10 Things You Didn’t Know About Kenny Chesney: No. 5

5. Working for Kenny Chesney has its benefits.

Kenny Chesney takes care of the several hundred people he employs ever year. In the past, the singer has cut $14,000 checks to each member of his road crew and run a "merch" lottery, in which everyone's name goes into a big hat and the person whose name he pulls out gets all the money from that night's merchandise sales. "Probably the biggest check was $300,000," he told the New York Times in 2011. A yearly tradition is an all-expenses-paid trip to the Virgin Islands for everyone on his crew, plus their families. Needless to say, turnover is low amongst his employees!