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Willie Nelson Pays Tribute to Frank Sinatra

The country music legend puts his own spin on Ol' Blue Eyes' songs on his latest album

Willie Nelson
Willie Nelson and a well-behaved Trigger (photo: David McClister)

The genesis of My Way, Willie Nelson’s terrific new 11-track salute to Frank Sinatra, can be traced to Las Vegas circa 1978 when, so the story goes, impresario Steve Wynn introduced Sinatra to Stardust, Nelson’s landmark collection of standards. Wynn told Nelson and, according to Nelson’s longtime Nashville producer Buddy Cannon, “that’s how the connection began.”

Nelson and Sinatra didn’t actually meet until 1984, sharing the bill at Sin City’s Golden Nugget. Remarkably, Sinatra was the opening act. “I thought, ‘That ain’t right,’” says Nelson, “but he was a great guy who didn’t mind opening or closing.” That same year, they united for a pair of TV spots supporting the NASA-linked Space Foundation. In one, a tuxedoed Sinatra playfully derides Nelson’s comparative informality. Pointing to his bandana, Sinatra sneers, “What do you call that thing there?” Replies Nelson, “I call it ‘my way,’ Francis.’” A close friendship ensued. “I put it in one of my books that he was my favorite singer,” Nelson says, “and then I read somewhere that he said I was his favorite singer. That was the greatest [compliment] I could’ve gotten.”

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The actual shaping of My Way began with George and Ira Gershwin: specifically the Library of Congress’ prestigious Gershwin Prize, established in 2007 to annually honor a composer or performer’s lifetime achievement. When Nelson was named the prize’s 2015 recipient, he and Cannon hit upon the idea of an all-Gershwin album. Cannon’s first call was to keyboardist/producer Matt Rollings, inviting him to partner. “I knew he was the guy to make this record authentic,” Cannon says, “[and] Matt would know the exact right musicians to pick.”

To find such players, Rollings took his cue from pal Larry Klein. “I’m a big fan of the first Madeleine Peyroux album [Careless Love] Larry produced,” he says. The band on that disc is guitarist Dean Parks, bassist David Piltch, drummer Jay Bellerose, and organist Larry Goldings. “I knew Larry wasn’t going to play on [Willie’s] record, but I wanted everyone else. That was my model because that record rode the line between a jazz record and being very accessible as far as the grooves and harmonies.” Rollings stepped in on piano and added Paul Franklin, whom he deems “the greatest steel guitar player in the world.”


Notes Piltch, “Matt was looking for our aesthetic. He did all the arrangements [and] had a very specific idea of how he wanted it to be, so he was easily able to fit in [as pianist] because it was his imprint.” The result, Summertime: Willie Nelson Sings Gershwin, released in 2016, earned Nelson his 12th Grammy and first in the Best Traditional Pop Vocal Album category, edging out Barbra Streisand and Bob Dylan.

A trio of country albums followed, including Nelson’s tribute to another of his heroes, Ray Price, and Last Man Standing, a collection of songs co-written with Cannon. Then, refocusing on pop and jazz standards, “we were,” Cannon says, “originally talking about doing a record of Broadway showtunes. Willie kept saying, ‘Send me Frank’s version,’ so I said to Willie’s manager, ‘Why don’t we do a Sinatra album?’ We ran that by Willie and the idea took off.” Cannon again tapped Rollings, who reassembled Summertime’s sterling band. Befitting a Sinatra-themed project, Rollings selectively added brass and strings, respectively co-arranged by Chris McDonald and Kristin Wilkinson.

Nelson’s deep appreciation of Sinatra dates back, he says, “as early as age nine or 10. His music was everywhere. My sister plays piano and reads music, and everything that came out from Sinatra we wanted to learn, and did.” Fittingly, My Way’s playlist spans Sinatra’s entire career, from “Night and Day” and “Young at Heart” to “Summer Wind” and “It Was a Very Good Year.”


No Nelson album would be complete without two essential sidekicks: harmonica player Mickey Raphael, who masterfully weaves in and out, and Trigger, Nelson’s bruised and battered but seemingly indestructible guitar. “The triumvirate for making a Willie Nelson album,” Rollings says, “is Willie’s voice plus Trigger plus Mickey. That’s the triangle of truth.” Piltch observes that “Buddy knows exactly what’s going to happen when Trigger gets there. He was constantly aware of what Trigger’s space would be. It’s pretty impressive to see that.”

Cannon counters, “I kind of expect where Willie will play, and then he always plays somewhere else! But it works.” Nelson jokes that “Trigger would like to be out there all the time. He can get a little hoggy now and then. You have to pull him back or he’ll go crazy.” In fact, Trigger’s on his best behavior, with one spotlight moment, a dazzling solo on the album’s buoyant opener, “Fly Me to the Moon.”

Back in 1994, Nelson numbered among the guests for Sinatra’s Duets II, joining him on the Gershwins’ “A Foggy Day” and on “My Way” (the latter not released until 2005). Cannon and Rollings considered creating a from-the-grave duet, possibly revisiting one of those cuts. But, says Rollings, “Frank was old and tired when he did those tracks, so it wasn’t going to work.” Instead, they invited Norah Jones to join Nelson on “What Is This Thing Called Love.” Seven years prior, when Wynton Marsalis and Nelson celebrated Ray Charles with the live Here We Go Again, Jones had paired with Nelson on four tracks. “We’ve been great friends for years and years,” he says, “and she’s one of my favorite singers.” Rollings says her appearance “serves the record first and foremost, with the added benefit that she’s hip.”


Although My Way’s material is distinctly Sinatra’s, the interpretations are pure Nelson. “The minute he started singing them, they became Willie Nelson songs,” Rollings says. “I’ve worked with Lyle Lovett for years and Lyle is similar in that they can’t be anyone but themselves. They so fully occupy their artistry that there’s nowhere else for them to go. The authenticity of that is extremely powerful, and in Willie’s case is magic.”

Preview, buy or download My Way on Amazon!

Originally Published