Interludes

VIEWPOINTS – Nights at 54 Below: Veterans CHESTER GREGORY and LIZ CALLAWAY claim their spots in the Broadway pantheon

• By drediman
• September 8, 2025
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No doubt about it, Broadway is a tough business — competitive and often times subject to the inexplicable whims of a finicky public. Last week, I had the great pleasure of twice frequenting the Theater District cabaret venue 54 Below to catch two musical theater veterans emphatically make claims for their respective spots in the Broadway pantheon. As always, read on for my thoughts.

THE WIZARD AND I: LIZ CALLAWAY SINGS STEPHEN SCHWARTZ
54 Below

Is there a more perfect match than the pairing of beloved cabaret star Liz Callaway and legendary Broadway composer/lyricist Stephen Schwartz? Based on seeing Callaway’s recent stint at 54 Below — appropriately entitled The Wizard and I: Liz Callaway Sings Stephen Schwartz (RECOMMENDED) — I’d be hard pressed to dispute the claim. Over the course of the evening, the easy going and good natured singing actress took her adoring audience through an overview of songs from Schwartz’s iconic musicals — with particular emphasis (unsurprisingly) on Godspell, Pippin, and Wicked, in addition to the requisite medley concocted from his larger output — as well as recounted her close personal friendship with him (Schwartz even wrote a song specifically for her, “Fearless”, which Callaway put over with tremendous affection). With its perfect pitched belt, her voice is just as clarion as when she was one of the indisputable go-to musical theater ingenues of the 1980s and 1990s. She’s also found a disarming way of emoting songs with refreshing honesty and directness, which was especially affecting in more introspective songs like “Beautiful City” from Godspell and “Finale/With You” from Pippin. She concluded the evening with one of her signature numbers — and one of the composer/lyricist’s most accomplished and stirring compositions — “Meadowlark” from one of the rare Schwartz misfires The Baker’s Wife (coincidentally, the musical is being revived this fall at Classic Stage Company starring none other than Ariana DeBose). For her encore, Callaway left audiences with a gently caressing rendition of the bittersweet song “For Good”, one of the most recognizable songs from the juggernaut Wicked.

CHESTER GREGORY: BLACK ON BROADWAY
54 Below

Then there was the supremely talented Chester Gregory, whose thrilling 54 Below show Black on Broadway (HIGHLY RECOMMENDED) was an emotional and musical journey of the highest order. In essence, the show charted the evolution of Gregory’s professional career vis-à-vis his personal challenges, namely as it relates to familial, confidence, and vocal issues. Gregory, with his immense charisma and soaring and soulful vocals, was pegged for greatness early on in his career, garnering significant attention when he played, at a tender age, the iconic title role in The Jackie Wilson Story at Chicago’s Black Ensemble Theatre (it’s a portrayal that he repeatedly returned to, in various different iterations, over his long career). From there, he was off to the races, booking New York gigs in such high profile musicals as the Tony-winning Hairspray, Disney’s Tarzan, a successful revival of Dreamgirls, and the stage version of Sister Act — a period of time only marred by a distasteful experience with the development of the musical adaptation of Shrek. After subsequently navigating and working through personal demons — particularly as it related to dealing with others’ expectations of him as a performer — Gregory triumphantly returned to Broadway in the central role of Berry Gordy in the return engagement of the crowd-pleasing jukebox musical Motown. This portion of the show showcased his newfound gravitas, as manifested by a devastating performance of Marvin Gaye’s “What’s Going On?” and a exuberantly heartfelt rendition of Smokey Robinson and Ronald White’s “My Girl”. Gregory’s show took on even more resonance as he stepped further out from under the veil of musical theater, putting the focus squarely on himself. Indeed, he ended the night with a number of songs he wrote himself — “To Be Loved”, “Zodiac Killer”, “Let’s Be Together” — completing his hard-won journey to his present self in a totally satisfying, cathartic manner.