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Willie Nelson’s latest album, That’s Life, brings a new flair to some of Frank Sinatra’s greatest hits. Largely staying true to the original Sinatra source material, old-time fans of these favorite tracks will find Nelson’s take an easy switch. However, Sinatra’s hits, filled with his boyish charm and flirtatious crooning, benefit greatly from Nelson’s coarse, aged vocals and image. 

It’s a welcome change of pace to hear Nelson sing along to a big band –– twinkling piano, slow saxophone solos and all. It’s a marked stylistic shift from Nelson’s reputation as a country and folk singer. Yet, at 87 years old and with a discography of over 144 albums under his belt, Nelson has earned the right to mix things up a bit.

Sinatra’s songs, full of playful bemoaning of life’s cruelties, feel more authentic when paired with Nelson’s extensive stock of personal experience. That’s Life pokes fun at the ups and downs of life and luck. Sinatra’s ending remark “If there’s nothing shaking come this here July / I’m gonna roll myself up / In a big ball and die” makes the songs easily relatable. It’s Nelson’s country history and his role in the outlaw country genre of the 70s that transforms the song into something far more tangible. 

Outlaw country was music for and about the “underbelly” of society — prisoners, criminals and flawed men fighting to live in a broken system. The genre gave voice to dark realities that lay beneath the blue-collar American dream. Nelson’s version of That’s Life retains Sinatra’s humor, yet balances fun with the sobering acknowledgment that it’s not always easy to pick yourself up when life knocks you down. There is an added layer of credibility when it’s coming from Willie Nelson –– tough as nails, old as dirt and an “everyman’s man.”

“In the Wee Small Hours of the Morning” similarly anchors itself to Nelson’s cultural role and age. Whereas Sinatra’s version was heartbreakingly romantic and somber, the faint gravel of Nelson’s voice and country-twang of “mornin’” adds a new sense of deep longing to the song, as if Nelson has been waiting a lifetime, his lifetime. 

Some tracks lose the bombastic quality of Sinatra’s dynamic range and crooning style — Nelson’s own songs are characterized by soft-spoken storytelling and introspective, bare-bones studio recordings. Noticeably, the big band instrumentation of That’s Life has been toned down to accommodate Nelson’s singing style. Songs like “You Make Me Feel So Young” feel restrained: Nelson falters in the song’s traditional crescendos. Where Sinatra would let loose, Nelson gently steps back. However, the bright, energetic brass section and steady tempo add enough color to keep the album from becoming washed out. 

Sinatra-style jazz isn’t a natural transition for Nelson, both stylistically and due to the limitations of his older voice. Yet, rather than fizzle out, Nelson manages to imbue a pleasant intimacy into his cover album — That’s Life is buoyed by the fact that Nelson really knows life. 

Take a listen to Willie Nelson’s That’s Life this week — between these two music legends, it’s impossible to go wrong. 

Daily Arts Writer Madeleine Virgina Gannon can be reached at