Richard Skipper Celebrates! Life Lessons from Legends
The Arts Project of Cherry Grove Presents:
Richard Skipper Celebrates! Life Lessons from Legends
Celebrating the legends, trailblazers, and unforgettable personalities who helped shape Cherry Grove’s extraordinary history!
With Michael McAssey on Piano and Special Guest Star, Cherry Grove’s Own Legend, Rose Levine
On Thursday, September 10, 2026, at 7:00 PM, award-winning entertainer, host, author, and LIVE ENTERTAINMENT historian Richard Skipper returns to Fire Island for the first time in twenty years with his acclaimed new show, Richard Skipper Celebrates! Life Lessons from Legends, at the APCG Community House in Cherry Grove.
This engagement marks a deeply personal homecoming. Richard’s last performance on Fire Island was more than two decades ago—when he was appearing as Carol Channing, a role he performed around the world for twenty years. This time, he returns as himself, sharing the stories, songs, humor, and wisdom gathered throughout a lifetime spent celebrating the artists who shaped American entertainment.
“It’s fitting that this return takes place in Cherry Grove,” says Skipper. “The last time I was on Fire Island was to see Carol Channing perform alongside Justin Vivian Bond. Those memories have stayed with me, and returning now with this show feels like coming full circle.”
Joining Richard is Rose Levine, recognized by Guinness World Records as the world’s oldest continuously performing drag queen. For more than seventy years, Rose has been a beloved entertainer and cultural icon whose career has become inseparable from the rich history of Cherry Grove and Fire Island. Her remarkable life embodies resilience, artistry, humor, and authenticity—the very qualities celebrated throughout the evening.
Unlike a traditional cabaret performance, Richard Skipper Celebrates! Life Lessons from Legends is an audience-interactive experience. Before the show begins, audience members are invited to submit questions. Those questions shape the evening, making every performance unique. Through songs, stories, laughter, and spontaneous conversation, Skipper explores the wisdom passed down by legendary artists including Carol Channing, Jerry Herman, Julie Wilson, Marilyn Maye, Lee Roy Reams, and many others, while celebrating the legends sitting in the audience.
“My career has never really been about celebrity,” says Skipper. “It’s about the lessons people leave behind. Every great artist I’ve known has taught me something—not just about performing, but about living. Those are the stories I want to share.”
Known for his warmth, wit, and extraordinary ability to connect with audiences, Richard Skipper has appeared at venues across the country, including 54 Below, The Laurie Beechman Theatre, The Green Room 42, The Revolution Stage Company, Maureen’s Jazz Cellar, and many others. His extensive oral history project, CallonDolly.com, contains more than a thousand interviews documenting the enduring legacy of Hello, Dolly! and the artists who brought it to life.
As Fire Island continues its proud tradition of celebrating individuality, artistry, and community, this special evening promises to honor not only the legends who came before us, but the life lessons that continue to unite us.