Performing at the White House is sort of a rite of passage for megastars. After all, not just anyone gets invited to entertain the President of the United States. The invite came from George Bush Jr. in 2006, when John Howard, the Australian Prime Minister, was set to come for a visit. Bush really wanted to impress him, so he set up a private concert with the country star in the East Room. As if performing for such an elite crowd wasn’t cool enough, when he got done singing, Bush gifted him with a custom-made pair of eel skin boots made by Rocky-Carroll.
Of course, it wasn’t just any custom pair. The details on the boots were commemorative of the evening and featured both the U.S and Australian flag. Two years later, Chesney came back to the W.H to perform the National Anthem for a special tee-ball game.
Got in a Brawl with Police (and Tim McGraw)
Yep, you read that right. People can say many things about Kenny Chesney and his life but they can’t say he’s boring, that’s for sure! Fans got more than they bargained for when they went to see Chesney and McGraw perform at the George Strait County Music Festival in New York, back in 2003. After they had delivered the opening performances for the show, Chesney jumped on top of a horse – one that happened to belong to one of the deputies working at the concert.
The deputy shouted for him to freeze as he started to ride away. But before he could make it very far, another deputy came out and physically started to remove him from the horse when Tim McGraw jumped in and saved the day! Man, that would have been well worth the ticket price of that concert to see all of that go down.
Jumped the Gun
In 2016 at one of his concerts in Philly, Chesney had a blooper moment that revealed some sad (and false) information. The country music star announced to a crowd of about 70,000 people that Officer Christopher Dorman had passed away. The Delaware County police officer was shot 7 times by a drug dealer in the line of duty, including a shot to his face. He was scheduled to attend the Chesney concert but obviously couldn’t make it due to the fact he was in the hospital recovering.
But instead of making that announcement, the singer told his fans he had died. After the Delaware County Police Department saw what had happened, they took to social media to correct him and he ended up calling the officer after the concert to make his amends. He also invited him out for some beers when he was up for it.
He Performed Live with Reese Witherspoon
It makes sense that everyone would want to see Reese on stage with Kenny Chesney. After all, she’s pretty much the perfect Southern belle. The actress attended a charity auction in her home state of Louisiana, thrown at the House of Blues by none other than Matthew McConaughey. During the event, one high roller threw down nearly $30,000 for a once in a lifetime chance to see Witherspoon jump on stage and sing along with the country star.
The performance was a huge hit with the crowd, who didn’t seem to mind that she didn’t exactly remember every lyric to the jam! The auction was created to support McConaughey’s non-profit organization dubbed: Just Keep Livin. The two stars performed their rendition of Johnny Cash’s hit song Jackson.
He’s Got a Huge Team Behind Him
It’s not unusual for celebrities to have entire entourages to support them through their hectic lives, and Chesney’s no different. But when you hear the word “entourage” you probably imagine a team of around 20 or so people. In Kenny’s case, it’s more like 120 people. The singer spends nearly all of his time on tour and is constantly on the move, having somewhere to be and something to do. So, he’s got a team member for pretty much everything. But don’t feel bad for his employees, because Chesney treats them with the utmost appreciation.
After each and every tour, he takes the whole team on a getaway for a week so everyone can relax. He also gives one lucky team member the profit from merchandise sales, which he chooses with a special lottery he made just for the occasion.