Broadway and Clairton’s Rema Webb Channels Billie Holiday in Homewood Shows

Afro-American Music Institute Presents Pittsburgh-centric ‘Lady Day,’ Based on Vernell Lillie Work


Broadway veteran and Clairton native Rema Webb made her second Pittsburgh appearance this year, both to support hometown musical education institutions.

On March 11, Webb was at Heinz Hall for pal Bill Hartung’s Center for Theater Arts in Mt. Lebanon. This past weekend, she channeled jazz great Billie Holiday in three shows Saturday and Sunday, presented by the Afro-American Music Institute at the Carnegie Library of Homewood. 

Bedecked in elegant black and white, with signature white flowers in her hair, Webb channeled the legendary Lady Day, her performances part of the Bayard Rustin Festival, with events marking the Pittsburgh-filmed movie Rustin’s theatrical and streaming release.

Although the show featured Holiday’s nickname, “Lady Day,” in the title, it should not be confused with Lady Day at Emerson’s Bar and Grill, which is set at that South Philadelphia venue. (Webb appeared in the The Cape Playhouse’s 2021 production). 

Rema Webb in Lady Day at Emerson’s Bar and Grill for The Cape Playhouse in 2021, left, and in the Center for Theatre Arts gala at Heinz Hall in March 2023.
(Images: The Cape Playhouse/Sharon Eberson)

The Lady Day shows in Homewood were based on Crawford Grill Presents Billie Holiday by the late Dr. Vernell Lillie, founder and artistic director of Kuntu Repertory Theatre. In 2000, Lillie adapted her own work, directing a performance by Sandy Dowe at the former Pittsburgh jazz club Dowe’s on 9th. 

Lillie’s play is based on an evening in 1957, when Holiday   was among local jazz legends such as Billy Eckstine to perform at the Hill District’s Crawford Grill, a bustling gathering spot for local jazz legends.

The always busy, New York-based Webb appeared on Broadway most recently in The Music Man, and was an understudy for Fat Ham. Credits also include The Book of Mormon, The Color Purple and The Lion King,

At the elegantly appointed Homewood venue, Webb was supported by New York pianist and music director Gary Mitchell Jr., leading a trio as Billie’s accompanist and as Jimmy – Holiday’s reliable partner in trying to keep her on the straight and narrow.

Webb’s bantered-filled performance as the defiant Lady Day was on point with Holiday’s distinctive boozy, bluesy voice. Billie rejected labels that described her as anything but a  jazz singer, who did it her way.

The show had Webb sharing stories about Billie’s days with band leaders such as Artie Shaw, who would pay double menu prices for his entire band to sit with her in kitchens where restaurants refused to serve Black customers. She remained friends with those musicians, but eventually went out on her own because what she wanted was to walk through the front door.

Webb adorned the persona of Holiday like a glove, pausing at times mid-song to explain her slow and emotional way with tune.  

Rema Webb, center, channels Billie Holiday in a promo for November 19-20, 2023 shows presented by the Afro-American Music Institute.

Songs included No Regrets, the signature God Bless the Child – written for “The Duchess,” her mother – and a moving rendition of Strange Fruit, a song about lynchings in the South that Holiday championed, and which she noted was written by “Lewis Allan, a Jewish school teacher.” Allan was the pseudonym of Abel Meeropol, a member of the communist party who adopted the children of Julius and Ethel Rosenberg, after the Rosenbergs were executed for committing treason.

Webb’s Billie explained the difference between herself and the likes of Ella Fitzgerald and Sarah Vaughan, illustrating how most singers would approach Can’t Help Lovin’ That Man as Kern & Hammerstein intended it, and her way – a distinctly jazzy interpretation.

Billie Holiday’s unique voice and activism made her an apt subject to spotlight for the Rustin Festival and Afro-American Music Institute, which features Jazz on the Loading Dock on Saturdays, 7-9:30 p.m. The center on Hamilton Avenue is in the midst of a capital campaign to expand its physical building and educational reach.

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