Anthony Rapp Brings a Warm, Music‑Driven Holiday Cabaret to Lookingglass Theatre
If your holiday season means cozy camaraderie and quiet reflection rather than glittering pageantry, Anthony Rapp has a message you’ll want to hear. The Tony‑nominated star of Rent and, more recently, Commander Stamets in Star Trek: Discovery, returns to his hometown for a festive cabaret titled Anthony Rapp: Home for the Holidays. The show runs for five performances from Wednesday to Saturday at Lookingglass Theatre, located at 163 E. Pearson St.
The production is a secular celebration featuring six vocalists and three accompanying musicians. In a refreshing departure from traditional Christmas revues, the program includes contemporary and classic favorites such as Joni Mitchell’s “River,” Donny Hathaway’s “This Christmas,” The Beach Boys’ “Little Saint Nick,” and Dolly Parton’s “Hard Candy Christmas.”
While describing the concept to Block Club, Rapp emphasized the goal: to gather in the winter’s chill and, in these challenging times, offer comfort and warmth while honoring the season’s bittersweet edges.
Rapp’s ties to Chicago run deep. Born in the city, he grew up in Joliet and began his career on local stages. He earned Actors’ Equity membership at age nine while touring in the national production of Evita, which lingered in Chicago for months before moving on. His first professional gig was as an understudy for Tiny Tim in Goodman Theatre’s Christmas Carol. Later, as a high school senior, he performed again on the Goodman stage and made his screen debut in Adventures in Babysitting (1987), a Chicago‑set action‑comedy directed by Chris Columbus. Columbus would later direct Rent’s film adaptation, reuniting with Rapp nearly two decades later. Other notable film roles include Dazed and Confused, Six Degrees of Separation, and A Beautiful Mind.
A New Yorker for many years, Rapp has recently relocated his family back to Chicago, settling in Andersonville with his husband, two toddlers, and two cats. “I hadn’t really imagined returning to Chicago until after having kids, but it’s less chaotic here,” he shared. While Joliet remains his sense of hometown, Chicago feels like his roots. He remains a lifelong Cubs fan and, with a Windsor‑like shared misery with the Mets, jokes about a kinship with New York’s baseball rival.
One primary aim of Rapp’s return to the Chicago stage was to reengage with the local theater community thoughtfully. He didn’t want to intrusion but hoped to cultivate meaningful collaborations. After introductions to Lookingglass board members Marci Masur and David Schwimmer, the idea of a music‑centered project gained traction.
In shaping Home for the Holidays, Rapp chose a secular frame. As someone who identifies as an atheist, he wanted to avoid religious songs, though he acknowledges that many seasonal pieces with spiritual origins can be beautiful in their own right. He also recognizes that for many people, December holidays can bring up memories of loss and longing, or simply feel overwhelming in the midst of winter.
Among the repertoire is “Have Yourself a Merry Little Christmas,” a timeless anthem with a history of bittersweet undertones. Originally crafted for the 1944 film Meet Me in St. Louis and rendered by Judy Garland, the song’s enduring message—yet tinged with melancholy—resonates with Rapp’s approach to the season.
Rapp describes the cabaret as a living room‑like gathering: intimate, inviting, and designed to illuminate as much as possible amid the darker days of winter. He hopes the show offers a gentle uplift and a moment of warmth for audiences seeking a little light.
Ticket information for Anthony Rapp: Home for the Holidays is available through Lookingglass Theatre’s website, with performances from Wednesday through Saturday and a Saturday matinee. For details and to purchase seats, visit Lookingglass Theatre’s event page.
Would you welcome a holiday experience that foregrounds secular warmth and intimate storytelling, or do you prefer traditional, religiously rooted celebrations during the season? Share your thoughts in the comments.
