Willie Nelson’s Second Love Letter To Sinatra

Read Our Review Of ‘That’s Life,’ The Country Legend’s 71st Studio Album

On March 8th 2021 » By Andrew Winistorfer

willie nelson that's life header

Every week we tell you about an album we think you need to spend time with. This week’s album is That’s Life, a new album of Frank Sinatra covers from country legend Willie Nelson.

When Willie Nelson was 10, he discovered his favorite singer ever, the person who has remained in that throne for the Red Headed Stranger over these last 75-plus years: Frank Sinatra. “There was a tenderness to his voice, a purity and an ease of phrasing,” Willie writes in It’s a Long Story. “When he sang the popular songs of the day, I marveled at the natural way he told a story.” Those same words could so easily be said about Nelson, who, since he did an album of standards on Stardust, still his most popular selling album ever, has been one of the best interpreters of the American songbook we have, a man simultaneously keeping us in touch with songs that are 100-plus years old while continuing to add to that canon.

It took until 2018 for Willie to give Frank the full album treatment, when he released My Way, an album that filtered Sinatra selections through Willie’s light organ and acoustic guitar-heavy honky tonk, a Willie album that just so happened to be all songs that were made famous by Old Blue Eyes. Last year, while holed up due to COVID, Willie decided to go back to the Sinatra songbook for his 71st studio album, That’s Life, an 11-song album that delivers these songs warmly and faithfully, an album equivalent of the giant hug we’ve all been missing from our loved ones during quarantine. But where My Way felt like Frank entering Willie’s world, thanks to recording at Capitol Studios backed by string arrangements and ’40s atmospherics, That’s Life feels like Willie entering Frank’s world, donning a black suit with a tie undone, drinking a highball while telling the stories of these songs. It’s an album that’s impossible to not widely smile throughout.

The title track is the centerpiece of the album, a downtrodden song that mirrors so many of Willie’s greatest hits (what’s “The Last Thing I Needed, First Thing This Morning” than an update of “That’s Life?”). Twinkling pianos drive the song forward while Nelson’s weathered bird call of a voice delivers on all the pathos of the song. Same goes for the slightly more jauty “Lonesome Road,” and the Las Vegas jackpot sounding “Luck Be A Lady.” “Nice Work If You Can Get It” crackles with a romantic flourish and “I Won’t Dance,” a duet with Diana Krall, is light and playful. Willie sounds like he’s having a complete blast spending this time in Sinatra’s oeuvre, showing that that even after 65 years in the music business, it’s possible to find inspiration, the willingness to have fun, and new ways of cracking open old chestnuts. Willie Nelson is a national treasure, and That’s Life is a delight. Protect him at all costs.

Andrew Winistorfer

Andrew Winistorfer

Andrew Winistorfer is Vinyl Me, Please’s Classics and Country Director, and an editor of their books, 100 Albums You Need In Your Collection and The Best Record Stores In The United States. He’s written Listening Notes for more than 20 VMP releases, and co-produced Nat Turner Rebellion's Laugh to Keep From Crying. He lives in Saint Paul, Minnesota.

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