He's been watching it while singing a song during a rehearsal for his "Goin' Coastal" tour and it just doesn't snap. He gives instructions over the sound system to personnel at the back of the warehouse space where Chesney and his crew have been at it for several weeks.
"I want the picture to change every time he hits the snare drum - BAP! BAP! BAP! BAP! BAP!" he says while air hammering an imaginary kit.
A little later, his seven-piece band stumbles a bit and Chesney tells the group, "We've got to get that intro down." He worries over what he's going to say to the crowd at certain key moments, crafting and discarding drafts as he goes. "I'm glad you're here. You can help me with this," he tells a small group of record label executives and media.
This is Chesney in lock-down mode. With just a few rehearsals left till his tour kicks off Thursday in West Palm Beach, Fla., Chesney was agonizing over every detail.
"There's a lot of mixed emotions for me right now because I'm for the first time seeing everything we've worked so hard on come together," Chesney said. "And I'm very happy about that. But on the other hand it's not all together yet so it's the thing that keeps me up at night when I'm preparing to do this."
The attention to detail is what has made Kenny Chesney one of the most bankable acts in the touring business, regardless of genre. Since 1999, Pollstar figures show he has sold more than 8.8 million tickets and grossed more than $460 million. Only the Dave Matthews Band has sold more tickets over the last decade and only Matthews and Celine Dion have grossed more.
Chesney took the year off the road in 2010 to concentrate on his lauded new album Hemingway's Whiskey and to make three films - a 3D concert movie and two documentaries about football. With his return to touring, he's bringing along Uncle Kracker and Billy Currington to open his arena shows; the Zac Brown Band will join them on11 stadium dates throughout the summer.
Currington's beachy vibe is a lot like Chesney's, but he's never experienced anything like the "Goin' Coastal" tour before. He's trying to raise his game to keep up with country's biggest draw.
"We actually had to bring in a little more production than we're used to," Currington said. "It's a new experience for me playing places that big and needing this much gear."
Chesney says this year's show will be leaner than previous productions.
"But I feel like it's better," he said. "I feel like musically it's better and that visually it's really, really good and we've been working on that a long time. So it's very exciting to get to do what I love to do again, you know, and to feel that energy and to be that person up on stage. It's an unbelievable feeling to feel all those people focus energy right on you, and us as a band we can feel that. There's no feeling like that anywhere."