Pittsburgh CLO's 'Lady Day' is a beautiful, raw evening spent with a legend

Billie Holiday will undoubtedly — and deservedly — be a household name for generations to come.

The revered jazz singer was just 44 years old when she passed in July 1959. “Lady Day at Emerson’s Bar and Grill,” the first musical of Pittsburgh Civic Light Opera’s summer 2024 season, takes place just months before her death — and takes a challenging-but-beautiful look at the life of a legend.

“Lady Day” is considered a jukebox musical, as it contains pre-existing music not written for the show. In this case, the songs are mostly Holiday’s own (or ones that she performed). It was written by Lanie Robertson and premiered in Atlanta in 1986. It opened on Broadway in 2014. Pittsburgh CLO’s production takes place at the Greer Cabaret Theater in Downtown — a perfect venue to immerse the audience in the musical’s world.

The show is set at Emerson’s Bar and Grill (as the title suggests) in South Philadelphia. Having a space that is set up as a cabaret, complete with food and drinks (ordered before the show), transports the audience to a night with Holiday in 1959.

But “Lady Day” isn’t just a mellow string of jazz standards. With the amazing effort of Gabrielle Lee as Holiday, the audience glimpses the not-always-perfect side of show business. Though the performance happens in real time, mimicking an actual 90-minute set, the show is a chronicle of Holiday’s life as told by her. In between crooning and belting out a knockout set list — including “What A Little Moonlight Can Do,” “Strange Fruit” and “Crazy He Calls Me” — Lee delivers the humorous and harrowing stories of Holiday’s life.

Lee’s singing voice is lovely and favors Holiday’s enough to be immersive without seeming like an exaggerated impression. The most remarkable part of her performance, however, is her ability to convincingly act progressively more and more intoxicated as the show goes on. Holiday died due to severe health issues caused by cirrhosis of the liver just months after the show’s setting, and her late-in-life substance issues are written heavily into the script.

Lee also possesses that unique “star quality” that makes her impossible to look away from, even in the most difficult moments.

“Lady Day” has Holiday telling stories of her childhood, being a musician in the time of widespread racial segregation and her past loves. The stories are at times hilarious, at times heartbreaking — yet always riveting. Toward the show’s beginning, she comes down from the stage and walks through the audience, interacting with the crowd here and there, in a manner that manages to feel spontaneous.

Music director Kenney Green-Tilford also has a few lines as Holiday’s accompanist Jimmy Powers. And Pittsburgh CLO’s band — bassist Paco Mahone and percussionists James Johnson III and David Hanson — add lush life to Holiday’s tunes.

Tomé Cousin’s direction brings the show’s clear and captivating vision to life.

There is one other cast member who can’t be forgotten — or furgotten. Scrappy Mason plays Holiday’s dog, Pepi. No notes whatsoever.

The technical aspects of “Lady Day” were impeccable, especially in their simplicity. Lighting designer Andy Ostrowski used all of the venue’s tools to set the mood. The scenic design by Holly M. Fleischer felt lived-in, just like the stage of a 1950s nightclub would be. Claudia Brownlee’s costume design and Tenel Dorsey’s hair and makeup design were beautiful.

“Lady Day” is an excellent opener to CLO’s summer season. It’s a raw, sometimes tragic, but a beautiful journey through the music and life of a legend.

And the dog is adorable too.

“Lady Day at Emerson’s Bar and Grill” runs through June 30 at the Greer Cabaret Theater in Downtown Pittsburgh. For more information and tickets, visit pittsburghclo.org. Starting June 1, Ayana Del Valle will play the role of Billie Holiday on Wednesdays and Saturday matinees.