Whitney Pastorek
June 12, 2009 AT 04:00 AM EDT

For each of the past five years, party-loving country superstar Kenny Chesney has played for more than a million fans, making him one of the biggest concert artists of the decade. We caught up with this year’s mega-tour at Pittsburgh’s Heinz Field, where Chesney performed on June 6 for 47,000 fans. The production is massive — 32 trucks are needed to transport the stage and equipment — and it’s staffed by old friends with a common goal: Spread good vibes. For Chesney, 41, it’s the culmination of a dream that started in Johnson City, Tenn., 19 years ago. ”We were at a Laundromat my senior year of college, when I started playing bars,” he says. ”David [Farmer, now his road manager] said, ‘Wouldn’t it be cool to have a song on the radio and go out and play, just to see what it’s like?’ This is our 16th trip. Not many people get 16 trips around the sun. We don’t take it for granted.”

(1) Dozens of boats are docked in one of the three rivers adjacent to the stadium, many having arrived the night before. The afternoon of the show, Chesney — a huge fan of boating culture — heads out to join his people. ”This is where it’s gonna get fun,” he says from the front of a golf cart flanked by jogging security guards and increasingly hysterical fans. Upon reaching the tailboaters, he climbs aboard a craft and performs a surprise sing-along. ”Kenny’s on my boat!” screams the woman whose vessel has been pirated. ”I love you guys,” Chesney tells the assembled mob.

(2) ”I’m constantly thinking about connecting with people,” Chesney says. ”Before every stadium show, I go up to the top and sit in the very back row. I want to see how far I’ve gotta go.” So how does he reach the guy in row Z? Chesney points to his six video screens, then toward his eyes, making a V shape with his index and middle fingers. ”Laser beams.”

(3) Fans party in the parking lot, bringing kiddie pools, grills, and cooler after cooler of beer. When asked if he feels a duty to encourage responsible choices, Chesney doesn’t blink. ”They’re grown-ups, most of ’em,” he says. ”I’m not their mother. It’s just a concert.”

(4) The legendary Chesney party aesthetic is in full force after sound check, when he gathers with his crew at the ”Annex Bar and Grill,” a stand behind the stage that dispenses hot dogs and beer at all hours.

(5) To make a grand entrance at the beginning of the show, Chesney is smuggled through the audience via road case to a tented area from which he will fly to the stage. It’s a private moment; Chesney uses it to get his superstar on. ”This is where I turn into Him,” he says as he’s rolled out (yes, he invited EW along in the box). ”It’s where I say, ‘This is why you’re here. This is where it starts.”’

(6) Showtime! Chesney floats slowly over the audience, like the Wizard of Oz singing down from his hot-air balloon. ”I used to go to a lot of shows, and there was always this wall, this element of ‘I’m here, you guys are there, that’s how it’s gonna be all night,”’ Chesney says. ”I hated that.” Inspired by an old Van Halen video and the airborne cameras at NFL games, he came up with the flying chair, from which, he says, the crowd looks like ”the Horseshoe Lounge in Johnson City, Tennessee…times 10 million.”

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