The Strand Theatre in Oak Bluffs has had many lives since its founding more than 100 years ago but perhaps none more vibrant than today, thanks to the passion and vision of the seasoned entertainment promoter Steve Capers and his wife Dorothy. The couple took over the historic space in 2022 after it languished empty during the pandemic years. In addition to showing films in the beautifully restored 214-seat moviehouse, the Capers host local musicians and songwriters at off-season Strand Jams. In August, eager fans flock to the Martha’s Vineyard Comedy Fest stage where comedian Damon Williams hosts a line-up of top comedic talent. The Capers’ latest additions to the Strand include a coffee bar in the lobby and a state of the art podcast studio upstairs. Steve and Dorothy Capers are two of the Island’s most passionate impresarios, with a mission to provide entertainment experiences and a special place of community. I visited with Steve on a sunny July day as he ushered families into their seats for a Vineyard rite of passage – a screening of Jaws. His wife and business partner Dorothy was off-Island.

Q. What led you and your wife to create Martha’s Vineyard Comedy Fest?

A. I used to work for Comedy Central where I had the opportunity to work with the Dave Chappelles of the world — Louis Black, Jon Stewart, The Farrelly Brothers and many, many of these comedians. When I left, I started Knock-Knock Comedy Productions and from there started doing shows across the country. Martha’s Vineyard was a vacation spot for us and it was my wife who said, ‘Steve, you should do comedy shows here. Just try and if it doesn’t work, at least you can say you tried.’

Q. How did you get started?

A. In 2011 we did a whole grassroots approach. I was at Inkwell Beach passing out flyers, walking up and down Circuit shaking hands, kissing babies. I knew I could sell myself and then I could sell the comedy shows.

Q. How did Dorothy support the cause?

A. Dorothy was involved with the Polar Bears and The Cottagers and they recognized her as “the comedy lady.” Dorothy is more the socialite – she’s the hostess with the mostest. Together we just kept networking and networking and they started coming to our shows and by year five, we were selling out!

Seasoned entertainment promoter Steve Capers and his wife Dorothy have leased the Strand Theatre in Oak Bluffs to show movies (including regular showings of Jaws.) Jeanna Shepard

Q. What led you and your wife to land the Strand as a venue?

A. We used to be at the Lampost where we had some really good shows. The comedians could feel the energy, being right on top of the audience. It was hot and steamy, the air wasn’t working, but the people came and laughed. We had done a few shows at the Strand and then Covid hit. So we bounced around and when the Strand was still available, it was my wife, again, who said we should just give it another try.

Q. Who is this year’s biggest headliner at the Martha’s Vineyard Comedy Fest?

A. This is our 12th annual comedy fest and no doubt it would be D.L. Hughley. He was one of the original Kings of Comedy. He had the Hughley Show on ABC. This is his first time on Martha’s Vineyard. Tickets to his shows [Hyatt Presents D.L. Hughley One Night Only] sold out in three hours.

Q. Is it easy to attract talent to the Island?

A. With our comedians, we position it as a working vacation. You’re a big fish in a small pond and we want you to enjoy the food, the culture, the music and then, by the way, come to work. We get so many comics calling us to get on the line-up. It’s a pretty selective process.

Q. Did you ever pursue a career as a stand-up yourself?

A. No, I have not been a stand-up comedian, but people say I have the mindset of a comedian. They have the guts and the courage to go on stage and they know how to turn their frustrations into an art form to make us laugh. I’m more spontaneous. My feelings would be hurt if you didn’t laugh at my joke and I still had to stand on stage! Damon Williams is the face of the festival and I’m behind the scenes.

Q. What are your plans for the coffee bar in the lobby of the Strand?

Steve Capers also plans to operate a podcast studio above the theater Jeanna Shepard

A. Our strategy is to open early in the morning and offer coffee from a different country each week — Guatemala, Peru, Brazil. It’s a grab and go but if you want to stay, we’re going to put on daytime television in the theatre, to have a different experience – all to generate revenue to keep the theatre going. This is an expensive project, to say the least. You could even use this place to have a wedding. We have a beautiful aisle, the stage. We’re just trying to get real creative.

Q. Tell me about your investment in a podcast studio upstairs.

A. This building – this theatre – is so tied to the community, so we hear stories. One lady said she was the popcorn girl growing up, so she was thrilled. Our projectionist? His grandfather used to run the projection back in the day. We want to document this sort of stuff. We want to be a permanent fixture in Oak Bluffs and on Martha’s Vineyard. We’re going to start building content so we can create the Strand Theatre podcast. We just want to hear these stories and we want it to be professional.

Q. What’s next for the Strand?

A. Staying community focused. That’s huge. We know that it is the community that is going to lift us up. We take pride in that. There’s a lot on our shoulders, but people have been knocking on our doors saying, thank you, thank you, thank you.

Sissy Biggers is a regular contributor to the Vine and a frequent contributor to Martha’s Vineyard magazine.