first line of the first song of his newest album, the cryptically titled 4:44 (some have read it as a reference to Obama, the 44th president). “They'll never love you/You'll never be enough, let's just keep it real, Jay Z” continues the man who once said, “no question; Jay-Z got too many answers” on his 1996 debut Reasonable Doubt. Yet here he is, all this time later, sounding like a man with no answers, learning from scratch. In the intervening years he has weathered the murder of his friend and fellow Brooklyn legend Biggie Smalls, sold 55 million albums, amassed a net worth of $810 million, pled guilty to second-degree felony assault over a nightclub stabbing, retired, unretired, married Beyoncé, became a father three times over, and cheated on his wife only for his philandering to become a main subject of her widely adored 2016 album Lemonade.

 

Did these experiences wear him down? Is the new Jay-Z essentially a depressed king moaning about the weight of his crown and the shame of his betrayals? Or is there something else at work? Perhaps those wild years have made him more honest, stripped away the tin armor. Discussing his decision to go to therapy in a recent interview, he spoke of the false courage of street kids in his childhood projects, Bed-Stuy’s Marcy Houses:

 

I was just saying there was a lot of fights in our neighborhood that started with “What you looking at? Why you looking at me? You looking at me?” And then you realize: “Oh, you think I see you. You’re in this space where you’re hurting, and you think I see you, so you don’t want me to look at you. And you don’t want me to see you.”

 

Putting on a tough shell to deflect pain – it’s a truth that Jay-Z is finally wrestling with, though old habits are hard to break.           

 

To understand how the 48-year-old rapper got to this point it’s necessary to back up a few years to when he released his best album at the height of his powers, at a moment that – through no doing of his own – proved to be a turning point in history. Jay-Z released The Blueprint on September 11, 2001 – an unfortunate release date if there ever was one. Had the album been anything less than a masterpiece it would have floundered, but instead it became a symbol of strength for post-9/11 New Yorkers, an affirmation that even the most catastrophic of events couldn’t dampen the resilient spirit of the city.

 

It was a turbulent time for Sean Carter as well – he had pled guilty and received probation for stabbing Lance “Un” Rivera in a New York club over bootlegged copies of his previous album – but his Jay-Z persona was as defiant as ever. “Mr. District Attorney I'm not sure if they told you,” he smirked, “I'm on TV every day, where the fuck could I go to?” He sounded unstoppable.

 

But nestled among the braggadocio and crime tales was the gorgeous Just Blaze-produced “Song Cry,” a song he says is about his second serious girlfriend, a woman named Fannie. In a 2003 interview with Vibe, he admitted that his “level of commitment to her couldn’t compete with what I was willing to give to make this rap thing work.” The song’s lyrics stand out for their blunt honesty and emotion, admitting that women used him for his money. “It was the cheese, helped them bitches get amnesia quick/I used to cut up they buddies, now they sayin' they love me/Used to tell they friends I was ugly and wouldn't touch me.” Yet even in those vulnerable moments, he was reserved: “I can't see it comin' down my eyes/So I got to make the song cry.” The tough guy mogul had feelings too, even if he had a hard time showing them.

 

All of this is to say that a sizeable chunk of Jay-Z’s most recent album can be seen as an extension of that one song. Gone are the fake Scarface of Reasonable Doubt and the doo-rag and jersey-clad hustler of Vol. 3… Life and Times of S. Carter. The new Jay-Z is a philosopher of race and economics, a loving father, and, perhaps most significantly, a remorseful cheater.

 

The title track is an apology to his wife Beyoncé for infidelities that have been tabloid fodder since at least 2014, when video footage came out of her sister Solange kicking him in an elevator while Beyoncé looked on impassively. In a reference to the Isley Brother’s “At Your Best (You Are Love)” he raps, “And I apologize 'cause at your best you are love/And because I fall short of what I say I'm all about/Your eyes leave with the soul that your body once housed.” On first listen it appears the dense rapid-fire patter of his earliest 90s verses has slowed down to something simpler and less impressive. But listen to the way he says “eyes leave” to sound like “Isley,” layering references back on top of themselves.

 

Expressions of anxiety and depression don’t come as naturally to Jay-Z as they do to other rappers. While Biggie’s self-loathing and paranoia bled into every verse of “Suicidal Thoughts” and Future’s heartbreak and bitterness made “Throw Away” into one of the standout rap tracks of recent years, Jay-Z always seemed a little too icy and aloof for such displays of naked vulnerability. He was the Teflon don (“I never prayed to God, I prayed to Gotti”), the Bentley-driving kingpin who seemed most comfortable in a suit puffing on a cigar, shades on and head tilted back. Hearing him remorseful and ashamed after two decades of unbroken confidence can be jarring.

 

“The Story of O.J.” was released along with a black-and-white animated music video that harkens back to the minstrel era and stands as the album’s most explicitly political statement. There’s a note of pessimism to the chorus, a meditation on the inescapability of racism regardless of economic status: “Light nigga, dark nigga, faux nigga, real nigga/Rich nigga, poor nigga, house nigga, field nigga/Still nigga, still nigga.” It’s a darker statement than the Horatio Alger fantasies of his earlier material.

 

So what’s the solution? This is where the song goes off the rails, advocating a “pull yourself up by your bootstraps” approach that wouldn’t feel out of place coming from Bill Cosby or Milton Friedman. “You wanna know what's more important than throwin' away money at a strip club? Credit/You ever wonder why Jewish people own all the property in America? This how they did it.” Let’s put aside aside the fact that most Jews in America aren’t rich, and that most rich people in American aren’t Jewish. What exactly does he expect working class black youth to do? Become loan sharks? Start a bank? Invest what little savings they have, if any, in start-ups? Take out loans to fund their own risky entrepreneurial ventures? Most of the struggling millenials he’s preaching to are on the wrong side of the credit equation anyway, drowning in credit card and student loan debt. He wants to pass down the keys to success, but he ends up coming off like a middle-aged CEO telling the 22-year-old mailroom guy to be more ambitious. How, exactly?

 

This is the problem when rappers who portray themselves as boss figures get political. Jay-Z’s multimillion-dollar rap career is an unbelievably rare occurrence. Thousands of young rappers try to follow in his footsteps every year and fail, while a few dozen find a fame that almost always proves fleeting. He is the exception, a near-miracle – the closest thing rap has to Michael Jackson in terms of sales (it’s no coincidence that he brought out the King of Pop for a guest appearance at Summer Jam in 2001). As a result of his position at the top of the financial pyramid, his advice to those with nothing is tone deaf and patronizing. It manages to come across as both anti-capitalist and hyper-capitalist, philo-Semitic and anti-Semitic, clever and stupid. 

 

The album’s best material is the most personal. “Marcy Me,” a tribute to his old Bed-Stuy stomping grounds, is the bleeding heard of the album. Over a slow, loping beat tailor-made for nostalgia, he conjures pictures of a pre-gentrified Brooklyn, before the yoga studios and coffee shops, when gangsters like Haitian Jack roamed the streets and shooters took aim from the tops of buildings: “Old Brooklyn, not this new shit, shit feel like a spoof/Fat laces in your shoe, I'm talkin' bustin' off the roof.” It’s the song most firmly rooted in the Brooklyn of his childhood (“Shout out to Nostrand Ave., Flushing Ave., Myrtle”), a near-mythical setting that has been eaten away slowly by the homogeneity of yuppies and condos. The accompanying video by the Safdie Brothers—directors of Good Time, 2017’s best film—bridges this divide well. A young boy running errands tries to escape the spotlight of a police helicopter over the projects, a holdover from that earlier, rougher era.

 

Another high point is “Bam,” a soaring, irresistible collaboration with Damian Marley based around a sample from Sister Nancy’s dancehall classic “Bam Bam.” It’s the one song on 4:44 that carries the pure joy of “Hard Knock Life” or “H to the Izzo” (though it most closely resembles Kanye West-produced “Lucifer,” which similarly makes use of an infectious old reggae sample).

 

“I'll Bobby Shmurda anybody you heard of,” he announces with the swagger of a heavyweight champion, and for a second he almost sounds like the old Jay-Z.