Willie Nelson Extends Homage to Frank Sinatra with ‘That’s Life’

Willie Nelson’s latest reveals the venerable troubadour as a stoned Sinatra, laid back and groovy, a ripped philosopher pontificating on the mysteries of life. It’s a world-class performance, not bound by any cabaret conventions or corralled by any industry cowboys seeking to rein him in. That’s Life is unmistakably Willie trying on Sinatra’s suit, but it’s the same old scruffy Willie underneath, comfortably broken in and well-aged.

It’s not Nelson’s first rodeo with Sinatra. The two have ties going back to 1978, when Nelson cut Stardust, an album of pop standards including several Sinatra had taken a swing at. It became his best-selling album to date. In 2018, Nelson’s all-Sinatra collection My Way won him a Grammy. In an interview that year for AARP, Nelson acknowledged that he learned a lot about phrasing from listening to Sinatra. Sinatra is said to have become a fan of Nelson after hearing Stardust, agreeing to open for him for a string of shows in Vegas in 1984. Even though the collab was short-lived, with only one show done before Sinatra bowed out due to throat problems, the two remained friends and mutual admirers.

The songs on That’s Life are more like tributes than makeovers. There’s plenty of snappy big band arrangements, with Nelson sounding a bit peppier than usual on Sinatra classics like “Luck Be a Lady.”

They couldn’t dress him up in real life, but an animated version of Nelson was squeezed into a tux, untucked twin ponytails flying around for his duet with jazz chanteuse Diana Krall for “I Won’t Dance.” The animated Willie kicks up his heels on the video, dashing around in a very un-Willie like manner pursuing Krall through space as he bops along smoothly over the brassy, string-sweetened arrangement.

The title cut that Sinatra made his signature tune comes across here as pure Willie. It’s so damn cool and laid back, sounding like Nelson’s kicked back in a hammock, looking back at his life through a mellow, smoky haze, Mickey Raphael’s harp and Paul Franklin’s steel guitar making tracks that transport it from a cabaret to a honky-tonk.

Nelson goes a little further south than Sinatra did on “I’ve Got You Under My Skin,” giving it a samba framework and deconstructing it country-style with what is almost a recitation, a talk/sing performance mellowed out with a few soothing tonsil strokes.

The honky-tonk cabaret turns its lights down low as Raphael makes a melancholy chromatic harp visit on “In the Wee small Hours of the Morning” to accompany one of Nelson’s most moving presentations here on a song so Sinatra-ized it would seem impossible for another performer to get under its skin and walk about. But the makeover here is so good you’d swear it was a Willie lullaby he’d croon to himself on the bus to self-medicate road fever symptoms.

In the same AARP interview mentioned earlier, Nelson was asked about his secret for life. “Do what you want to do,” he said. “If I don’t want to do it, forget it. But if I do want to do it, get out of my goddamn way.” Now that’s life, Willie-style.