The Best of Ann Hampton Callaway show, similarly to the last time I saw her at 54 Below in 2023, was somewhat cobbled together from Callaway’s other performances. Not that a “best of” cabaret necessarily needs an additional theme, but I felt like I was missing out on the other projects she frequently referenced in the patter—and I wondered what, specifically, she wanted to share in our time together. As a seasoned professional, Callaway has vocal virtuosity, stamina, and stage presence for days, but the emotional “why” of it was less clear that night.
Opening with “Our Love is Here to Stay” (George and Ira Gershwin), Callaway set the tone with swagger and a scat solo. She tastefully kept the scatting to this opening number, which worked very well for the evening’s varied repertory. Music Director Ted Firth led the band on piano, with Dean Johnson on bass and Tim Horner on drums; they were an incredibly skilled group of musicians playing polished and imaginative arrangements. Callaway’s version of “Desperado” (Glenn Frey, Don Henley) was a lovely homage to Linda Ronstadt’s heartfelt cover, perhaps with a bit of a wink to the campiness of the original Eagles’ version. The ever-timely “Big Yellow Taxi” (Joni Mitchell) was lively and driving, and somehow Johnson impressively managed to get something like a Jaco Pastorius-inspired fretless Fender sound out of his standup bass. A medley of “People” (Jule Styne, Bob Merrill) and “Being Alive” (Stephen Sondheim) was well paired musically and thematically, and Callaway put conviction behind both songs’ human stories. With some introductory comments about Carole King’s legacy and the power of vulnerability in performance, “Will You Love Me Tomorrow” (Carole King, Gerry Goffin) was beautifully stripped down, with soft mallets on the drums and the piano arrangement showing more harmonic depth than in The Shirelles’ or King’s versions. But given Callaway’s invitation to vulnerability, I wanted to hear something even more grounded, where the diva stepped aside for a moment and let us in.
I was left that evening wanting to connect with a different part of Callaway’s artistry. I loved her running schtick about her ex-husband; the silliness of the bit still lands. She’d periodically allow herself a goofy pun, riffing on a name or a random word, and her sense of humor came across so genuinely and intelligently. Her confident diva side is great as well, and it’s very well earned from decades of award-winning creative output. But the patter felt sentimental, such as when the audience was encouraged to be excited at the question of who had been inspired by Barbra Streisand. When you have written music and lyrics for so many legends, as Callaway has, famous name references are fair game, but I felt like we were often unnecessarily in the world of recycled cabaret tropes for a fan-based audience. In the hands of a less capable artist, this would simply be a performer’s best, but in her case, there’s a depth of character and skill that I would have enjoyed seeing front and center.
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Presented at 54 Below, 254 W. 54th St., NYC, Sept. 25 & 26, 2025.
Penelope Thomas is a performer, writer, and communications consultant. Credits include lead vocals for two albums with prog rock band FauveMuseum; background vocals with Shellen Lubin, and US & UK tours of Mikel Rouse’s 'The End of Cinematics.' She’s read poet Anne Carson’s work at The Whitney Museum and played leads in HBO Women in Comedy Festival-selected film Pretty Dead and the upcoming indie film, "The Interview." She studied voice with Norma Garbo, music theory with bassist Mark Wade, LoVetri Somatic Voicework through Baldwin Wallace University, and acting with Deena Levy. She taught in the New School’s Sweat musical theatre intensive. With a degree in Cultural Studies & Anthropology and a background in contemporary dance, Penelope loves thinking and writing about performance—connecting the dots between styles and genres and supporting the connection between artists and audiences.
