A Classic Sings A Classic: Watch Willie Nelson’s Lyric Video For “That’s Life”

Frank Sinatra released 59 studio albums before he passed away at 82. His old pal Willie Nelson has eclipsed both numbers; at age 87, his studio album tally is about to hit 71 (not counting collaborations) with the Feb. 26 release of That’s Life, his second collection of Sinatra songs. The first, My Way, released in 2018, earned him his ninth of 10 Grammys.

Legacy Recordings is giving listeners a taste of what’s to come with today’s release of the title track as the first single. Also premiering is a lyric video for the song, in which famed illustrator Paul Mann, a beacon of the alternative movie poster movement, paints Nelson and his beloved guitar, Trigger, in a Sinatra-like album cover pose.

After Sinatra released his version of the Dean Kay-Kelly Gordon composition in 1966, it became one of his signature songs. Nelson puts his own jazzy spin on the Great American Songbook classic with prominent accompaniment from coproducer and arranger Matt Rollings on piano and longtime Family Band member Mickey Raphael on harmonica.

“Sinatra was Willie’s favorite singer and they were friends,” says Rollings, who began recording classics with Nelson and longtime producer Buddy Cannon on Summertime, a collection of Gershwin songs Nelson released after winning the Library of Congress’ Gershwin Prize for Popular Song in 2015.

In American Songwriter’s 2018 legends issue cover story, Nelson said of that album, “I really ripped off Sinatra. I went to the internet and found out everything on there that Sinatra had done for Gershwin and I said, ‘Well, I’d like to do it exactly that way.’ So I sent all that to my producer and I said, ‘Good Luck.’”

That album won him the Grammy for Best Traditional Pop Vocal Album. Two years later, he won that same award for My Way.

Ironically, Nelson’s label wasn’t too keen on the idea when their finally successful outlaw country singer decided to release an album of pop standards in 1978. But he was on a roll; since hitting No. 1 on Billboard’s country chart with Red Headed Stranger in 1975, three of his next four releases also reached No. 1—the outlier, To Lefty from Willie, made it to No. 2.

Stardust not only zoomed to No. 1, it stayed on the chart for a record 10 years. By then, Willie Nelson could record whatever he wanted — his way.

Here’s the lyric video for Willie Nelson’s version of “That’s Life.”