Paul Simon, a man who really puts the "roll" in rock 'n' roll, rolled gently into Madison Square Garden last night for the first of three NYC shows this week, concerts which he claims will be his final three shows ever. There was a dominant mood of low-key reflection throughout the 2+ hour "Farewell Tour," punctuated by some outrageously fun songs ("That Was Your Mother," "Diamonds On The Soles Of Her Shoes," "You Can Call Me Al," "Me and Julio Down By The Schoolyard") that demanded you stand up and dance, even if they hewed closer to "accordion-rock" than anything we think of as "classic rock." It didn't quite feel like a final show, but maybe that's because Paul Simon has always come across like someone you'll miss more than he'll miss you.

It certainly sounded like he is looking forward to spending some time alone. "I know I'm gonna continue to write music, that seems to just come," he said early in the show. "But I'd like to just stop and think a little bit, and maybe take a look around the planets—we're only here for a short time—and try and see the whole big picture of this beautiful gem of a world."

Simon certainly has a great feel for his own brilliant catalogue: the 26-song set was a generous, balanced overview of his career, with songs from almost every period showcasing his many musical strengths and elevating the setlist above your average, obligatory "greatest hits" tour. There were five immortal Simon & Garfunkel songs and five from his solo masterpiece, Graceland; four from my personal favorite album, The Rhythm Of The Saints, six songs from his first three early '70s solo albums, and a couple gems from random albums like One-Trick Pony, Hearts and Bones, and his most recent offerings including So Beautiful Or So What and Stranger To Stranger.

Simon, decked out in a glittery silver jacket and looking every bit like the emcee of some sort of some futuristic jazz/disco revival club, was more expressive and theatrical in his singing than I expected. His voice, still remarkable after all these years, has held up so much better than so many of his contemporaries (see: Dylan, Bob). The sound of his voice was sometimes eaten up by the enormity of his 10-15 member band, who flanked him for much of the night, but it sounded crisp, clear and precise on the more intimate songs. In another life, he could have been a great crooner.

And while he's always been a deceptively disciplined singer, he really ups the dramatics live, leaning into the movement of the words (and getting silly with the likes of "Mother & Child Reunion"). It made me think about how many musicians have secretly and not-so-secretly wanted to be actors—it also made me realize that actor Danny Strong was born to play Simon in a movie.

Another reason it didn't quite feel like a finale: the best performances of the night tended to be the more challenging, mature compositions from his post-Graceland period. That could be heard in the intricate guitar playing of "Spirit Voices," in the exquisite lope of "Dazzling Blue," and in the piano flourishes which concluded "The Cool, Cool River." Even better may have been the songs from his most recent album, In The Blue Light, which finds him revisiting and updating neglected gems from his back catalogue. He was accompanied by yMusic, a half-strings/half-brass chamber sextet, for these revised takes, and they were all revelatory: "Can't Run But" and "Questions For The Angels" were given deeper shadings in their new forms, "Bridge Over Troubled Waters" had a jazzy spin that betrayed none of its vocal heft, and "Rene And Georgette Magritte With Their Dog After The War," which had a McCartney-esque melodic arrangement, revealed itself to be one of his greatest compositions.

But there was no denying that weaponized nostalgia was a tool in Simon's arsenal—no show that starts with a '60s thesis statement like "America" could. It's hard to underestimate how much Simon's songs are intrinsically tied to the '60s, and how much they've come to define that culture. The nostalgia reached its peak in the second encore, as "Homeward Bound" was accompanied by a video tour of Simon's past, including ticket stubs, childhood homes, and moody photos of the songwriter in earlier decades (there were a few glimpses of old sparring partner Art Garfunkel, but not too many). When he was focused on the older material, often alone on stage without the backing musicians, it was like catching up with an old friend who always tells the same (great) stories.

The Baby Boomers in the crowd—which means a lot of the crowd—had single tears falling from their eyes as Simon meaningfully sang the Simon & Garfunkel finger-picked classic "The Boxer." The parting line "but the fighter still remains" sounded closer to "but the fire still remains," like a keystone for a generation who watched their idealism slip slidin' away until they had to grapple with farewell tours.

But the pre-teen sitting in front of me was too busy alternating between Instagram browsing, extreme sulking, and watching a baseball game on his phone to pick up on the fact that back in the '60s, the hopes of a generation could be contained in an allegorical song prominently featuring a piccolo trumpet. When the arena became deathly quiet in appreciation of the show-closing "The Sound Of Silence," the child's mom embraced him tightly, in an attempt to show how meaningful the moment was, and also to get him to shut up and stop bugging her to leave.