Skip to content Skip to footer

‘An Old Sweet Song’: Pittsburgh CLO’s Lady Day Gets Into the Billie Holiday Spirit


For Gabrielle Lee, who has sung on stages all over the world, starring in Lady Day at Emerson’s Bar & Grill will be a gateway back to her future.

The future is tomorrow, May 17, 2024, when she will help Pittsburgh CLO open its 77th summer season by portraying jazz-blues legend Billie Holiday.

“I grew up listening to Billie, and I first sang “God Bless the Child” at an eighth-grade singing competition. My granny made a little flower for my head, and I had on a gown,” recalled Lee.

Sporting Holiday’s signature look, young Gabrielle made a comeback from 10th to finish second in that competition, and “God Bless the Child” became a signature song she shares with Holiday. 

Gabrielle Lee portrays Billie Holiday in Pittsburgh CLO’s season-opening production of Lady Day at Emerson’s Bar & Grill.

Lee is making her PCLO debut and just getting to know the city, but she goes back to the late 1990s with her director, Tomé Cousin. Back then, they worked together on a musical adaptation of the baseball movie The Bingo Long Traveling All-Stars & Motor Kings, and the pair have stayed in touch over the years. 

They have in common their knowledge and appreciation of Holiday being spurred by Diana Ross’ Oscar-nominated portrayal in the 1972 film, Lady Sings the Blues. The fascination with and influence of Holiday, who died in 1959, at age 44, continues unabated – Lady Day, with a script by Lanie Robertson, earned Audra McDonald her sixth Tony Award, as best actress in a play, in 2014. 

The character of Holiday in the play is in conversation with her audience, not long before her death, while performing in a seedy South Philadelphia bar. More than a dozen musical numbers are interlaced with unflinching and often humorous reminiscences about a life marred by racism and substance abuse. Or as Lee put it, “We find laughter even in the hardest times. We make rainbows out of our tragedies, I think.”

In the play, Holiday speaks fondly of her mother, who was know as “The Duchess.”

“She was very close to her mom, and I’m close to mine,” said Lee. “I lost my mom, but she’s still with me – I talk as if she’s still here. … I dedicate this to her. The last show ends on her birthday, June 30th, and I was like, ‘OK, Ma, this is for you.’ ”

Lee bantered cabaret-style as we speak on a conference call with director Cousins, which makes the Greer Cabaret Theater an apt spot for this two-hander – she shares the stage with music director Kenney Green-Tilford, as Holiday’s accompanist and confidant, Jimmy Powers.

“I think God gave me the gift of the gab. The intimate setting, for me, that’s where I live,” she said.

Asked about which of Holiday’s songs Lee enjoys singing most, she said, “All of them,” but offered a tidbit of “Ain’t Nobody’s Business,” and the lyric “an old sweet song” from “Georgia on My Mind,” and recounted her early experience with “God Bless the Child,” which was co-written by Holiday with Arthur Herzog Jr.

Kenney Green-Tilford

Cousin said, and Lee echoed, that they were “blessed” to be working with Green-Tilford on finding the spirit of Billie Holiday, who on Facebook said, “Excited about [Cousin’s] vision and take on this piece. It’s gonna be a gas!”

Many musical scholars have tried to define Holiday’s distinctive vocal acuity, which has been summarized as “strongly inspired by jazz instrumentalists, [she] pioneered a new way of manipulating phrasing and tempo.” Her delivery and improvisational skills kept audiences rapt.

The aim of Lee and Cousin is not to imitate but to channel what made Holiday so special, and let Lee’s talents soar.

“As an actor, you don’t really want to mimic anyone because you cheat yourself of the experience of having to embody someone who is like an icon,” Lee said. “You want to experience what they were feeling and how they sounded, and allow that spirit and that vibe to just incorporate into you. That’s the journey that makes an actor.”

Cousin thought of Lee for the role because, “first of all, you have to have a person with a beautiful voice,” he said. “And then it’s the combination of the actor and the voice that’s really crucial to this material, because it’s basically a solo. They’re out there carrying this whole thing, so it was important to have had that experience.”

The director noted that, while Tony-winner McDonald was “absolutely wonderful” in Lady Day, an actor intent on imitation would be like “impersonating Audra impersonating another person.” 

“None of us really knew [Billie Holiday] in reality, he continued, “so we have created an ideal of who we think she is and what she sounded like, and some little trademarks.”

The rest is all Lee, who has forged her own path, with off-Broadway and regional productions including Chicken & Biscuits, Once On This Island, Dreamgirls, Smokey Joe’s Café, Showboat and Little Shop of Horrors. She also has appeared in concert with the New York Pops, as well as the Cab Calloway and Ray Charles Orchestras, and has done backing vocals for Steely Dan and Harry Belafonte, among others.

Ayana Del Valle

For the demanding role, Lee will be onstage May 17-31, then, from June 1 – June 30, Ayana Del Valle will perform as Lady Day on Wednesday evenings and Saturday matinees, while Lee will continue to perform all other performances. Del Valle previously played the role at the Cider Mill Stage in Endicott, N.Y.

Cousin noted that there is a responsibility to the real-life Billie Holiday and the character of Holiday, but also to the actor, who among her tasks is “to transform the audience to the time period,” he said. “And that’s a bit of a challenge because [the Greer] is such a beautiful club,” which the Emerson’s of the title was not.

The director choreographer said to expect the audience experience to be transformative, not just from the stage, but the venue itself, “so it’s not just kind of sitting back and just enjoying these wonderful sounds and stories,” but an overall experience.

Without giving too much away, Cousin said, “I really enjoy watching audiences be emotionally moved and physically move. So there’s moments where the focus is here, the focus is there in the space … her energy is very active.”

Lee’s energy comes crackling through the phone when she talks about her first appearance with Pittsburgh CLO. She came close once before, she said, with a callback for Adelaide in Guys and Dolls

“Oh, I’ve always wanted to work with Pittsburgh for years!,” she said. “Good things do come to those who wait, if you can hang in there long enough.”


Lady Day at Emerson’s Bar & Grill is at the Greer Cabaret Theater, Theater Square, Downtown, May 17 – June 30, 2024. Tickets: For “Removing Barriers” access, visit