Meet the Infamous RLT Stepsisters

Dennis Poole and Tim Cherry have portrayed with flouncy abandon Gertrude and Henrietta, the stepsisters in Raleigh Little Theatre’s production of Cinderella.
by Billy Warden  |  photography Justin Kase Conder

Justin Kase Conder

Before the night is out, one of Raleigh’s most beloved actors will be in tears. Not theater tears. Heartfelt tears that will stun colleagues gathered in a wardrobe room backstage. But that scene plays out later. Right now, Dennis Poole is doing what he’s celebrated for—talking smack and wiggling into women’s clothes. Since 1998, two men, Poole, 59, and longtime pal Tim Cherry, 69, have portrayed with flouncy abandon Gertrude and Henrietta, the stepsisters—judgmental types label them “ugly” and “evil”—in Raleigh Little Theatre’s production of Cinderella. There’s no gig in our enchanted city quite like theirs. Or friendship. Or wardrobe.

“My costume is very pink. Very dainty. Very sexy,” says Cherry, stroking his gray goatee as his eyes drink in this year’s voluminous gown. “But to go to the bathroom after it’s on…ugh.” He then acts out how he must lift layer upon billowy layer. How he must wrestle back the underlying hoop skirt that lends his character her imperial grandness. And finally how he must squirm free of his foundational tights. Cherry turns taking care of the most humdrum human business into an epic, noting with an expert twist of his eyebrows, “When you’re my age, there’s no NOT having to go to the bathroom.”

courtesy News & Observer

“Yes,” Poole hisses. “When you were born, the Louisiana Purchase was still in escrow.” Snap! Onstage and off, the duo is comically at each other’s throats. They portray Gertrude and Henrietta as driven and deluded, absurdly assured of their own magnificence, yet haplessly striving for more.

Backstage, they aren’t much different. Or so it seems at first. In the wardrobe room, as Cherry spins another story, Poole lifts a long pair of scissors high over his head. With a demented smile he glares down at his unsuspecting partner’s jugular. Squint and it’s like watching Bette Davis and Joan Crawford in a sequel to Whatever Happened to Baby Jane? as directed by modern day drag impresario RuPaul.

While Poole, who works in higher education, and Cherry, a potter and retired teacher, make no claim to being social commentators, they do note that interest in their schtick has picked up in the last couple of years. Perhaps that’s just the result of people recognizing their long run. But maybe it’s a sign of a community, intrigued to see themselves reflected in the fractured mirror Gertrude and Henrietta hold up. Maybe, too, the sight of these men unabashedly enjoying themselves as women allows us to consider with a smile changing perceptions of gender. Whatever the modern connotations, the production’s roots go back, way back, before social media. Even before Cherry’s birthday. RLT’s Cinderella draws its inspiration from the English “pantomimes” of the 18th century, wisecracking takes on classic tales, featuring gender bending, over-the-top outfits, songs, and slapstick.

But while it sounds fun, nothing falls as flat as a forced farce—which is why Poole and Cherry are so important. After 260 performances (and 18 more set for this year), they make the manic mechanics seem effortless.

“I don’t have to worry about them; they know what to do,” says director Mike McGee. “They’re 100 percent invested in their roles and they’re just so comfortable. They have the ability to ad lib. They practically finish each other’s sentences.”

Traveling in the same theatrical circles, Poole and Cherry knew each other for years before first stepping into role of the stepsisters. In 1998, the late Haskell Fitz-Simons, the show’s longtime director, watched the two audition separately and was inspired to pair them up. “The most brilliant casting choice of his life!,” Cherry says wryly. “The chemistry was there, and it’s been there ever since.” They both revel in the ridiculous, which helps when scaling the heights of community theater. As Poole gleefully puts it, “I love it when things go wrong.”

Like the time a fire alarm went off during the show. Like the time Cherry’s bloomers came loose and slid off. Like the time a confused stage hand wound up stuck on stage after the lights came up. Through it all, they’ve carried each other. Sometimes literally. “I’m an insecure person,” says Cherry. “But that first year, waiting in the wings, I knew that whatever happened out there, Dennis would fix it.”

Night after night, their antics have continued from the stage to the lobby, where audiences interact with the cast. “You haven’t lived,” Poole says, “until you’ve been backed into a corner by a six year old outraged by the way you treated Cinderella.”


But while fairy tales are timeless, the mere mortals who bring them to life are on a clock. The duo started talking about when to hang up their bloomers way back in the early days. “We’ve always wanted to go out on top,” says Cherry.

They originally thought perhaps they’d bid adieu to the stepsisters after five years, but living a fairy tale has been too much fun to leave behind. “You can come into work in a bad mood, but you talk to Dennis and Tim and you’re ready to party,” says dresser Tana Shehan, widening her eyes. “Those two are wild.”

 But no magic wand can wave away the physical demands of high energy theater. If Raleigh’s signature stepsisters are, in fact, nearing a grand finale, is there anything they haven’t yet shared with each other?  “I’m extremely jealous of you,” Cherry tells Poole, referring to his onstage elan. “Following you in the slipper scene. I’ve never been so miserable in my entire life.”

Poole, sitting a few feet across from his stage sister, takes this in with a grateful smile. Then he glances away and becomes very serious. “I want you to know…” Suddenly, his eyes well up. “You are the most wonderful partner.” And…tears stream down his cheeks. RLT executive director Charles Phaneuf raises a hand to his mouth in surprise, then passes Poole a box of tissues.
“And for you to be my cohort in crime has been one of the most amazing experiences of my life.” Cherry, underplaying things for the moment, simply nods, and the wardrobe room is, for the first time all evening, hushed.

Cinderella is a make believe about lavish balls, royal ambitions, and a glass slipper that sets in motion a happy ending. The real world requires no such trappings to make magic. All that’s needed is a dash of chemistry.

Raleigh Little Theatre’s Cinderella will run from November 30—December 16 at the Cantey V. Sutton Theatre. Billy Warden is the co-founder of strategic communications firm GBW Strategies and the lead singer of the glam rock band, The Floating Children.