Alexis J. Roston, a Black woman, portrays Billie Holiday. She is wearing a sleeveless white formal gown with a gardenia in her hair and long beaded white fingerless gloves. She is standing in front of an old-fashioned microphone, caught mid-song.
Alexis J. Roston as Billie Holiday in Lady Day at Emerson's Bar and Grill at Mercury Theater Chicago's Venus Cabaret Credit: Liz Lauren

Alexis J. Roston’s sixth go-round playing jazz legend Billie Holiday in the last year of her life is beautifully layered, heartbreaking, and still affirming of the great vocalist’s accomplishments, against a multitude of odds. After a decade on and off in the role, Roston is now a codirector in Mercury Theater’s production of the Lanie Robertson one-act Lady Day at Emerson’s Bar and Grill; she’s said her lived experience (having now lived longer than Holiday) informs her matured approach to the role. Set in the Mercury’s intimate Venus Cabaret Theater, the venue replicates a small club in Philadelphia, one of the only places left for Holiday to perform after her New York City cabaret card was revoked. After some waiting around, we’re told “Ms. Day is on her way, they wouldn’t let her through the front door,” and she eventually barges backstage, big coat and dog in tow.

Lady Day at Emerson’s Bar and Grill
Through 3/12: Fri 8 PM, Sat 3 and 8 PM, Sun 3 PM, Mercury Theater Venus Cabaret, 3745 N. Southport, 773-360-7365,, $60-$70 (premium tables for up to four people $259-$299, including a bottle of sparkling wine)

What follows is a magnetic greatest hits concert, where gorgeous vocal performances of songs like “When a Woman Loves a Man” and “God Bless the Child” are interspersed with the sad and rueful storytelling of a woman who faced unimaginable racism, sexism, and trauma throughout her short life. While an intentionally “off the rails” performance due to the performer’s addiction and mental health could lead to voyeuristic pity, Roston’s sparkle and vulnerability create room for empathy and admiration for Holiday, who is still standing and singing despite it all. You leave wishing Holiday knew her legacy and feeling deeply unsettled by how songs like “Strange Fruit” are still so topical.