The renowned jazz and cabaret singer Michael Feinstein has long been dedicated to mining the seemingly endless recesses of the Great American Songbook, with an emphasis — as anyone familiar with his unique backstory is aware — on the Gershwin catalog.

Before his career took off, so the story goes, Feinstein was just 20 years old and new to Los Angeles when he began a six-year stint as Ira Gershwin’s archivist, working closely with the master lyricist to catalog, among other things, the music he wrote with his brother George in the 1920s and ’30s.

Feinstein put that experience to use on his first record, “Pure Gershwin,” and followed up with two more similarly dutiful Gershwin tribute albums in the late ’90s. His latest album, released this month, represents something of a return to form as well as a stylistic departure for the seasoned Gershwin interpreter.

On “Gershwin Country,” Feinstein, now 65, puts the Gershwin songbook through a country prism. The album, recorded with a session band in Nashville, includes cameos from such heavy hitters as Dolly Parton, Brad Paisley, Roseanne Cash and Liza Minnelli, who served as executive producer and was Ira’s goddaughter.

While the setting may have been somewhat unfamiliar for Feinstein, “the idea of singing with artists who still are focused primarily on interpreting lyrics, which is what country music is still about,” was appealing to him, he said in a recent interview with Jewish Insider. “It may be the last place where that is so.”

Not that he hasn’t gotten some quizzical stares from those who are surprised by his latest turn. 

“When I mention it now to anybody who is unfamiliar with the concept, they always give me a funny look or their voice is raised in a certain inflection as if, ‘Really? You really mean this?’ because it sounds like an odd concept,” he said. “But it made sense to me musically because great songs survive because of the ability to reinterpret them or adapt them to a different style, and they don’t lose the essence of what they were created to express.”

The interview has been edited and condensed for clarity.

Jewish Insider: In the liner notes to “Gershwin Country,” you write that Maya Angelou, who was one of your “close friends,” originally “opened” your “eyes to the breadth and scope of Country music,” and that you were “changed for it.” Can you tell me the backstory there?

Michael Feinstein: We were friends for a number of years. We met through the writer Shayna Alexander, whose father was a songwriter, and my connection with Maya was always through songs, songwriters and music. Through the years, she would share stories about songs that she loved or ask me if I knew this song or that song. 

Also, she had toured in the company “Porgy and Bess” in the 1950s, including when that company went to Israel. Amazingly, I found a scrapbook of “Porgy and Bess” in Israel that somebody had collated and carefully pasted in with all these articles, including a feature article about Maya from that period, which I gave to her and she, presumably, deposited into her archives. I’m sure it’s there somewhere. We had this bond over music that was very special to me, and we actually wrote one song together for Lincoln’s 200 birthday, which I performed on the steps of the Lincoln Memorial. 

But anyway, I was staying with Maya in Winston-Salem [N.C.], her home, and, as usual, she was playing some country music. She started talking about why country music was important to her and what she thought it represented for our country. Anything that came out of her mouth was, of course, extraordinarily compelling because she was so smart and had such an incredible perspective about things and always came from a place of unconditional love. So, much to my surprise, I found myself saying, “Well, I’d love to do an album of country songs,” and “would you consider executive producing it?” She said, “Yes, I will allow you to use me in that way. It would be my joy.” Then she became ill and passed away and it never happened. So that, in a nutshell, is that story.

JI: So how did the album come about, years later?

Feinstein: I was lying in bed in an early morning reverie, trying to avoid getting up, and a lot of times thoughts drift through the brain that are sometimes interesting and more often not. I started thinking about Maya and about country music, and suddenly the idea of Gershwin in a country vernacular came to me, and it didn’t seem crazy. When I mention it now to anybody who is unfamiliar with the concept, they always give me a funny look or their voice is raised in a certain inflection as if, “Really? You really mean this?” because it sounds like an odd concept. But it made sense to me musically because great songs survive because of the ability to reinterpret them or adapt them to a different style, and they don’t lose the essence of what they were created to express.

The idea of performing Gershwin with Nashville musicians was very seductive to me because I performed with the Nashville Symphony a number of times and discovered that there are fine, well-educated Nashville players who also do sessions and can improvise and have the unfettered ability to work creatively without limitation. That was one of the things that made it seductive for me, [as was] the idea of singing with artists who still are focused primarily on interpreting lyrics, which is what country music is still about. It may be the last place where that is so, the last genre.

JI: How did you make song and artist choices?

Feinstein: The process of choosing songs was endless because I know the Gershwin catalog so well. I started making lists of lesser-known, obscure material, and then when I started working with the producer, he and I started whittling it down and we started figuring out the songs that we felt would best lend themselves to this treatment. When it came to choosing performers, the first person I asked was Dolly Parton, whom I had met years before at the home of Roddy McDowall, and she generously said yes. Then I asked Brad Paisley, with whom I was having lunch through mutual friends, and he said yes immediately. 

JI: So those two helped clear the way for more people to sign on?

Feinstein: Yes. It was like a jigsaw puzzle where you don’t know if you have all the pieces in assembling it, because it’s a very complex process of choosing keys and figuring out routines that are complementary and all of that, and it took a great deal of time. I didn’t mind that because this was something that I wasn’t trying to do quickly, but I was trying to do right.

JI: How did you feel everything came together?

Feinstein: I’m very pleased because I feel like it is true to the spirit of the Gershwin songs. It feels like a Nashville-based recording, and the singers with whom I’m paired, I think they’re all really remarkably gifted and sing these songs extremely well. It was a joy.

JI: What do you hope people will take away from this album?

Feinstein: My hope is that people will simply enjoy the songs and performances on their own terms. In other words, one does not have to know Gershwin or know the history. Hopefully, they’ll just hear it and like it. That’s the idea, that this is potentially a crossover project in that it could be as appealing to those who like traditional country music and will appeal to those who like Gershwin and those who like American popular song. It’s a musical assimilation in that, ultimately, I want the work to speak for itself. One needn’t know anything about Gershwin or anything about the history. I’m just hoping that the songs themselves and the performances will have fundamental appeal.

JI: Have you ever performed in a country context before?

Feinstein: Well, impromptu, like, in a nightclub in Nashville, I’ve gotten up with a band that had steel guitar and sung, but I haven’t done an actual concert of that. When I performed with the Nashville Symphony, it was a program of American popular song. It struck me when I was putting this project together that Willie Nelson did a Gershwin album, but he went the other way. He didn’t work with a Nashville band. He did a more traditional album. So I think this is probably the first recording of Gershwin that has an authentic Nashville group assembled for it.

JI: Did you find that your collaborators were familiar with the Gershwin songbook?

Feinstein: Some yes and some no. Dolly certainly knew Gershwin, but I don’t know that she really was that familiar with “Love Is Here to Stay.” They approached the songs as songs. When I asked Rosanne Cash, she of course knew Gershwin. I had met her at a party, and we ended up singing an impromptu duet of the Irving Berlin song “You’re Just In Love” from “Call Me Madam,” and that memory stuck in my brain, and I stayed somewhat friendly with her. When I asked her to do it, she said, “This is totally out of my wheelhouse, but that’s what excites me about it.” That’s what was fun for them, I think, and they sang in their style and I sang in mine.

One thing that was really important, though, was singing the duet in the same key, because often you’ll hear duet recordings that, I think, are slapped together for the sake of trying to combine two artists to sell recordings, and one artist will sing eight bars in one key and then modulate to the female key and then modulate back to the male key. It’s just like, you sing eight bars, I sing eight bars, and this is the polar opposite of that — every division of line and lyric was created for the purpose of the text.

JI: “Clap Yo’ Hands” was an interesting and somewhat more obscure choice. How did that find its way onto the album?

Feinstein: It’s one of the few Gershwin songs that has kind of a gospel or spiritual feel to it. There’s a contemporary recording from the time the song was written, in 1926, for a show called “Oh, Kay!” that starred Gertrude Lawrence, and a recording was made by a great songwriter and singer named Willard Robison. He did it very much in a gospel style because Willard was from Shelbina, Missouri. He wrote a lot of religious-tinged songs and songs about revivals and such, and it was from that Willard Robison recording that the idea came to do it that way.

JI: What do you think listeners can take from Gershwin songs now?

Feinstein: I think that the timeless nature of Gershwin songs is comparable to the other great songs of that time in that they’re such eloquent expressions of oft-expressed emotions. These songwriters were always trying to find fresh ways to express romance and to express love without saying “I love you.” One of the reasons that Bing Crosby loved working with the lyricist Johnny Burke is that Crosby hated to sing “I love you,” and so Johnny Burke would write all these songs that referenced love but weren’t obvious. And that’s what Ira Gershwin tried to do with “Someone to Watch Over Me,” which is a song that he wrote when he married his wife, Leonore, in 1926. And “Can’t Take That Away From Me” — what a brilliant way of expressing love for someone. You’re talking about the characteristics that open the heart. So these lyrical flights of fancy still appeal to the heart and to the mind because they’re charming, they’re heartfelt, they’re sincere, and even though some of them may have been written for commerce or written for the plot of a show, they have an authenticity about them that transcends time. 

JI: Did you ever talk with Ira about his connection with Judaism or his Jewish identity?

Feinstein: It’s funny. He was very dismissive about Jewish influences in his work, yet, he spoke Yiddish and he was culturally very Jewish. George spent a lot of time hanging out at the Yiddish theater. I mean, George Gershwin was a guy who spent as much time there as he did in Harlem listening to the Black stride pianists and going to Coney Island. So he soaked up all of the musical life of New York. Ira didn’t feel that George was particularly influenced any more by Yiddish musical theater than he was by anything else. But nevertheless, there are stories that were told by Sholom Secunda and others who were in contact with George when he was spending time with them, and Ira wasn’t privy to that. In Ira’s collaborations with George, they didn’t talk about Jewish music in particular. But it definitely was an influence. 

But during the High Holy Days, the family was not religious. They didn’t go to the synagogue and Mrs. Gershwin would pull down the curtains so the neighbors couldn’t see that they weren’t being observant. Yet Ira, in “Of Thee I Sing,” put in a joke that you’d have to be Jewish to get. There’s a scene where it’s the entrance of the French ambassador, and this chorus is singing a sort of pidgin French: “Garçon sir vous plait…” And then they sing “à vous tout dir vay à vous,” and it’s Yiddish for “where does it hurt you, where?” But Ira thought it sounded like French. He put in Yiddish as an inside joke. So that’s a great example of Jewish influence.

JI: Ira’s syntax also seems to have been influenced by the Jewish immigrant vernacular. I’m thinking, in particular, of the line “who would, would you?” from “The Man I Love.”

Feinstein: Yes, yes, well, his father had a very thick, Russian-Jewish accent. He was a very whimsical man who made a lot of jokes, and George would unashamedly introduce “Papa Gershwin” to the glitterati at his parties, you know, the toast of Broadway and Hollywood mixing with Morris Gershwin. So that says something about the fact that he was proud of his background and never hid anything, wasn’t observant, but proud of his heritage.

JI: Does that resonate with you as a Jewish performer?

Feinstein: I can’t say specifically. I mean. No, I don’t think of it in those terms. I mean, it’s just like when Jerome Kern was hired to write a musical about Marco Polo and somebody said, “How are you going to come up with all those Oriental songs?” And he said, “Don’t worry, it’ll be good Jewish music.”