Josh Shaffer

These 2 men in drag have been favorites of the Raleigh holiday season for decades

They’ve been ugly stepsisters for 20 years: Raleigh’s favorites from 'Cinderella'

Raleigh Little Theater's Tim Cherry and Dennis Poole have played the role of Cinderella’s conniving stepsisters for 20 years, making them the favorites in one of Raleigh’s longest-running holiday shows.
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Raleigh Little Theater's Tim Cherry and Dennis Poole have played the role of Cinderella’s conniving stepsisters for 20 years, making them the favorites in one of Raleigh’s longest-running holiday shows.

For the past 20 years, the same two men have smeared on pudding-thick makeup, pulled on towering wigs and transformed into a pair of beloved she-devils: the ugly stepsisters of “Cinderella.”

Since 1998, Tim Cherry and Dennis Poole have perfected the most scene-stealing roles in Raleigh’s holiday favorite, swaggering across the stage in circus-tent gowns, arching their eyebrows with exaggerated haughtiness, scheming and plotting in spectacular drag.

The two actors have spent so many nights portraying Henrietta and Gertrude at Raleigh Little Theatre – 260 at last count – that it is hard to imagine anyone else in their extra-large pumps.

So many people in the Triangle have watched them onstage – 100,581 at last count – that they sometimes get recognized, in civilian clothes, by children at Kmart.

So now, after two decades in the same spotlight in one of Raleigh’s longest-running shows, they reflect on what makes them an enduring and cross-dressing holiday staple.

Poole, aka Gertrude: “A lot of guts and a lot of makeup.”

In real life, no one would accuse either man of over-the-top behavior.

Cherry, aka Henrietta, spent many years teaching elementary school art. Retired at 68, he teaches pottery classes at Sertoma Arts Center and keeps a 6-inch goatee, vowing in vain to exercise before the show starts.

Cherry: “I am the daintier of the two stepsisters, and I’m currently the heavier of the two stepsisters. So we have to suspend our disbelief. But I am the most beautiful stepsister. That is in the script.”

Poole: “You’re also the most delusional stepsister.”

‘Golden Girls’

Poole, the youngest at 58, worked many years for the state College Foundation, and he fashioned his performance partly out of his “Golden Girls” fandom.

Poole: “I ask myself, ‘How would Betty White say this line as Rose Nylund?’ Poor Gertrude is just an idiot, and I found that look. That bug-eyed, slack-jawed look I do.”

Cherry: “Honey, you had that.”

Both actors dabble in other RLT projects. Cherry played Sir Galahad’s mother in “Spamalot,” adding to his drag repertoire. Poole has helped raise tens of thousands of dollars during the cabaret fund raiser, in which he auditioned, unsuccessfully, to be the theater’s “diva.”

But in a show that some families attend every year going back decades, they own the longest run by far. Cherry missed one year with a back injury, a glitch no one counts because, as Poole described it, “Cinderella” without him felt like a table with three legs.

“They’re these really outrageous men in drag who are chewing the scenery,” said Charles Phaneuf, RLT’s executive director. “That’s why it’s memorable.”

Along the way, they’ve lost wigs onstage. Poole once played Gertrude with bronchitis, his voice dropping an octave until he sounded more like Bea Arthur than Betty White.

But they still audition every year, never considering themselves a lock for the parts, fussing at each other in the off-season.

‘Like sisters’

Cherry: “Dennis and I are very much like sisters in our off-time. Battling. We insult each other.”

Poole: “That’s our warm-up. We warm up all year long.”

More than once, Cherry has decided that this year will be his last. But on that year’s final show, taking his last bow, he can’t walk away. It feels too good being part of something that inspires such loyalty.

The feeling continues in the lobby, where the two sign autographs and get fawned over by whole families – one of which hasn’t missed “Cinderella” in three decades.

And sometimes, starstruck children in the lobby will ask the big question, the 300-pound pumpkin in the room.

Poole: They walk up to me and say, ‘Are you a boy?’ Sssh. They won’t let me do the show anymore.”


When: Thursdays to Sundays from Dec. 1 to Dec. 17.

Where: Raleigh Little Theatre on Pogue Street in Raleigh.

Tickets: $27 for members, $28 on opening weekend and $33 otherwise. Tickets can be bought at or from the box office at 919-821-3111.