Last week we learned that TAYLOR SWIFT takes every single employee of her tour on an exotic vacation when the project wraps.  But she's got nothing on KENNY CHESNEY.  He does that, AND he gives them a chance to win over a quarter of a million dollars.

Kenny tells the "New York Times",

At the end of each year, I take the band, crew, the merchandise people, catering people, my management team, their wives, girlfriends, whatever, down to the Virgin Islands for a week to thank them.

I pay for everything, and we've done it every year since 2002.

And here's the part about the money.  He continues,

I want all the people out there who work with me to feel as appreciated as possible, especially the people who are the first to get up in the morning and the last to go to bed... my crew guys.

Sometimes we do a 'merch lottery'.  We put everybody's name in a huge sombrero and whoever's name I pull out gets all of the money from merchandise sales for that night.

Kenny was asked how much money could that be.  He answered,

Probably the biggest check was three hundred grand.  But do you know what those guys did?

This is why I think this kind of thing works:  They waited until the end of the year and I wrote one big check to the crew and they divided it up 13 ways.  Doing things like that just motivates people.