02/08/2013 10:29 am ET Updated Apr 10, 2013

Callaway Channels Streisand at LA's Disney Hall

It's an unwritten rule in the cabaret, jazz and Broadway worlds: If you're performing a solo show, think twice about singing classic songs associated with Barbra Streisand. Approach Liza with caution, and beware of Judy. Nobody expects you to surpass the originals, and you could embarrass yourself trying.

But some performers can't seem to help themselves -- driven to leave their mark on songs that would seem to defy re-interpretation. So it is with Ann Hampton Callaway, a veteran chanteuse and jazz belter from New York who will be performing "The Streisand Songbook" this Sunday at Walt Disney Concert Hall.

Despite numerous awards under her belt, a Tony nomination, TV songwriting credits (the theme from The Nanny), a longtime love affair with the Great American Songbook and 12 well-received albums, Callaway might raise eyebrows with this weekend's song list: Backed by a trio, she'll be performing hallmark tunes like "Don't Rain On My Parade," "People," "Evergreen" and other mega-hits indelibly linked to La Streisand. Why take such a leap?

"At my stage in the game I have dared myself to take risks with songs that I love, but previously stayed away from because I was so well-behaved," said Callaway, several days before flying out to Los Angeles. "I feel more fearless now and I don't feel bound by the worry that, 'Oh my God, this is Judy Garland's song or this is Barbra's song. I feel like I've earned the right to do these songs, and the challenge is to find my own personal resonance in them."

Callaway certainly has the vocal chops to tackle such timeless material. Although she began her New York singing career in 1979 as a quietly introspective cabaret performer, she has emerged as one of America's most accomplished and versatile jazz singers. Her material blends old and new, running the gamut from George Gershwin and Cole Porter to Joni Mitchell and Paul Simon, and her sonorous voice can swallow a room with rich, lower registers and scat-singing soprano riffs.

But the biggest key to Callaway's success may be that she has enjoyed a warm and productive professional relationship with Streisand for many years. The legendary singer has recorded two songs written by Callaway -- "At the Same Time," an anthem celebrating peace and understanding, and "I've Dreamed of You," a poignant tune that became Streisand's wedding song to James Brolin. The two singers were put in touch more than a decade ago by mutual acquaintances like vocalist Amanda McBroom and Jay Landers, Streisand's A&R executive, at a time when Streisand was scoping out new material for several projects.

Callaway has continued to write new material for Streisand, and the collaboration gave her a wealth of insights to draw on as she began assembling her tribute show. Over the years she's observed Streisand at work in the studio, swapped ideas for songs, helped write patter for her live shows and had lengthy conversations with the singer on everything from the psychology of vocal performance to mutual New Year's resolutions.

"It's been a tremendous thrill to meet her in person, and I've had wonderful encounters with her," said Callaway. "So I'm not just putting this show together out of thin air. All of that background has helped me create a performance that now truly reflects my own personal experience."

When she wrote "I've Dream of You," for example, Callaway tried to craft a song that captured Streisand's feelings for Brolin: "I did a lot of research about their relationship and then, my God, she sang it at her wedding reception. I finished it three days before she got married, and I got to hear her do it live. She had clearly met the love of her life. These are the kind of emotions I hope audiences will connect with."

The singer will have impressive company during her Los Angeles gig: She'll be joined by lyricist Alan Bergman, who along with his wife, Marilyn, has penned some of Streisand's most memorable songs, including "The Way We Were," "How Do You Keep the Music Playing," "You Don't Bring Me Flowers," "The Way He Makes Me Feel," and others.

"The Streisand Show" recently won top honors in the New York awards for Best Cabaret Show, and Callaway is looking forward to recording the performance. But putting her own stamp on material so deeply familiar remains a challenge; it's a battle she faces every time she steps in front of a live audience.

So how has Callaway done it, song by song?

"Don't Rain on My Parade": "I told my arranger I wanted the song to be just like the Broadway score (from "Funny Girl"). That's a well-known theatrical song and when you hear it you just want to go back into the place of that show. I didn't do my own take on the song."

"Evergreen": "One night I came up with a swing version of the song. I had to wonder -- will it offend people if I do a whole different version of this song? But I just love the arrangement."

"People": "I had to work really hard to get what I wanted for this song. I had to go deeper than I knew how to do before, in terms of acting the song, and finding an emotional resonance that for me was profound but also very risky."

When Callaway performed the Streisand tribute at 54 Below in New York, Stephen Holden, writing in the New York Times, noted that she doesn't sound anything like Streisand, but said the two share a fundamental, unshakable romanticism." He added that, regardless of the material's sentimentality, "voices that can really put it over are all too rare." A review by the Concerts and Cabaret website praised Callaway's powerful voice and presence "in what might be a daunting or daring or disastrous task for lesser singers."

If nothing else, the Streisand Show is Callaway's way of saying thank you. Born in Chicago, she and her sister, Liz (who is also an accomplished singer and recording artist) grew up adoring Streisand. She listened endlessly to the phenom's early LP's, carefully studying every vocal nuance and dramatic moment. Years later, when it came time to imagine the ultimate tribute show, she hesitated -- but only for a second.

"At first I thought, 'Barbra's a legend. Why do this?' Then I realized that I had done the same kind of show for Ella Fitzgerald, but only after she was gone. And I thought -- I want to do this for Barbra now. I want to let her know while she's alive what she meant to me."

Ann Hampton Callaway will present The Streisand Songbook at Disney Hall on Sunday, February 10 at 7:30 p.m.