Chesney got his start playing at small venues around his college campus in Tennessee. Before he had compiled enough original songs to put out his own album, he used to play covers for tips in bars. He would put the tip jar next to the stage and take requests, with a sign taped to the jar that said something along the lines of “tips appreciated.”
But apparently, he’d been asked one too many times to play “Freebird,” because the sign also made sure to include the fact that any requests for Jimmy Buffet, Freebird or James Taylor would cost the requestor $25. After he graduated, he moved to Nashville where he played in some larger venues and was eventually scouted by a recording studio.
He Wants a Hippy at Heart
He may be a millionaire and a clean-freak, but he’s looking for a woman who’s a little more carefree. In his song, “Wild Child,” he sings about his ideal type of girl. His perfect partner is apparently someone who’s got a lot of love but doesn’t care too much about shopping and trivial things like keeping her hair and nails done. And of course, as someone who loves himself a big old, greasy grilled cheese sandwich, he also wants her to love to eat just as much as he does!
He’s said during interviews that he wants anyone he dates to be intelligent and have a free-spirit. So basically, he is looking for an educated, cheeseburger loving Bob Marley fan.
He Made P!nk a Little Bit Country
P!nk isn’t really known to sing country-style songs, but rather her edgy, pop/punk style that’s taken her to stardom. She grew up in Pennsylvania and had a much different upbringing than the country star. But the two do share the fact that they both got into music at a very young age and worked their way up to where they are today. Over the years, Pink’s worked with some amazing artists, she even sang on the hit “Lady Marmalade,” with Christina Aguilera, Lil’ Kim, and Mya.
But in 2016, the musicians released a duet called “Setting the World on Fire,” in which Pink let’s go of her pop-style and tries out the country “twang.” Rolling Stone reports that the two singers are friends, and the prospect of the duet came up while they were hanging out in California.
Sleeping with Sara Evans?
Sara Evans and Kenny Chesney actually have quite a bit in common, at least, regarding their careers. They’re both hardworking country-music stars who are passionate about performing and creating. However, Evans got married and had 3 children, while Kenny went the bachelor route. Unfortunately, things between Sara and her husband Craig didn’t work out, and they went through a pretty rough divorce. In court, things got pretty nasty when they each pointed the finger at each other for sleeping around.
The singer’s lawyer brought up the fact that Sara was sure her husband was sleeping with their maid, while Craig shot back that she was surely having an affair with Chesney, among others. Kenny shrugged the whole thing off, saying they were baseless and nonsensical accusations.
After the future country music star graduated from high school in 1986, he started on his 4-year university degree at East Tennessee State University in Johnson City. He decided to focus his efforts on communications and marketing – something that would serve him very well through his career!
To keep his head above water while he earned his degree, he would play at various bars and other venues around campus. Chesney never forgot about where he came from throughout his superstardom. In fact, he continuously gives back to his community. He even helped Eastern Tennessee State raise nearly $30 million so they could have a sports field put in.