9 Things to Know About Kenny Chesney

His mom gave birth to him when she was 19

Chesney's mom is a hairstylist named Karen who gave birth to him when she was 19 and was divorced soon after he was born. His dad, Dave, is a former schoolteacher. Karen divorced a second time when Chesney was in high school and had recently married for a third time when her son spoke to Parade in 2010.

"She was dating someone once and broke up," Chesney recalled of his mom. "And this stayed with me. She said, 'Kenny, I just want you to know I'd rather be miserable alone than miserable with somebody else.' That makes a lot of sense to me."

His favorite good is grilled cheese

While the star follows a strict diet, he allows himself a cheat meal on Sundays, and it's likely the one day of the week he eats his favorite food, grilled cheese. "I love it," he told PEOPLE in 2010. "Just a plain grilled cheese with extra salt. I wrote a song called 'Red Wine and Grilled Cheese.' I'll put it on a record some day."

His baldness no longer bothers him

While Chesney is nearly always photographed with a cowboy hat on, he's bald underneath the accessory, something he had to learn to accept early on.

"When I was 17 or 18, I'd take my helmet off on the [football] field, and I'd see hair in it and go, 'Good God! What's going on?'" he told Parade. "It did bother me in college a little bit — going bald — but it doesn't at all now. What's ironic about it is that friends of mine in their 30s and 40s are just starting to lose their hair and are freaking out. I went through all that in high school."

He went to school for advertising

The "Big Star" singer studied advertising at East Tennessee State University, where he began his music career by playing in local clubs. His first gig paid him $5 an hour along with free enchiladas. "When I was playing for tips in college, I felt a fire in my soul," he explained to Parade. "I had the same principle of focus that I had learned playing football."

He was arrested in 2000

Chesney and Tim McGraw were arrested in 2000 after headlining the George Strait Country Music Festival near Buffalo, New York when Chesney attempted to ride away after mounting a policeman's horse and McGraw physically held back the officers trying to stop him. McGraw's manager Mark Russo was also involved in the incident.

McGraw was charged with second-degree assault, obstructing governmental administration, and resisting arrest, his manager had four minor charges and Chesney was charged with disorderly conduct. All three men went to trial the next year but were acquitted on all charges.

He doesn't eat carbs after 5

Chesney's passion for fitness is well-documented, and that extends to his nutrition. In a 2016 interview with GQ, the singer opened up about his healthy lifestyle and revealed that one of the things he does to keep his fit figure includes not eating carbs after 5 p.m.

"I load up on carbs early," he said. "I don't eat any after 5:00, whether on or off the road."

Chesney added that his healthy lifestyle sometimes gets in the way of his social life. "I'm an emotional eater. We all are. I was brought up not eating this way. And when you have that kind of focus on your diet, there's no social life," he said. "Your friends, your girlfriend, everybody wants to go out and have drinks. But when you're on this kind of specific diet, you look kind of weird when you go to a restaurant and bring your dinner with you, because it has to be measured."

He was supposed to be in New York City on 9/11

The Tennessee native was supposed to be just around one block from the World Trade Center on 9/11 shooting a music video for "The Tin Man," but equipment delays pushed the shooting date back.

"It didn't hit me at first. I was laying on the couch, just watching this and couldn't believe what I was seeing, and I thought, 'Oh, my God.' I said, 'We're supposed to be there,'" Chesney told CMT.com. "And it was a weird feeling. You know, I've always believed in guardian angels, but it really makes you believe that there's something up there."

He is a clean freak

"I am a clean freak," he told PEOPLE. "I take three showers a day. I can't stand to be sticky. I'm a bodywash guy. It freaks me out to use soap."

He might be obsessed with cleanliness, but Chesney's worst habit is biting his nails, admitting, "I've done it ever since I was a kid, and I've tried everything except hypnosis to stop."

He wanted to be a football player

Like several of today's country stars, Chesney had his sights set on a sports career before turning to music. He played football in high school and wanted to continue with the sport, but his 5'8" frame was a hindrance.

"It all started for me on that field," Chesney recalled to Parade. "Football taught me how hard you had to work to achieve something."