All for the Hall 2015: Paul Simon, Brad Paisley Trade Riffs and Jabs

Vince Gill, Emmylou Harris and Carrie Underwood also join the stripped-down New York show, to benefit the Country Music Hall of Fame

Carrie Underwood, Brad Paisley, Emmylou Harris and Vince Gill were part of the 2015 All for the Hall show in New York. Credit: Rick Diamond/Getty Images for Country Music Hall of Fame

Vince Gill began last night's All for the Hall guitar pull by reciting one of the entertainment industry's most persistent clichés: "It's just fun," he told the crowd at the PlayStation Theater in Times Square, "You never know what you're gonna hear." Well, with Paul Simon, Emmylou Harris, Brad Paisley and Carrie Underwood sitting beside him, everybody in the audience had a few guesses, whether it was classics like "The Boxer" or recent hits like Underwood's "Smoke Break." Both of these tunes were in fact played to great applause, but that doesn't mean the host and 20-time Grammy winner was lying: The artists' song choices may not have been entirely unexpected, but the show they put together was joyously unscripted.

The All for the Hall events take place annually in Nashville and bi-annually in New York and Los Angeles, alternating between coasts each year. Proceeds — significant because the show began with a swanky dinner and a raffle in which a private performance by Gill and Harris fetched $95,000 — benefit the Country Music Hall of Fame and Museum.

As is custom, the performers were backed only by an acoustic guitar or two, and the music started as soon as the food was cleared. Harris went first, singing "My Songbird" in honor of its author, her recently deceased friend Jesse Winchester. Next up, Paisley followed her lead, doing a little bit of "Country Boy" in honor of his own recently deceased friend, Little Jimmy Dickens. He then shifted into his own "Southern Comfort Zone." "This is a dream I have," he said of his role in the event. "But I'm usually naked."

Rather than play her own guitar, Underwood was backed by a guy whose all-black formal outfit gave off a strong Secret Service vibe, making at least one person in the room envision a scenario where he jumped into the crowd to save her from a would-be assassin. This didn't happen, but he did add some pep to "Smoke Break." Under the subsequent applause, Simon began to tease the intro to "The Sound of Silence." Without saying a word of introduction, he then drew it out, fingered a few decoys and finally gave himself over to the iconic first verse.

And so back to Gill, who gestured around the stage as he tried to lighten the mood: "Every one of them called me and said, 'We'll come, but you have to follow him.'" That tone — playful yet reverential — carried the entire two hours.

"This is a typical thing in Nashville," Paisley later explained. "On any given night there's 10 of these." When he then asked Simon if that's how it was in the Greenwich Village folk scene, he earned some good-natured ribbing for his use of the phrase "back in your day."

Over the course of the night, Gill played "Whenever You Come Around," "Go Rest High on That Mountain" and a new tune that particularly impressed Simon. Simon, meanwhile, continued with "Me and Julio Down by the Schoolyard" and "The Boxer," and sent everyone home with the Everly Brothers' "When Will I Be Loved." After complimenting Gill, he laid into the guy that had brought up his age: "Brad, I didn't like any of your stuff."

Underwood told Simon about the time she earned her grandparents' ire for singing the "making love" line from "Cecilia" as a little girl, and she helped her CMA co-host through their duet "Remind Me." As it turned out, he needed it more on "Welcome to the Future," forgetting half the Obama tribute's second verse. For Paisley, it was a bit of a full-circle moment: Harris had just finished a song about Emmett Till, and with the Hall of Fame still on his mind, he spoke about how simple songs can communicate big ideas.

"I was in Times Square in 2008, when the election was, and struck by the amazing way that after electing the first black president we had all these people in the streets," he said. "Sometimes in Nashville, we're so surrounded by music that sometimes we forget that it can say something really important."