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April 04, 2024

A theater company known for Dungeons & Dragons improv comedy finds a permanent home

SideQuest Theater, formed from the long-running Roll Play show in Philly, plans to expand in its new Rittenhouse space.

Entertainment Improv Theater
SideQuest Theater co-founders seats Provided Image/SideQuest Theater

The co-founders of the SideQuest Theater company have been renovating the Adrienne Theater for a mid-April opening. Pictured, from left, are Kelsey Hébert, Josh Holober-Ward, Cara Hammer and Dominick Arp.

It's easy to tell from Josh Holober-Ward's energy and enthusiasm that he's been doing improvisational comedy since he was a teenager.

During an interview at the Adrienne Theater in Rittenhouse Square, Holober-Ward raved about the progress he and his friends made in revamping the venue for SideQuest Theater, a performance company he co-founded.

"It's a beautiful theater, right?" he said. "It feels like a theater. It doesn't feel like a couple chairs thrown into a box room." 

What is SideQuest Theater?

SideQuest Theater lobby entranceChris Compendio/PhillyVoice

The lobby entrance to the theater now has been updated and decorated to fit SideQuest Theater's origins as a fantasy role-play performance group.

SideQuest Theater originated from Roll Play, an improvised comedy show paying tribute to tabletop role-playing games, namely Dungeons & Dragons. The show came out of his desire to put the silly role-playing antics from him and his local improviser friends on stage, with full costuming and audience participation.

The short-form game-based improvisation, similar to TV show "Whose Line Is It Anyway?" would take audience suggestions and turn them into elements of a long-form fantasy story.

"So whenever (our characters would) cast a spell, it's based on something an audience member wrote, and they have to make it work with what's happening," Holober-Ward said.

Roll Play had its first show at the 2017 Wizard World Comic Con (now called Fan Expo Philadelphia), and it grew a larger audience over the subsequent years. By 2023, the troupe had grown to 17 members with more than 20 shows a year and roughly double the audiences it started with. 

Who is in SideQuest Theater?

SideQuest Theatre renovations co-foundersProvided Image/SideQuest Theater

The four co-founders (Hébert, Arp, Holober-Ward and Hammer) of SideQuest Theater pose for a photo on stage amid renovations.


Joining Holober-Ward in the SideQuest venture as co-founders are three other improv artists with different creative backgrounds. His partner Cara Hammer came into theater relatively late, having a background in biology before taking improv classes and running show production.

Fellow co-founders Kelsey Hébert and Dominick Arp have extensive backgrounds in Philly theater and improv, along with teaching experiences.

Where is SideQuest Theater?

When Adrienne Theater became vacant in June 2023, Holober-Ward jumped on the opportunity to secure a permanent space for the budding SideQuest Theater group. Located on 2030 Sansom Street, SideQuest will be neighbors with Helium Comedy Club and ComedySportz, the latter of which hosted several Roll Play shows.

"We want to take improv and make it feel like theater, and this is the only space we know of that could really do that," Holober-Ward said. "And the only one available — how often do theater spaces just become available, let alone in the heart of Rittenhouse?"

SideQuest Theater seating before afterProvided Images/SideQuest Theater

Pictured above is a before (left) and after (right) comparison of the seating in Adrienne Theater. The seats have been fully reupholstered, and the co-founders are repainting the crests to reinstall them into the seats.


The co-founders and some volunteers spent long nights on the space's renovation. In a tour of the space, weeks before its planned grand opening, Holobor-Ward pointed out that there were still three rows of seats to bolt into the risers in the back of the theater. Each seat was reupholstered and there were piles of the old, worn-out cushions sitting on the stage.

"Tonight is when the stage gets painted," Holober-Ward said. "It's gonna be one of the final pieces." 

What will SideQuest Comedy offer?

Once SideQuest Theater opens on April 12, Roll Play will return for a 16-performance run until May 26. SideQuest will also offer improv and role-playing classes, along with a summer camp for kids aged 11 to 14 to learn improv skills. 

Among the new shows SideQuest will put on are the "Improvised Tony Awards" in June, where performers make up songs on the spot for fictional musicals, and "Weird Weekends" will allow anyone to submit their own experimental one-off shows. Long-term ambitions include starting a role-playing game podcast and filming high-quality specials — and the new theater is equipped for both.

"Those are things we can only do with our own space," Holober-Ward said. 

SideQuest is also having some shows stray away from the fantasy genre. 

"We definitely want to key into role-play with the title with the name of our theater. So SideQuest is very much along those lines, but we want to make it adventurous without specifically being fantasy."

Holober-Ward and his colleagues hope that SideQuest Theater will become a new center for creative storytelling and comedy, and an opportunity to connect more with the community and local theater scene. Renting the space to other groups isn't out of the question, although SideQuest has shows and classes scheduled all the way to January.

"The hope for our theater is that all of our shows are catering to things people are passionate about," Holover-Ward said. "On the main path of your life, this is your side quest to come and have a great time."

What's the deal with fantasy role-play improv comedy?

To Holober-Ward and his colleagues, D&D and improv comedy are a match made in heaven.

"They share a lot of DNA," Holober-Ward said. He described a typical scenario where players are creating a fantastical, imaginary world, but quirky ideas and mistakes slip out, leading the other players to pile on the ideas.

"So if you say, 'Oh, we're in a magical swamp,' and someone says, 'I drink the swamp water.' I go, 'Okay, you do and it tastes like Cherry Cola.' And they're like, 'Oh my god, we found the Cherry Cola Swamp.' And then we've got the elves who run the Cherry Cola Swamp," Holober-Ward said.

The fun comes from growing creative ideas into something incredible and then being able to trace it back to one silly thing that someone else said.

"I love the collaborative creation process. I think it is the spark of all joy and humor," Holober-Ward said. "And it is such a great distillation of what happens when funny, creative, good-hearted people come together to play."

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