It’s impossible (and reductive) to boil hip-hop down to a single style or movement. But if rap has a face man, it would probably be Jay-Z, the genre’s most recognizable, successful and enduring icon. He doesn’t have the glowing artistic cred (or the white-hot divisiveness) that his friend Kanye West enjoys. He doesn’t have the hunger that younger artists such as Kendrick Lamar possess. And he didn’t create (or perfect) a specific sound like Dr. Dre did. But at a time when deserving contender Eminem still garners huge sales but diminishing critical clout, Jay-Z stands alone as rap’s grandest superstar—a living legend who keeps putting out multiplatinum albums that double as major events.

Now 43, Jay-Z has managed to remain a big deal for longer than any other hip-hop artist. His debut, 1996’s Reasonable Doubt, is considered a classic, and he has released a few more classics since then—not to mention put out a string of indelible singles in between. His appeal is so ubiquitous that artists as varied as U2 and Justin Timberlake want to collaborate with him, and he even got name-checked on a Paul Simon record.

His latest, Magna Carta Holy Grail, comes at a significant moment both in his career and in hip-hop’s cultural dominance. Where once rap was considered “dangerous”—a startling, new antiestablishment sound challenging rock and pop on the charts—it has now entered middle age. In fact, today it boasts veteran acts aspiring to the heights of Bob Dylan or Neil Young, artists whose careers stretch decades, inspiring several generations along the way.

It wouldn’t be fair to put Jay-Z in the same league as Dylan or Young—different genres, different eras—but he’s probably the first hip-hop superstar who’s both incredibly popular and in a position to think about his legacy. Rap is still too young to have a Bruce Springsteen or a Rolling Stones—an aging warhorse that reliably packs arenas—but Jay-Z is as close as the music has ever come to one.

But his challenge is still the same: How to grow up without getting old. Which makes me wish that Magna Carta Holy Grail were a little better than it is. Though filled with its share of stellar moments, the album finds Jay-Z struggling to reconcile his youthful braggadocio with his new reality as a married father, former Def Jam label president and owner of a burgeoning sports agency that features Kevin Durant as a client. It’s not the responsibility of Jay-Z, who famously claimed “I’m a grown-up for real” on 2003’s “Dirt off Your Shoulder,” to single-handedly ensure hip-hop’s transition into elder-statesman status. But the course he charts on Magna Carta Holy Grail suggests the difficulties inherent in an artist (and genre) trying to continue to evolve.

Although every form of music has its compelling personalities, hip-hop is unique in that its stars’ backstories become an integral component in their appeal. Fans don’t just listen to the songs for the beats; they also to tune in for the latest chapter in their heroes’ underdog adventures. Among rappers, Jay-Z’s backstory isn’t particularly novel—he spent time as a drug dealer and was raised by a single mother after his drug-addled father left them. What makes it distinct is that he’s now been around long enough that he’s triumphed over his early obstacles. While Eminem’s career has been filled with psychodrama—his most recent album, Recovery, is about bouncing back from drug addiction—and Kanye continues to see the world as a hostile place trying to deny him his props, Jay-Z is married to Beyoncé and said to be worth about $475 million. Not surprisingly then, Magna Carta is an overdog tale, which could potentially be as complacent as dad rock—a genre populated by 30- and 40-something rock artists including Wilco and the National singing about suburban middle-class problems such as aging and the perils of committed relationships.

But the longer Magna Carta simmers, the clearer it becomes that Jay-Z’s world takeover is tempered by serious misgivings—the same “What now?” anxieties that, in their own way, fellow veterans Kanye and Eminem have grappled with in their music. But unlike them, Jay-Z hasn’t created obstacles for himself to overcome—his struggle is entirely internal. “I cut myself today to see if I still bleed,” he sings on the moody, skeletal “Nickels and Dimes.” “Success is so sublime / Gotta do that time to time so I don’t lose my mind.”

That might seem like the typical whine of a self-absorbed rock star pondering his own celebrity, but for Jay-Z it’s a far more complicated affair. Despite his success and power, he never forgets that he’s black—and he never lets his audience forget either. Near the end of “Picasso Baby,” a track that details his material aspirations, including owning artwork by Mark Rothko, Jay-Z proactively chastises listeners for scolding his avarice. “Don’t forget, America, this how you made me,” he taunts, the latest in his string of career criticisms about an American dream that rewards initiative but is stacked against minorities who sometimes have to turn to illegal means to get ahead. Of course, the criminal lifestyle remains a staple in hip-hop lyrics—the subject (and its consequences) pervades Lamar’s superb 2012 release, good kid, m.A.A.d city—but Magna Carta measures what happens when someone comes out the other end, the hustling instinct awkwardly transplanted from the streets to the boardroom.

Jay-Z also sounds like he’s grappling with domesticity. On “Jay-Z Blue,” he expresses his parental anxiety in part by sampling some dialogue from Mommie Dearest. (“No wire hangers ever!”)But he turns the campy family melodrama into something far more unnerving, singing to his daughter Blue Ivy about his fears of duplicating the mistakes he saw in his own broken home. “Father never taught me how to be a father, treat a mother,” he confesses, “I don’t wanna have to just repeat another, leave another.”

It’s a more profound rhyme than you might think—and a little more anguished than the typical dad-rock lament. Like rock before it, rap began as an expression of youthful freedom and rebellion, but eventually it must come to accept the realities of adult life in its lyrics. However, as Magna Carta proves, rap’s embrace of marriage and family is far more involved than rock’s, simply because of the class disparity between whites and blacks in America. Plenty of white rock stars came from lower-class, single-parent families—which brings with it its own cultural bigotry—but they’ve never faced the added hardship of racism that further contributes to diminished economic opportunity that can eviscerate black families. “Jay-Z Blue” might be construed as just another song from a famous dad to his daughter, but the racial dimensions within the track heighten the drama, making Jay’s concerns more poignant. “I seen my mom and pop drive each other motherfuckin’ crazy,” he raps, warning, “I got that nigga blood in me / I got his ego and his temper / All is missing is the drugs in me.” If hip-hop has long featured artists toasting their beloved mothers and decrying their absentee fathers, “Jay-Z Blue” turns the page, a new generation trying to correct the errors of the previous one.

Like a lot of rich stars—white or black, rock or rap—Jay-Z spends way too much time on Magna Carta singing about his fame. “Holy Grail,” which includes a cameo from album co-producer Justin Timberlake, kicks off the record and is essentially a tortured love-gone-wrong song sung directly to his fans. (“One day you screaming you love me loud,” Timberlake croons. “The next day you’re so cold.”) And on “Picasso Baby,” Jay-Z recognizes that some supporters are over him—not that he cares: “Even my old fans like, ‘Old man, just stop’ / I could if I would, but I can’t / I’m hot.” That line recalls one that Jay-Z used back in 2001 when he bragged on his Kanye-produced smash “Izzo (H.O.V.A.),” “Can’t leave rap alone / The game needs me.” Despite his arrogance, he was correct then, and he’s correct now—but for a different reason.

Twelve years ago, Jay-Z was setting in motion his bid to be considered one of hip-hop’s greatest artists, taking the torch from slain idols like Biggie and Tupac and carrying it forward, helping to end rap’s gangster era and opening the door to a new decade. Now hip-hop is in the midst of what Kanye famously labeled “luxury rap” on “Otis” from his 2011 collaboration album with Jay-Z, Watch the Throne, which flaunted its creators’ wealth but also their misgivings about the country that fostered their success. Still rolling with the times, Jay-Z has seized on luxury rap as his current principal theme, symptomatic of an era in which hip-hop isn’t just pervasive but also an established, booming industry genre. As it’s expressed on Magna Carta, that theme seems like a fertile one, fraught with social and cultural complexities.

Still, such privileged musings can leave the average listener feeling alienated, whereas the old crime narratives at least had an instantly dramatic component to them. (Not many of us will relate to Jay-Z dissing rival sports agent Scott Boras on “Crown.” It would be akin to soulless corporate entities like Bank of America and Wells Fargo beefing.) But since it would be disingenuous for Jay-Z to pretend he’s still the same street-level hustler he was at the beginning of his career, he has to forge a new path, one that hip-hop’s upper echelon has never faced before.

Magna Carta’s contradiction is the same as the one pulsing in hip-hop itself: How do you reconcile being the champ in an environment where the culture resents you not just because of your success but also because of your skin? These were problems Bob Dylan or Neil Young—or Wilco or Radiohead—never had to face as their style morphed over time. If rock has been about artistic expression and/or the pursuit of hedonistic pleasure, rap has been about striving to find a better life, which creates a life-or-death urgency that most rock artists never experience.

On some level Jay-Z seems to understand this dichotomy: His biting of lyrics from Nirvana’s “Smells Like Teen Spirit” and R.E.M.’s “Losing My Religion” on the new album suggests that he’s transcended hip-hop to become a rock star. In a sense, he’s also trying to transcend the narrow cultural expectations of rap artists. As he sings on “Nickels and Dimes,” “When a nigga go, as the old adage go / You die rich or you die disgraced / So just let me grow.”

In the late 1970s, Young famously sang that aging rockers had to choose between burning out or fading away—and then proceeded to construct an enduring career that argued that those two options weren’t the only possibilities. Since Jay-Z is so enamored with rock stars, hopefully he’ll take a page from the best of them, watching how Dylan and Young and others have been willing to examine the different seasons of their life, expanding rock from a young man’s game into an art form that can speak to every age. Despite its stumbles, Magna Carta Holy Grail is Jay-Z’s attempt to prove that graying rappers can think beyond the get-rich-or-die-trying street mentality. If the album is hit or miss, maybe we should cut Jay some slack: He’s always bragged about being the king, but now he’s trying to be a trailblazer into uncharted territory for hip-hop. Growing up sometimes comes with a few growing pains.

Tim Grierson is Playboy for iPhone’s critic-at-large. You can follow him on Twitter.