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Five Country Stars That Are Licensed Pilots

By Nancy Brooks // Country Writer, Beasley Media Group

Country stars travel all over the country throughout the year to play shows for fans, and many of them fly in their own private lets.

Chris Young, Jason Aldean, Brad Paisley, Reba McEntire, and many more have purchased their own planes to make the touring life easier for them and their families so they don’t have to stay away for so long. Reba has been flying private since the early 1990s and even got some flak from her Music Row neighbors when she wanted to put a helipad on her office roof near downtown Nashville. Music Row tenants were concerned that the helicopter noise would disrupt recording studios.

Many country superstars are taking their love of private flying one step further, getting their pilot’s licenses and flying themselves to and from shows.

Thomas Rhett has been thinking he would like to pilot his own plane for years but admits he has reservations. Rhett told us, “I could definitely see me still wantin’ to do that. I have so many pilots in my family. My brother-in-law, Grayson, is a pilot, my father-in-law is a pilot, and a lot of my close friends are pilots. I think it would take a little more trust on my own end to trust that I could do it right. I’m not the most attention-to-detail person, and I feel like you really need to be detailed to be a pilot.”

He added, “So, I don’t know. Maybe I’ll become a very detail-oriented person over the next five years and decide that getting my pilot’s license is something I’d wanna do. If Dierks [Bentley] can do it, I can do it.”

The FAA requirement to become a private plane pilot requires 40 hours of flight training time for the private pilot certificate. Many new pilots have 60-70 hours.  But many country stars have done it and now are able to fly their own airplanes.

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  • Alan Jackson

    Country Music Hall of Fame member Jackson was flying to and from gigs early in his career and learned how to fly by watching and learning from the pilot. He told us, “When I started flying to work, I got interested in watching the pilot who flew me, and he taught me. At that time, we had a farm with a pretty big grass strip, and I had a plane with amphibious gear so I could land on water, the lake. I just kind of flew around Nashville. I still have my license; I just don’t fly. Denise (his wife) got tired of my flying and worrying about me.”

    Alan Jackson wearing a plaid shirt and cowboy hat on stage playing the guitar
    Rick Diamond/Getty Images

  • Dustin Lynch

    In August of 2022, Dustin revealed on Twitter that he got his pilot’s license. He wrote in a post, “Set a goal, and when you get there…man, it always feels good! First solo flight today.”

    Dustin Lynch on Twitter: "Set a goal, and when you get there...man it always feels good! First solo flight today 👨🏽‍✈️🛫 / Twitter"

    Set a goal, and when you get there...man it always feels good! First solo flight today 👨🏽‍✈️🛫

    Lynch told us it was a new hobby. He said, “What really pushed me was we weren’t touring. So, it was like, ‘Let’s pick up a new hobby.’ I have some farms that are hard to get to – driving or flying commercially.”

    He posted a video of attending an air show with his friend Swiss to Instagram at the time.

  • Luke Bryan

    Luke told us in 2021 that his new passion is something he started to learn during the pandemic when he purchased a helicopter. And he is a licensed helicopter pilot. He said, “I think that was a big reason why I wanted to learn, and if I’m looking at all these gauges and I know everything is going smoothly, you know it’s just something fun.” Luke also can now compare flight logs with his buddy Dierks Bentley. He offered, “I’ve always had a little envy of Dierks Bentley. Dierks and I have this intellectual competition going on where he can’t out-intellect me. Dierks is like savant smart, so I like to try and challenge my goofy savant smartness against his. So we’re both aviators now, and he can’t one-up me in the aviator game.”

  • Tim McGraw

    Tim is a trained pilot and flies to and from concert dates. His wife Faith Hill and he have a deal never to fly together privately in case something happens so their girls will not lose both parents. He’s been flying for years. In a recent promo for Cirrus airplanes, McGraw says the thing he loves most about flying his own plane is the “relaxation of it.” He added that he loves being up in the air, not having to think about work or “any of that stuff.”

  • Dierks Bentley

    Dierks is one of country music’s most well-known pilots. He flies his own Cessna plane to shows nationwide. His tourmate Jordan Davis recently told us that Dierks saved him recently and helped him make a show.

    Davis told us, “First show of the tour, I’m sitting on an Air Canada flight plane in Toronto. It’s an hour delayed. So I was like, ‘This flight is gonna get canceled; I’m gonna miss the first day of the Dierks tour.’ Then I get a message from my manager that says, ‘Hey, get off the plane; Dierks is gonna re-route and pick us up.” Jordan continues, “True story. He swoops in and picks us up with caked-on sunscreen in his Dierks gear: flip-flops and shorts. I was like, ‘Thanks, dude, for picking me up,’ he says, ‘Yeah man, hop in, we’ll take off.’ We fly to Canada going down to land; something’s on the runway, and we have to pull back up. Dierks is flying the airplane, not like co-piloting; he’s flying the airplane, goes down, pulls back up, circles back around, comes in, and in one of the smoothest landings I’ve ever had in a PJ (personal jet).”

    A couple of years ago, Bentley did a flight safety video.

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