By JESSICA NEU
Late-night shows at the Greer Cabaret Theater can be unpredictable and sometimes even downright rowdy. The alcohol is flowing, the audience is ready to participate, and artists find the perfect pocket of hilarious self-deprecating jokes, edgy political commentary, and pull out all the ‘bangers’ from their repertoire.
However, sometimes the Cabaret’s final performance brings the season to a slow, gentle, emotional conclusion. This happened with Norm Lewis’ captivating performance in May 2023 and again with the delightful Laura Benanti in 2025. Broadway star, actor, and singer Cheyenne Jackson’s performance last night matched wits, talent, and emotion with his season-concluding predecessors.
Before taking the stage, Jackson declared that “every show should have a proper overture of songs that shaped and molded [the performers] into the artists [they are] today.” Jackson’s overture included snippets of the theme songs from Charlie’s Angels, Magnum PI, Little House on the Prairie, and, of course, Entertainment Tonight. From the back of the house, Jackson then made his way to the stage while belting out a rendition of Nina Simone’s “Feeling Good” that was similar to crooner Michael Bublé’s 2005 version. Once on stage, Jackson explained that this performance would be an “amalgamation of shows he’s done before” and a tale of “how a super tall, super Christian, super queer kid from the most conservative part of northern Idaho” can make it in the entertainment industry. Jackson spoke of his humble beginnings in northern Idaho. Living with his mother and father, the family did not have running water for several years and lived with their pet goats, Melody and Harmony. One fateful day in high school, Jackson’s French teacher announced that the national Broadway tour of Les Misérables would be coming to Spokane, Washington. At that time, Jackson had never heard of Broadway and had never been to Spokane. However, within minutes of the curtain rising on Les Misérables, Jackson quickly knew what he wanted to do for the rest of his life. “I didn’t know that was available to me,” Jackson told the audience. “I never related to the kids my age in Idaho. I felt like I belonged while watching Les Miz. I’m supposed to be a singing prostitute on Broadway.”
With his pitch-perfect tenor, Jackson beautifully transitioned into “Something’s Coming” from West Side Story. And something certainly was coming for this super-tall, queer, Christian from Idaho. After joining a gay youth group that had just sung Indigo Girls songs, Jackson began auditioning for community theater in the summer of 1995. Jackson also fell in love for the first time during this “never-ending summer” and had his first relationship with a man. The relationship ultimately failed when his lover decided to marry his female fiancée, but the story eventually reached a happy ending. Without missing a beat, Jackson punctuated the tale of his first love with Chappel Roan’s “Good Luck Babe,” proving that he sounds just as stellar singing Top 40 hits as he does classic Broadway or jazz numbers.
Jackson’s love for his husband and nine-year-old twins exuded as he shared heartwarming stories of his time spent as a dad. Anecdotes about his children not being gay but still wanting to attend the Pride Parade provided the perfect segue for Jackson to talk about his own father, whom he lost suddenly at the age of 70. Jackson spoke candidly of his grief process, encouraging audiences to “read the sad letters and listen to the old albums” from their own lost loved ones. This relatable advice made Jackson feel even more authentic and approachable than he already was.
Returning to the crooner genre, Jackson entertained audiences with his rendition of Harry Connick Jr.’s “A Wink and a Smile” before talking about his dear friend, the late Gavin Creel. Jackson served as Creel’s understudy in Thoroughly Modern Millie. He told a story of the two preparing a duet to perform at NYC’s famous cabaret club 54 Below. Jackson asked Creel if he would sing Adele’s “When We Were Young” with him. Creel agreed, but wanted to make the arrangement. I am fairly certain that no one in the audience was prepared for what came next. Jackson played a saved voicemail of Creel singing the freshly arranged Adele song. Some audience members wept, some sat in disbelief, some held hands. Creel’s tender voice pierced each corner of the theater, and he counted Jackson in, who finished the song live.
Jackson brought the tempo up after that emotional moment with Elvis’ “A Little Less Conversation” before returning to storytelling. He amused audiences by explaining that he “contracted a wild case of the fuck its.” This attitude propelled him to read some of his old, negative theater reviews that claimed he delivered lackluster performances and lacked comedic timing, all while singing Frank Sinatra’s “That’s Life” and Dean Martin’s “Besame Mucho.”
Jackson also paid a beautiful tribute to another dear, departed friend, Leslie Jordan. Jackson stressed the importance of continuing to talk about and tell stories of those we have lost before belting out Donny Hathaway’s “A Song for You” with heartfelt veracity and vulnerability.
Jackson executed the laid-back crooner numbers with sophisticated ease, and his stories carried an emotional vulnerability and relatability that made his show the most memorable in quite some time. As powerful as his posthumous duet with Creel was, a story of his father told toward the end of the show was just as meaningful. Jackson spoke about how coaches tried to recruit him to play football when he was younger, but he preferred being in the show choir. His father took him to watch a football practice, which Jackson found violent and unappealing. In that moment, his dad assured him that he did not have to play football. He then sang an original song about his father’s acceptance of Jackson’s sexuality. With the lyrics, “he just smiled and put his hand on me and said it’s ok, you are gentle, it’s ok, you are kind, that you don’t want to play like them, you’ll be fine.” I cannot help but feel that these beautiful lyrics must have been immensely therapeutic for many members of the audience, not just last night, but every time Jackson sings this original piece.
He concluded by reminding us to “become the most authentic version of ourselves because we need it” before a gentle encore of Jason Robert Brown’s tenaciously optimistic ballad, “Hope.” We exited the theater, wiped away our tears, drove home, and awoke this morning with new memories, perhaps a gentler approach to others, a slightly more open heart, and a little more hope.
Details on the Pittsburgh Cultural Trust 2026-2027 Trust Cabaret series can be found at https://trustarts.org/pct_home/events/series/trust-cabaret-series/shows
Jessica Neu holds a PhD in Rhetoric and is part of the Communication Department at Carlow University.
Categories: Arts and Ideas
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