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Yes, Cole Swindell Has Flown With Dierks Bentley — and It Was Awesome

Cole Swindell Dierks Bentley friendship
Ethan Miller, Getty Images

After opening for major country names such as Jason Aldean and Florida Georgia Line, Cole Swindell is spending most of 2017 on the road with his musical idol, Dierks Bentley, as an opening act on Bentley’s What the Hell World Tour. For Swindell, who’s “been a fan [of Bentley’s] since the beginning,” it’s the perfect opportunity for both himself and his band and crew to learn from one of the best.

“It makes me proud to know my guys — not just me — my band, my crew, are out there learning from all of them,” Swindell shared at a recent media event. “It’s just cool to be out there, me and [Jon Pardi], watching, because it’s still like Day One for me out there, and it is for him, too.”

Swindell — whose current single, “Flatliner,” is a duet with Bentley — is so close to his tour boss that he was once invited to fly in Bentley’s private plane with him. It’s a memory that Swindell cherishes — but doesn’t necessarily plan on repeating.

“I’m not a big fan of the smaller planes, but one time, [when] we shot the video for “Flatliner,” we were in South Dakota, [and] he asked me to fly back,” Swindell recalls. “It was just a cool, cool thing to get to fly with him; we actually hung out. He had a pilot that helped, but he made me sit up there: He said, ‘To know me is to fly with me. Get up here.’ So he let me sit in the cockpit, and I got to take off.

Country Stars and Their Famous Friends

“I’ve never had a [flight] like that in my life. It just looked like we were at the end of the world. It was unbelievable, the view up there,” Swindell continues. “I still am not interested in getting my pilot’s license and flying, but it’s convenient. I hate traffic, so this flying thing — I could see how people get hooked on it. Just, the freedom of being up there; that view was unbelievable. I appreciate Dierks letting me fly along, [but] I’m not going to get spoiled. That’s his plane; he worked hard for it.”

In addition to opening dates on larger tours, Swindell has headlined his own Down Home Tour for the past three years. That trek found the singer-songwriter playing in smaller venues, but he is planning on taking what he’s learned on the road with Bentley (and others) and transferring it to his own big-venue headlining show — someday.

“Of course, that’s a dream of mine, one day, to be headlining [major venues]. Maybe next year, maybe not. Who knows? Whenever the time is right,” Swindell confesses. “I don’t want to rush that, but the atmosphere out there is how I want it to be when I’m touring: It’s professional, but it’s fun, and it is people taking care of each other.”

For now, Swindell is content to let Bentley have top billing and make the most of the experience while he’s part of the What the Hell World Tour.

“I know Dierks appreciates having guys who are still fired up and loving what they’re doing,” Swindell shares. “Dierks is as good as it gets as an artist and a person.”

A list of all of Swindell’s upcoming shows is available on his website.

How Well Do You REALLY Know Dierks Bentley?

NEXT: Cole Swindell Discusses His Friendship With Florida Georgia Line

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