Over the last three-plus decades, Jay-Z extricated himself from a life of drug dealing to become one of the defining rappers of all time. He has owned part of an N.B.A. franchise, invested in fashion, technology and liquor brands, and become the liaison between the N.F.L. and the pop music world. He’s partnered with corporations including Amazon, Target and Sprint. To say nothing of marrying Beyoncé and fathering three children.

So maybe the test of strategic acumen he faced at around 20 minutes after midnight early Monday morning was, comparatively, light work. At that point, the start of his Yankee Stadium show had been delayed around three hours, owing to crowd surges at the entrances. Tens of thousands of people inside the stadium were politely agitated, trapped in a kind of purgatory, wondering if there would be a show at all.

When Jay-Z finally took the stage, he leaned in like a crisis P.R. professional. With equanimity and certainty, he assured the crowd that their patience would be rewarded. And then, while the city that never sleeps slipped into quiet mode, Jay-Z went to work, turning the greatly delayed performance into a transcendent and dizzying affair — a deeply memorable entry in a long catalog of memorable events.

It was the third of three sold-out nights at Yankee Stadium, each show centered around a different segment of Jay-Z’s career. Taken in sum, they had the air of ecstatic boosterism. But lurking beneath were thoughtful reckonings, mild anxieties, a stubborn commitment to art that survived decades of commercialism and commercialism that survived decades of art.

That was encapsulated in the difference between the first two shows. Opening night, focusing on his intimate and gloomy 1996 debut album “Reasonable Doubt,” was about narrative, an establishment of bona fides and a testament of shared understanding with his longest-standing fans. The second show, focused on his 2001 album “The Blueprint,” was an uncomplicated celebration of both Jay-Z’s peak era of relentless hit-making and also the heights to which the genre was able ascend upon his shoulders.

The third and most roisterous night, billed as “Extra Innings,” proved to be an omnibus take on the full of his career, but its most remarkable moments were its most plain. Jay-Z remains, after all these years, probably the most technically adept rapper to have ever achieved mainstream superstardom. Somewhere past 1 a.m., he launched into a set of outlandishly intricate verses — the freakishly pointillist “Jigga What, Jigga Who,” the offhandedly flashy “Clique,” the somber close-listen “Dead Presidents II.” One man, rapping with dexterity and flair, commanding a stadium full of fans: By the standards of modern, grand-scale hip-hop concerts, these performances were almost quaint. Apart from the 3,000-square-foot video screen and the occasional fireworks display, they could have just as easily been at Carnegie Hall (where he has performed a full concert before) or Lincoln Center (not yet, but certainly someday).

Plenty of other startling things happened, too. There was an appearance by Rihanna — whom Jay-Z had signed some 20 years ago back when he was president of Def Jam — that felt like a conflagration despite her demurring, “Y’all know I’m rusty, right?” There was the great Atlanta rapper Jeezy, there for the “Go Crazy” remix that Jay-Z apparently hasn’t performed in a decade, and which was his most joyful moment of the night. Usher emerged to sing the hook on “Heart of the City (Ain’t No Love),” one of the few renditions that meaningfully altered the song. After Pharrell performed a mini-set of club classics for the second night in a row, his protégés Clipse played their drug-dealing anthem “Grindin’.” Moments later, Beyoncé took the stage with around 20 dancers for an ethereal and muscular mini-medley of smashes, one of the night’s most jarring transitions that still managed to feel comfortable under Jay-Z’s vast thematic umbrella.

That all this was happening in the dead middle of the night, in a space enclosed at the sides but open to the heavens, gave the whole affair a sense of privacy, as if the stadium were occupying a slightly askew plane of existence. Nobody — onstage or in the crowd — seemed inclined to leave. Literally thousands of grown men were toting JAŸ-Z-30 merch bags like Birkins.

By comparison, the first two concerts were straightforward affairs. “The Blueprint” is one of Jay-Z’s most popular and musically vibrant albums, and his tour through it was like careering from one prizefight anthem to the next, including the cheeky “Izzo (H.O.V.A.)” and the titanic “U Don’t Know.” Toward the end of the set, Eminem joined Jay-Z onstage to perform “Renegade,” their much-debated collaboration, showing off two opposing styles of grand-scale technique.

Tackling “Reasonable Doubt” the prior night, Jay-Z was both less excitable and more reverent. It’s an album of inner ramblings, single-act theater monologues and show-off skill. Apart from a handful of flashy moments — say, Beyoncé singing the Mary J. Blige parts on “Can’t Knock the Hustle” — he mostly focused on dexterity (“D’Evils,” “22 Two’s”) and solemnity (“Regrets”). The most notable guest was Nas, with whom Jay-Z famously quarreled, though now the two men have achieved a grown-folks rapprochement.

Seemingly in a nod to this adult peace, Jay-Z left “Takeover” out of his performance of “The Blueprint” — one of his most diabolical dis songs, its absence suggested if not maturity, then at least pragmatism. The same was true when Jay-Z’s eldest daughter, Blue Ivy, performed “Feelin’ It” on piano. You could sense him anxiously skipping around some of the song’s raunchiest lines.

This was one way Jay-Z navigated some of the more delicate negotiations of his old and new selves. But nevertheless, there were ghosts hovering over these shows, people integral to his lore who were felt deeply by their absence. The Notorious B.I.G. — who was killed in 1997 — made for his best sparring partner on “Brooklyn’s Finest” (though the version here, with some of B.I.G.’s songs spliced into the beat, felt overwrought). Kanye West (now known as Ye), was one of the two sonic architects of “The Blueprint,” and was once Jay-Z’s main protégé. But his loathsome public outbursts have made him persona non grata, in this context and many others, even though he was once Jay-Z’s loudest cheerleader.

Those who did show up underscored Jay-Z as both student and benefactor. For “Bring It On,” from his debut, he was joined by Jaz-O, the Brooklyn rapper who gave him his first break. And he welcomed Slick Rick for “The Ruler’s Back.” These were extremely local gestures for a globally scaled concert, but they reinforced how Jay-Z views himself and his triumphs — as an extension of rap tradition, not a violation of it. He passed on the good will to others, including Jeezy, Clipse and the Atlanta maestro Jermaine Dupri, often excluded from New York-centric conversations about rap greatness, on “Money Ain’t a Thang.”

There was ample setlist overlap across the three shows — versions of “______ in Paris” (joyful) and also “Empire State of Mind” (groan-worthy). And throughout the three nights, there were winks at songs left unperformed, whether the sinister “Do It Again (Put Ya Hands Up)” or the disarmingly casual backdrop for his famed 1995 freestyle alongside Big L on “The Stretch Armstrong and Bobbito Show.”

These served as indicators that no matter how complete these kinds of performances are intended to be, they can only scratch the surface for an artist who’s been active for more than 30 years. The roads not taken here are almost as fruitful as the ones he chose.

Which is especially meaningful when considering that Jay-Z is 56 now, and may never again perform shows of this scale, in this fashion. Perhaps a multinight residency at the Barclays Center, or Sphere in Las Vegas? Or maybe a set of far quieter and more intimate rooms, in which he can express the fullness of his wordplay without the pressure of signaling to the cheap seats? (Though at this weekend’s shows, none of the seats were particularly cheap.) But the one-man Coachella that he orchestrated may not be viable, or attractive, a few years down the line.

That lent an extra dash of urgency and anxiety to Sunday night’s — check that, Monday morning’s — performance. After the hours of holding pattern, Jay-Z presented as being on a crusade against time, against logistics, against the dropping of the curtain. As the show stretched toward 3 a.m., he made it clear that for him — for now, at least — bedtime is a suggestion, not a rule.