Photo via Kenny Chesney Facebook Page

They were hanging in the trees, crouching on roofs, standing on the far side of Duval when Kenny Chesney took over the Hog’s Breath for a stripped down, 3 hour Keg In The Keys show Sunday afternoon (3/3). The 4-time Academy of Country Music and 4 time Country Music Association Entertainer of the Year brought three players, some best loved hits, obscure album tracks, a few well-chosen covers and special surprise guest, songwriter Keith Gattis, who helped perform “El Cerrito Place” and “I Am A Small Town” for the freewheeling acoustic show.

“When it gets to be about time to get back out there, I really like to do these surprise shows,“ Chesney says. “It’s a low impact way to ease back into the songs, to find the curve in what we do – and have a whole lotta fun doing it.”

Low impact for the man slated to play 19 stadiums on this summer’s No Shoes Nation Tour which kicks off March 16 at Tampa’s Raymond James Stadium, means about 5000 people crammed onto the patio, in the streets, belly-to-belly inside the bar and on the sidewalks around the iconic Key West watering hole on Front Street.

After laughingly announcing, “We’re gonna play some old songs, some new songs and a whole lotta songs,” the Luttrell, Tennessean launched into “Welcome To the Fishbowl,” the ironic song about our obsession with fame. With a few churchy piano rolls from Wyatt Beard and a burning lead from guitarist Kenny Greenberg, it was obvious Chesney had come to play. The fans, some of whom had waited outside overnight, were thrilled.

Joking that he’d not had a beer since the first of the year, Chesney apologized to the crowd for “needing to be a good boy, and this is the worst place in the world to do that.” Instead he gave them an industrial strength helping of classics including “Summertime,” “You & Tequila” and “The Boys of Fall,” as well as obscure gems like Guy Clark’s “Hemingway’s Whiskey” and “On The Coast of Somewhere Beautiful,” which Chesney admitted was a true story “and she lives up in Jupiter, Florida.”

Talking to the crowd about where they’re from and even inviting two sisters – and their Mom! — onstage to sing with him, it was a loose afternoon swapping songs and stories with people who felt more like friends than fans. In keeping with the ad hoc feel, guitarist Clayton Mitchell took lead vocals on Steve Ray Vaughan’s “Pride & Joy” and Van Halen’s “Ice Cream Man,” while No Shoes Radio’s Mark Tamburino romped through Violent Femmes’ “Blister in the Sun,” as well as Chesney good-timing through George Strait’s “Ocean Front Property” and Merle Haggard’s “Think I’ll Just Stay Here and Drink.”

“I opened my very first real headlining show in West Palm, so Florida’s become a part of my soul,” Chesney explains. “When we were trying to figure where to do this year’s Keg show, nowhere in the continental United States has the spirit of what Life On A Rock (his upcoming April 30 release) embodies quite like Key West. Starting another year, it seemed like the only place to do this show was the Hog’s Breath.”

Introducing “Pirate Flag,” the insurrection anthem that marked his 8th Top 25 debut, Chesney proclaimed, “This is a song a little bit about rebelling, about rebelling against anything that’s mundane in your life.” Fans raised their glasses and No Shoes Nation skull and cross bones in the crowd, and sang along like it was the declaration of their life.