Or at least, he did date a beauty queen at one point. In 2008, the musician went public about his relationship with 24-year old Amy Colley. The younger woman was a nurse at the time they met, but she was also Miss Tennessee back in 2005. One source who was close to Chesney reported to Star Magazine that when the two were together, Chesney was head over heels for her.
Things actually got so serious between them that he even met the former beauty queen’s parents, when he took a trip home with her for Thanksgiving and he brought her home to meet his family as well. But that wasn’t the only trip they’d take together. They were later seen together in several exotic destinations, cuddling and kissing on the beach.
But He Also Allegedly Cheats on Beauty Queens
Just as Kenny got together with Amy when things started to get rocky with a former relationship, so the cycle continued. Of course, Amy thought they were still an item when the country star was seen in Cancun with another woman, but she was in for some heartache when she heard her former beau was vacationing with someone else. It wasn’t just any other woman, though. It was Jenn Brown, the very first female Inside the NFL correspondent from ESPN.
One witness reported that the two obviously looked like they were touching each other constantly and “definitely looked like more than friends.” A heartbroken Colley had had enough at that point, and the two ultimately ended things. As far as the other girl, nothing ever got too serious with Brown.
Living La Vida Bachelor
Country artists tend to sing about love a lot and Chesney’s songs about having loved and lost and loved and lost again, and again...they’re all pretty much right on the money. Chesney has been in his fair share of relationships over the years. But relationships aside, he’s actually copped up to having slept with over 100 different women.
The star told Playboy that he prefers to live that way and that if he had to be stuck in a “regular” relationship with a wife and kids that he would very likely “blow his brains out.” But that doesn’t mean he never gave it a try at one point in his life…
Got Between 50 and Kanye’s Beef
Kanye West and 50 Cent have a little friendly competition going on that’s lasted for, oh, pretty much as long as they’ve both been in the music business. The beef stems from them fighting for the title of the King of Hip Hop. 50 was making his traditional rap and Kanye West came in with a mix of hip hop with a more pop vibe and his albums flew off the shelf. So, the rappers decided to have a little contest back in 2007. 50 dropped his album, Curtis, on the same day that Kanye released his album, Graduation. 50 Cent told everyone that if Kanye sold more CD’s than he did, he’d retire from the game altogether.
Just when the feud couldn’t get any more interesting, Chesney popped up in the middle of it and released an album of his own that day. But since he was a little late to the party, he wound up in third place behind Curtis in 2nd and Kanye with the gold.
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.