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Review: Pittsburgh CLO’s Transcendent ‘Lady Day’ Delivers a Star Turn as Billie Holiday


In an alcohol-fueled haze of heartbreak and sardonic humor, when it was a struggle to stand on her own two feet, it was music that sustained Billie Holiday.

Lady Day at Emerson’s Bar & Grill, the musical play that opens Pittsburgh CLO’s 78th year, is about the dimming of a bright light in the worlds of music and social activism, while the production illuminates the talents of a performer new to Pittsburgh, in Gabrielle Lee‘s star turn as Billie “Lady Day” Holiday.

Gabrielle Lee as Billie “Lady Day” Holiday and Kenney Green-Tilford
as Jimmy Powers, in Pittsburgh CLO’s 2024 summer season opening show,
at the Greer Cabaret Theater. (Image: Matt Polk)

Lady Day is not your typical PCLO summer musical – the Tony Awards designate it as a play, written by Lanie Robertson, entwined with some of Holiday’s best-known and lesser-known songs. It is performed not in the usual summer home of PCLO, the 2,800-seat Benedum Center, but in the nearby 260-seat Greer Cabaret Theater. 

The intimacy of the venue suits the title, as Emerson’s has been described as a seedy hot spot in Philadelphia, a city that was not always kind to the jazz-blues legend. Owner “Em,” however, was, and willing to take a chance on Holiday in the late 1950s, when a lifetime of substance abuse was about to catch up to her. 

The God Bless the Child and Strange Fruit singer died in 1959, at age 44.

Lee embodies it all, seemingly ever more inebriated as she recounts the tragedies and triumphs of Holiday’s life, including time spent in a brothel as a teenager, until she had had enough and stumbled into a job as a singer. 

The band leader Benny Goodman came to see her, she recalls, and she later became the singer for Artie Shaw’s band – a joyful time onstage and often a racist nightmare off of it. Lee, at times matter-of-factly, with the shake of her head, talks of waiting in the bus until it was her time to sing, and delivers a scathing and somewhat humorous account of being denied the use of a restaurant bathroom, where she and her bandmates were already eating in the kitchen.

The static setting of a brick wall and dull windowed background, with a three-seat bar off to one side and a three-piece band on the other, grounds the Greer stage in the time and setting (if not for a cell phone that took a while to silence on opening night). 

Lee, swathed in an off-shoulder, sparkly white gown and silver heels, often staggers with a glass in her hand, daringly unsteady, while still oozing charisma and audaciousness as she recounts a life in which her mother and her music were her only touchstones of reliability.

That Holiday was unlucky in love – particularly with her “first and worst” husband, Jimmy “Sonny” Monroe, is well-documented. Still, according to Lady Day, she remained infatuated with Sonny. She speaks of him wistfully, and at times mistakes him for Jimmy Powers, played by music director Kenney Green-Tilford, at the piano. 

Green-Tilford portrays Powers as amiable but often exasperated, and with a drummer and bassist, provides a cleansing instrumental “Blues Break” while Lee’s Holiday collects herself offstage.

She reemerges, still reeling, but with a cuteness break in tow – her dog, Pepi (PCLO associate producer Billy Mason’s dog, Scrappy). 

Pepi (“Scrappy” Mason) joins Gabrielle Lee’s Billie Holiday onstage
in Lady Day at Emerson’s Bar & Grill. (Image: Matt Polk)

Throughout the performance, Lee never wavers in her honest portrayal, while singing in a voice recognizably Holiday’s – unexpected fluctuations in pitch, the distinctive phrasing and vibrato – while also revealing her own chops as a singer. 

She tells it as Holiday told it, sometimes to no avail, that she was not a blues singer, but somewhere between her inspirations, Louis “Pops” Armstrong and Bessie Smith. Declaring herself a jazz singer who also sang blues songs, she would add that she could not sing a song without having an emotional connection to it. 

The show starts as a concert might, with two consecutive songs, “I Wonder Where Our Love Has Gone” and “When a Man Loves a Woman,” then begins to spin into play territory, with Lee’s Lady Day at one point taking a turn through the audience. 

Lee’s comfort while addressing the audience is obvious, and her singing flows naturally as well, particularly on Holiday’s signature song, “God Bless The Child.” Swathed in mood lighting, notably on the eerie song about lynchings, “Strange Fruit,” Lee’s Holiday grows progressively drunker, stumbling physically and rambling through stories. At times with a wave of her hand, she drops bombshells about abuse she suffered as a child, the constant degradation forced on her as a Black woman, lest we forget we are in the 1950s, and the Civil Rights Act was not passed until 1964.

She jokes about her year in jail and West Virginia, which she calls “redundant,” and while also speaking of encounters with impolite white society, she talks of her great-grandparents – an enslaved woman and slave owner – which is how she got her birth name, Eleanor Fagan … it’s quite a lot, of music and biographical information, packed into 90 minutes with no intermission.

Gabrielle Lee stars in Lady Day at Emerson’s Bar & Grill for Pittsburgh CLO. (Image: Matt Polk)

There has been little let-up in the fascination with Billie Holiday’s life and music, and ways to reintroduce her to new generations. There are several enlightening documentaries, including the award-winning 2019 Billie. Movies such as Lady Sings the Blues and The United States vs. Billie Holiday have tread much of what is said here, and provided Diana Ross and Audra Day, respectively, with Oscar-nominated roles. Audra McDonald earned her sixth Tony Award in Lady Day at Emerson’s Bar & Grill.

Live theater does all of those one better.

The PCLO production of Lady Day, directed by Tomé Cousin, accomplishes what only up-close, in-person theater can provide: a time machine to a specific place and time, sharing the same air with a star turn by a contemporary artist and a real-life legend of yesteryear.


Lady Day at Emerson’s Bar & Grill is at the Greer Cabaret Theater, Theater Square, Downtown, through June 30, 2024. Tickets: For “Removing Barriers” access, visit Note: For the demanding role, Lee will be onstage through 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. 

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