Pamela Springsteen
When you think about the iconic voices of American music, Frank Sinatra and Willie Nelson must both be high on the list. And with his new album That’s Life, Nelson walks another mile in the Chairman of the Board’s wingtips.
Trading the honky-tonk for a cocktail lounge, and a denim tuxedo for a black tie, Nelson applies his own unmistakable vocals to Sinatra’s legendary songs. It’s a project that ends up feeling dressed-down and informal, but absolutely genuine—and like a heartfelt tribute to an old friend.
In truth, Nelson’s no red-headed stranger to the tunes made famous by Sinatra, who passed away in 1998. That’s Life marks the second time he’s covered the icon, and it’s the follow up to a 2018 project that turned out to be somewhat revelatory. That album was My Way, with Nelson covering standards like “Fly Me to the Moon” in his signature, syncopated twang, and That’s Life follows suit. Both projects highlight the similarities between a rough-around-the-edges cowboy singer and the hallmark of mid-century, masculine urbanity—and in fact, Nelson was a longtime fan. He told AARP magazine just before My Way that he owes much of his own enigmatic vocal presence to Sinatra himself.
“I learned a lot about phrasing listening to Frank,” Nelson said. “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.”
Indeed, Nelson has famously been a little “offbeat” his whole career. And after That’s Life arrived in February, he and Sinatra feel more like kindred spirits than ever. Produced by country kingmaker Buddy Cannon and Grammy winner Matt Rollings and recorded in the same hallowed studio where Sinatra worked for many years (Capitol Studios in Hollywood), it finds Nelson feeling comfortable yet engaged. He’s not doing a Sinatra impression—rather, imagining himself as a classic-pop singer, and doling out a cool and confident delivery with jazz-like unpredictability.
Over 11 songs, Nelson celebrates the swagger Sinatra brought to the post-war period, with Cannon and Rollings layering strings and horns to evoke the era’s refined, sophisticated aspirations. But it’s still Willie Nelson, so a light coating of Texas dust covers each song. The project opens with the plucky “Nice Work If You Can Get It,” with Nelson sounding as un-hurried as can be, if a little melancholy. Uptown becomes down-home for just a moment, as steel guitar and standup bass join a classic piano accompaniment. Later, a bouncy rendition of “I’ve Got You Under My Skin” leans heavily on Nelson’s charming warble, with little more than a piano and jazz-club drums to frame it. Nothing more is needed, and that’s mostly where the album stays.
The ageless “You Make Me Feel So Young” is one notable exception, as horns strike a bolder tone and Nelson playfully toys with the theme—plus a signature, uber-simple improvisation on his famous acoustic guitar, Trigger. Likewise, “I Won’t Dance” features the album’s only collaboration, with modern-jazz star Diana Krall giving Nelson a foil for his vocal gamesmanship, and a brassy, rhythmic rendition of “Luck Be a Lady” is the album’s most energetic moment.
But elsewhere, the title track speaks to the wisdom of Nelson’s years ... and perhaps the reason for his second Sinatra tribute. He’ll turn 88 next month, and with a hint of sarcastic humor, “That’s Life” finds him commiserating with the listener over a tough stretch of bad luck—a place we’ve all been to recently. But with a flash of the same optimistic charisma that made Sinatra an idol of American cool, Nelson reassures us that one day, the cards will come out in our favor again.
In the end, that hopeful ease is the main takeaway of That’s Life. It’s a gentle piece of easy listening, a cheerful reminder of better times and a way to appreciate the underplayed sophistication of Nelson’s voice. But it’s clearly also a loving tribute to a dearly departed friend. Nelson’s first Sinatra tribute earned him a Grammy for Best Traditional Pop Vocal Album in 2019, and the result here remains to be seen. But it’s surely something Ol’ Blue Eyes would raise a glass to.