Since his ascension, the hardworking singer has embarked on major headlining summer shed jaunts, the latest of which, "Margaritas and Señoritas," supports 2002's No Shoes, No Shirt, No Problems. A year old, the album continues to spit out hits, including the aforementioned "Big Star" and the equally pop-influenced "Young" and "The Good Stuff." Chesney's been named the Academy of Country Music's Top Male Vocalist for the year and decreed as People's Sexiest Country Singer Alive.
Chesney, listed as trade magazine Pollstar's No. 1 ticket-seller for the first quarter of 2003, has been known to pull guest stars out of his pocket for his live shows, including Indianapolis Colts quarterback Peyton Manning, who's even stepped onstage and played simple guitar chords. Backstage, Manning taught Chesney, a University of Tennessee fan, a thing or two about passing. Not that the big guy needs any training in that area or anything.