Rickie Lee Jones takes on the Great American Songbook

How can someone dare to stack their new versions alongside established classics by the likes of, say, Frank Sinatra, Billie Holiday, Tony Bennett, Ella Fitzgerald or Nat King Cole?

 Perhaps they can’t. But as long as they can find their own way into a song and make a lyric sound lived-in and its message true, that should be enough. Maybe even more than enough.

Rickie Lee Jones, whose latest album, “Pieces of Treasure,” takes up that very challenge, has some thoughts.

“The first thing is, if you have an emotional connection to the song, you’ll probably interpret it in such a way that somebody is going to go, ‘That’s how I feel about it,” Jones says via Zoom from her home in New Orleans.

The classic songs she chose to record for the album — “Just in Time,” “One for My Baby (and One More for the Road)," “All the Way” and “September Song,” among others —  have been done so many times, “they’d almost been run over,” Jones says. “So I had to give them life and dimension again.”

Her technique, she continues, is “to put on the skin of a song or find a character who’s singing it. I kind of act the songs. And in being an actor, I know everything there is about the song. I know where we’re sitting and who’s at the bar and what’s on the jukebox.”

In a way, that is how Jones has always approached her art, even when singing her own compositions. “When I did ‘Chuck E.’s in Love’ — the 1979 hit song from her debut album — I brought all those characters to life. People thought I was that girl. And I was partially that girl. But more, I was a songwriter creating a thing.”

Jones may be able to slip in an out of character when she sings, but she had to drop any kind of façade when she wrote her recent memoir, “Last Chance Texaco,” which was published in 2021. The book deals with her peripatetic and often painful childhood, her parents’ volatile relationship, her time as a teenage runaway and later, a heroin addict, as well as her adventures with such characters as Tom Waits, Lowell George and Dr. John. Through it all, music was always there as a balm, a healing force.

“I knew it was a great story,” she says.

She always wanted to tell the story of her family, she adds; “All those people who had such hard lives. There’s a line in the book that says, ‘Those early pioneers, dust now, just a trickle down your back. But their lives were so full, and they fought so hard not so long ago and then they died.’ So the very least I can do is to say their names out loud.”

Her career has had its peaks and valleys. She was a hit right out of the gate with “Chuck E.’s in Love” and a platinum album that landed her on “Saturday Night Live,” on the cover of Rolling Stone — twice — and won her a Best New Artist Grammy. Her second album, “Pirates,” was a critical and commercial success, and many regard it as her masterpiece.

Jones continued releasing albums — 17 of them now — shifting seamlessly between pop and jazz, and even experimenting with electronic textures on 1997’s “Ghostyhead.” She recorded several covers albums, taking on rock and soul classics and, yes, some standards as well. She won another Grammy in 1990, duetting with Dr. John on “Makin’ Whoopee.”

On the one hand, after those early years of success, you could say that the music business didn’t really understand or support her in the manner her music deserved. On the other, you could say that she followed her muse and always stayed true to herself.

“When I’m dead I think is when those look like great decisions,” Jones says with a laugh. “When it’s happening, people are going, ‘Wow, that was a mistake.’ But I think it’s the right way.”

What Rickie Lee Jones Pieces of Treasure Jazz Quintet • When 8 p.m. May 20 • Where City Winery, City Foundry 3730 Foundry Way • How much $65-$85 • More info 646-751-6033; citywinery.com/stlouis