Meet Grayson Taylor, a Dallas Pilot Who Wants to Interview Bands in the Sky

Resting between sets at a raucous SXSW party, Grayson Taylor looked like he had something to get off his chest. The multitalented 24-year-old makes a living as a flight instructor at Aviator Air Flight School in Grand Prairie and spends his nights in the music scene as one of the city’s most talented concert photographers. Case in point, if Taylor has an idea, you best listen.

He pitched a total curveball: a YouTube talk show where he flies touring bands to their Dallas date and interviews them in the sky.

It’s hard to find an easier sell than that or a bigger logistical nightmare.

Our reaction was simple. Amazing idea, call us if you ever figure out how to actually do it. We meant that, but we didn’t expect him to call so fast.

Just two months later, Taylor had secured a date in the sky with Austin-based band West 22nd, who were embarking on their first nationwide headlining tour. On May 18, West 22nd’s The Nowhere to Be Tour traveled from Houston to Dallas for a performance that evening at the Cambridge Room at House of Blues.

It was in that same room that Taylor first saw the band in April 2024. He was shooting for the opening act, Red Wall, a criminally unsung Dallas band. When he first saw West 22nd, their joyful brand of college party rock was infectious.

It’s emblematic in the band’s most-streamed track, “Sunburns,” which evokes that hazy sort of feel-good flavor that permeates the Backseat Lovers or Flipturn.

“They’re electric on stage,” he says. “They bring so much energy to a crowd. This is all pretty Texas-based, and the fact that they’re a band from Austin and I was able to pick them up between Houston and Dallas.”

Taylor briefly connected with the band and their manager following last year’s show, aligning the stars for them to be guinea pigs in his audacious new idea. On the morning of the 18th, Taylor flew to a small airstrip in Corsicana to meet the band formally.

“Immediately, everybody is cool,” Taylor recalls. “No awkward small talk or anything, they were just stoked to send off Logan and Jet.”

For this trip, Taylor manned a small three-seat plane that could only fit West 22nd’s lead singer, Logan Madsen, plus bassist and Dallas native Jet Beck.

“When I saw the plane I was freaking out,” Beck said. “I had imagined it before, but seeing it in person was different.”

The plane was very small, and it didn’t help that a plane of the same size was doing barrel rolls in the air before their takeoff. Luckily, Beck and Madsen pushed through and boarded the plane, where they spent about an hour in the sky and landed safely in Grand Prairie.

Madsen was the first to get out of the plane, immediately outstretching his arms, dropping into a series of push-ups and kissing the concrete tarmac beneath him.

“It was so effortless when he was flying it,” Madsen said about Taylor. “He even let me hold the wheel for a second while we were flying.”

Perhaps bonded by the experience, the three of them seemed like they could’ve hung out together on that runway for hours. But of course, they had a show to play, and took off for House Of Blues, where Taylor continued to film backstage and during the show, culminating in an awesome highlight reel of an unforgettable day.

“It’s cool the fact that it actually happened,” Taylor says. “That was the band that I wanted to take up for the first time.”

The full video, which is 13 minutes in total, was posted under Taylor’s “Cloud Club” YouTube channel. It covers the before, during, and after of the flight, plus behind-the-scenes footage of the band warming up and performing the show.

“It was insane, and he scared the shit out of me,” Madsen said to the packed house at Cambridge Room, recounting the day spent with Taylor. “I thought I was gonna die, but we made it here in one piece, so give it up for Grayson.”

Taylor hopes to continue the touring band flight series in the future. Who’s next? Who knows?

“It’s so much money to rent the airplane,” he says. “So if it does well and people want more, then it’s an investment and I’m willing to do it. I would love to, we’ll see how it works out.”