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Pilot Bentley Ready to Rock Oshkosh

July 19, 2015 - Having Dierks Bentley perform in EAA AirVenture Oshkosh’s opening day concert Monday night is unique in a number of ways. He represents the first contemporary country, non-rock legacy act to perform at the opening day concert; plus he’s the first country singer to appear on the Main Stage at Boeing Plaza, presented by Ford Motor Company with additional support from Cirrus Aircraft.

Oh, and he’s also the first private pilot to open the show—an instrument-rated pilot to boot. What’s more, he flew into Wittman Regional Airport yesterday in his custom Cirrus SR22T Xi. And that makes Bentley extra special in the eyes of many EAA members, regardless of what type of music they prefer.

“I’m so glad to be able to carry the torch for both aviation and country music at Oshkosh this year,” he said about a week before launching his Sounds of Summer tour in May. “We’ve been trying to get this tour out the door. By the time we get to EAA we’ll really be rockin’!”

He became interested in planes the way many of us do; gluing models together.

“I just always had model airplanes as a kid,” he said. “My dad and I would glue them together and I would hang them up in my room.

He took a Discovery flight at age 13 in Phoenix—his hometown.

In 1994 when he was 19, Dierks moved to Nashville to chase his country music dreams. He had a friend who was also interested in flying, and they both began taking flight training at the Cornelia Fort Airpark. Within seven hours he had soloed, then after a move to Smyrna, Tennessee, he completed his training and passed his checkride in 1997.

Focusing on his career and lacking a flight mission or goal, flying took a backseat for awhile, he said, until about 2010.

“I was playing a gig in Hazzard, Kentucky, when this little plane flew overhead,” he explained. “Someone said, ‘Hey that’s Tim McGraw,’ and I said, ‘What?’

“‘He’s got his pilot’s license.’ ‘Really?’”

Bentley eventually got a hold of McGraw who introduced him to someone who put him in touch with Cirrus Aircraft. That led to an opportunity one night after a performance to give flying to the next tour stop a try instead of riding on the tour bus.

“So we flew to Indy,” he said. “Now, if you look at my logbook you see that 15-year gap, then boom! Once I did that first flight (to Indy) and discovered this whole world opening up to me, how many airports are out there in this country, and how extremely close they are to the places I play…From there forward most of my training involved going to a show. Or coming back from a show that night.”

He was hooked. Bentley is now owner-operator of his own Cirrus and flies about 250 hours a year–with about 700 overall since 2012.

He and his wife, Cassidy, have three kids, Evie, 6, Jordan, 4, and Knox, almost 2, and one of the toughest aspects of life on the road is being away from family so much. Having the ability to fly his own airplane has changed that equation.

“The plane saved me on average of 60 extra nights and mornings a year, where I can make pancakes, take the kids to school - it’s a complete time machine,” he said.

And that has not been lost on members of his band, who have been eager to snag a ride with the boss when offered. “Everyone on that stage has told me they’re all new aviation fans,” Bentley said. Usually it’s all about kids. Whoever has the most kids to get home to gets priority. “Have another kid, and you have a better chance at a seat.”

When he went to Duluth, Minnesota to pick up his airplane, Bentley was impressed by the company. “Just great folks working there,” he said. “Got the chance to walk the floor and meet Mary, who does the flaps, others working on the gear, just awesome to see those folks. I’ve been there a couple of times now, and before we fly into EAA I’ll head up there again to visit and check out the G5 (Generation 5) SR22.

Bentley has secured a delivery position for the Cirrus Vision jet. “I’m excited about it. I love a propeller, one day I’m flying by myself, one day I have three kids in back and I am playing the role of pilot and in-flight entertainment, hostage negotiator, beverage and food director, entertainment director.

“Moving on (to a jet) will be a different beast, but then again studying for the IFR is one of the most enjoyable things I’ve ever done, learning-wise,” Bentley said. “It was fun to realize my brain could still do math after all those years trying to write country songs. Out on the road, using Gleim textbooks, really enjoying the process. I’m sure it will be the same transitioning to the jet, and I’m sure I won’t look back. But I do love the SR22. What a great plane.”

The other types of planes he’s been in include a Pitts (Bentley was excited to learn about the 70th anniversary of the Pitts celebration at EAA AirVenture this year) a Cessna Mustang, a Beech Baron G58, and a floatplane, which he really enjoyed.

“It was a 1946 Piper seaplane we flew, yankin’ and bankin’ down a back waterway in Canada. Awesome,” he said. “You will see footage of that at the concert.”

This will actually be Bentley’s second visit to the annual Oshkosh convention. Two years ago he snuck in and snuck out to perform at Cirrus’ annual media event held the Sunday before opening day. That’s also where the seeds were planted that brought him here for this year’s show opening concert.

“I told them I’d love to come spend some more time here, but it’s summertime, and we’re on the road,” Bentley explained. “I told them the only way to get me back here is if you book me. And they worked really hard at it and here we are, coming back for a gig on Monday, that’s perfect. I’ll also get a chance to hang out a little bit.”

We asked what it will be like to be on stage at Oshkosh looking out over the Boeing Plaza and seeing so many magnificent airplanes like the B-52, B-29, F-35, F-22, and the list goes on.

“I’ll probably be looking back at the drummer, who is also a pilot and even more of a plane nut that I am,” he said.

As for Monday's concert, Bentley’s raring to go.

“It’s up-tempo, a lot of energy, couple of moments where we talk about some serious stuff, but otherwise, we like to party, man. Get on stage and hit it pretty hard, let people forget about whatever problems that (they) might have for a while. I hope to contribute to that great vibe, celebration of good times, and aviation and the community.

“Personally, I love being a pilot, love being a part of the aviation family, and am really looking forward to meeting new folks, Bentley said. “It’s a great connection, meeting another pilot, since you probably have 75 percent of things in common, no one really cares what you do in your other life, all they want to do is talk about planes.

“It’s kind of a nice thing for me to be around people who don’t really care too much about the music stuff, just want to talk about airplanes, so I enjoy that.”

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