In the ’80s, Frank Sinatra and Willie Nelson appeared side by side in a televised spot for NASA’s Space Foundation, the former wearing a tuxedo and the latter in braids and denim. “Willie, it’s obvious that we don’t share the same tailor,” Sinatra said, before pointing to Nelson’s headband. “I mean, what do you call that thing there?”
“I call it ‘my way,’ Francis,” Nelson replied with a grin.
The subtext was that if these two could agree on the value of space-age technology—"It’s led to a lot of things that have helped all of us, city dudes and country cousins alike," Nelson said—then more commonalities surely must exist. On My Way, Nelson extends that thought with a set of soulful, affectionately rendered covers pulled mostly from Sinatra’s defining ’50s–’60s run. The approach is both jazzy and twangy, playful and reflective, with Norah Jones joining in for a lively duet on “What Is This Thing Called Love.” And though Nelson’s voice is still strong at 85, his renditions of the elegiac “It Was a Very Good Year” and the title cut in particular feel almost too poignant. For Nelson, it was Sinatra’s talent for phrasing that he related to most. “He didn’t worry about [being] behind the beat or in front of the beat, or whatever—he could sing it either way,” Nelson told AARP The Magazine in early 2018. “And that’s the feel you have to have.”