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A Brief History of Willie Nelson and Frank Sinatra’s Bromance

Ahead of Nelson’s tribute LP to his favorite singer, watch a series of surreal space travel PSAs they recorded in the early Eighties

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Chris Pizzello/Invision/AP/REX Shutterstock, Kobal/REX Shutterstock

On September 14th, Willie Nelson will release My Way, an album-length tribute to Frank Sinatra. While the concept of a Sinatra tribute LP isn’t new, Nelson’s approach is: He finds new, inventive ways to phrase songs like “Summer Wind” and “My Way,” both in his vocal melodies and with his famous gut-stringed acoustic, Trigger. “I learned a lot about phrasing listening to Frank,” Willie said recently. “He didn’t worry about behind the beat or in front of the beat, or whatever – he could sing it either way, and that’s the feel you have to have.”

The love between Nelson and Sinatra was mutual. Sinatra reportedly called Nelson his favorite singer after hearing Nelson’s 1978 album Stardust, where he sang classics from the American songbook. Though a career risk at the time, the album went quadruple platinum and set off a standards-LP trend that artists still try to emulate to this day.

Nelson was so big in the early Eighties, in part because of Stardust, that Sinatra even opened for him at Las Vegas’ Golden Nugget in 1984. “I don’t say that to brag,” Nelson wrote in It’s a Long Story: My Life. “Wasn’t my idea. It was [casino owner Steve Wynn’s]. He felt that since I was selling more records than Sinatra, I’d be a bigger draw and was entitled to top billing. I would have been happy with second billing … Sinatra’s my favorite singer.” The run didn’t last long: Sinatra canceled his appearances after the first night due to throat problems, although it became a music legend that Sinatra just didn’t like being an opening act. “That’s bullshit,” Nelson said. “Like me, Frank wasn’t hung up on being the headliner. He was the consummate pro.”

(Nelson’s former road manager Poodie Locke had another story from that time, which he shared in Joe Nick Patoski’s Willie Nelson: An Epic Life: “Frank loved Willie’s music,” Locke said. “But he couldn’t handle us [the crew]. We’re wearing Wranglers and we’ve got titty dancers backstage. It wasn’t his version of classy.”)

The same year as their Vegas gig, Nelson and Sinatra teamed up for another, more unexpected collaboration: to spread the word about the benefits of space travel. The Space Foundation recorded several of these PSAs in the early 1980s to spread the word about the “tangible benefits” of the space program, including digital imaging, which greatly benefited hospital treatment.

Sinatra and Nelson recorded at least two of these commercials, and Sinatra clearly gets a kick out of Nelson’s casual cool, beginning by pointing to his headband. “What do you call that, Willie?” Sinatra says.

“I call it ‘My Way,’ Francis.”

“Touché,” says Sinatra.

In another video, they detail a “medical system” that can be implanted, releasing medication automatically. “And I believe it’ll be the way to treat diabetes in the years ahead,” says Nelson. If you’re in the mood for a bizarre science lesson from two popular music giants, today’s your lucky day.

My Way is Nelson’s second release of the year, after the excellent Last Man Standing. He’s gearing up for a series of East Coast shows in early September, including a co-headlining show with Van Morrison at New York’s Forest Hills Stadium on September 12th and Farm Aid on September 22nd. We visited Nelson in his Texas studio around his 85th birthday earlier this year to find out what keeps him going. “I just enjoy playing,” he explained, “whether it’s on the stage, here in the studio, or wherever.”

In This Article: Frank Sinatra, Willie Nelson

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