Holiday Cabaret is celebratory moment for Theatre Aspen | Arts & Entertainment

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To Theatre Aspen Producing Director Jed Bernstein, what makes celebrating anniversaries special is if you can look back and look forward at the same time, he said. And as Theatre Aspen enters its 40th anniversary, Bernstein looks to do just that.

Kicking off Theatre Aspen’s 40th season is the annual Holiday Cabaret. Returning this year to the Hotel Jerome Grand Ballroom from Dec. 19-23, the cabaret series brings together a talented cast of Theatre Aspen alumni — from professional Broadway stars to local youth performers. They’ve all performed in past mainstage productions.

“The looking back part is pretty easy,” Bernstein said. “And we’re going to accomplish that by doing some favorite songs from favorite shows and including actors who have been with us before and who will hopefully be with us again.”

In looking forward, the producing director continued, Theatre Aspen has already announced its season lineup for the year. He said the organization has never had its entire season already announced by this time of year, and the holiday cabaret event will also serve as a platform for talking about the coming season, as well as for announcing some special anniversary happenings.

It’s a fitting event all around to celebrate the theater company’s past and future. While this marks the fourth year for the cabaret series and its second year in partnership with the Hotel Jerome, the legacy of this cabaret experience goes back to the beginning, Bernstein explained.

Theatre Aspen was in fact born in the Hotel Jerome basement 40 years ago, noted Bernstein, who went on to discuss the history of cabaret culture as it relates to resorts like the Jerome.

“In olden times, people would go to these resorts, whether it was a ski resort or sun resort, and there would always be a show in the hotel, usually a nightclub act, and at least one night during your visit, you and the family would go to the show in the hotel,” Bernstein said. “And so this is kind of a call back to those times too, where the social center of town — which, in our case, Main Street and the Jerome — has entertainment every night for that week.”

Across the five performance nights, patrons will first enjoy a seated chef’s dinner, starting at 6:30 p.m., followed by the hour-long musical production featuring Broadway and holiday classics performed by the Theatre Aspen cast.

While last year’s showcase was more holiday-oriented, with this year being the first anniversary cabaret, the entertainment will lean a little more toward the Broadway acts, Bernstein said.

He emphasized how this year’s cast together have multiple Theatre Aspen mainstage credits among them. For the cabaret, these ­alumni actors will be recreating some of the numbers that they’ve performed in past shows with Theatre Aspen.

Among the cast is Jayke Workman, who was seen this past summer in both Theatre Aspen’s “Gypsy” and “Jersey Boys” and the summer before as Mary Sunshine in “Chicago” — which led to the actor’s Broadway debut playing the role in New York.

Workman said he was thrilled when Theatre Aspen asked him to be a part of the company for this year’s cabaret and expressed how special it is to get to revisit some of the tunes he’s performed over the past two summers with his fellow cabaret cast members.

“Since we’ve all done multiple shows at Theatre Aspen, we have a bit more of a repertoire of songs to choose from,” Workman said. “The audience will recognize songs from past productions — it’s like the greatest hits of Aspen’s musical past, and also some fun new surprises, as well.”

Workman said he’ll be singing some of his Mary Sunshine material and explained that due to the intimate nature of the cabaret, it will look and feel much different than his on-stage performances.

“It’s going to be different for sure — it’s less of a divide between myself and the audiences, both physically and because I won’t be fully in character,” Workman said. “It gets to be more intimate.”

Cast member Galyana Castillo also spoke of the intimacy surrounding the cabaret. Castillo worked alongside Workman in Theatre Aspen’s “Chicago” and has also been seen in the company’s mainstage shows: “Guys and Dolls,” “Little Shop of Horrors” and “Rock of Ages.”

“As it is, Theatre Aspen productions are pretty intimate, and the cabaret setting allows for more person-to-person, eye-contact with the audience,” Castillo said. “It feels more personal than it already is working with Theatre Aspen in the summer.”

For both Castillo and Workman, working with Theatre Aspen in the summers has made great impacts on their careers, they said.

Castillo expressed how there’s a sense of comradery and community built among the cast and crew throughout each Theatre Aspen production that she’s been involved with. And Workman can attest — the actor said he’s formed many crucial relationships through Theatre Aspen and those relationships have continued to prosper back in his home in New York City.

“It’s had a huge impact on my career, working alongside some of the industry’s most incredible creatives,” Workman said. “And especially that it’s in Aspen — Aspen is its own bubble but then you come back to the city and have this rich group of contacts and friends.”

It’s this familial atmosphere described by Workman that Theatre Aspen has been fostering since its start. And for Bernstein, he hopes the notion is even more so felt with this year’s holiday cabaret.

“Theater Aspen should be a place that you always feel connected to and you always feel like you could return to — we try to foster that sort of atmosphere,” Bernstein said. “And with the addition of the holiday cabarets — which, you know, certainly the holiday is a family time — we want these actors to feel doubly a part of the family.”

Joining Workman and Castillo as part of the cabaret family is Kimberly Doreen Burns (“Ragtime” and “Our Town”); Trevor James (“Jersey Boys”), Isaiah Reynolds (“Hairspray”) and Beth Malone (“Les Misérables,” “Spelling Bee” and “The Marvelous Wonderettes”).

Malone, a Tony Award nominee and local resident who partakes in numerous productions throughout the valley, has been a part of the Theatre Aspen family since 1999.

This year’s Holiday Cabaret is directed by ­stalwart Theatre Aspen director Mark Martino, with music direction by Eric Alsford. New this year, local youth alumni of Theatre Aspen productions will be performing alongside the professional cast of actors each night.

The holiday cabaret will take place Dec. 19-23 at the Hotel Jerome. Tickets can be purchased at