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Theater Spotlight: An Interview with Infinity Theatre’s Founders Alan and Anna Ostroff

Jul 14, 2015 10:05AM ● By Cate Reynolds
By James Houck

Husband and wife dynamic acting duo Alan and Anna Ostroff honed their thespian skills performing in many productions on stages throughout the country. When they finally settled in New York City, they stood behind the curtain as producers, directors, and writers. With many credits to their names, including a Tony Award for the Broadway revival of Pippin, their success was qualified. Six years ago, the Ostroffs embarked on a new endeavor in a new location. They collated their entire skillset and founded the Infinity Theatre Company in Anna’s hometown of, none other than, Annapolis. We spoke with the couple about the company’s direction and local performing arts in advance of their summer season, which includes performances of Baby: The Musical, July 11th–August 2nd, and Jack vs. Rapunzel: The Musical, continuing through August 1st.

With Infinity now entering its sixth season, do you find that the Annapolis community has embraced live theater at the level you originally envisioned?

Infinity has long-term goals for Annapolis. We aim to institutionalize theatre into the town’s DNA, just like sailing, the Navy, history, and the Bay. That will take more years of producing the right shows in the right way, but at this point, we are thrilled with the support of the community, who filled 7,000 seats last summer. We already have more than 500 subscriptions purchased in advance for the upcoming season, so we might just achieve “The Impossible Dream.”

What have been some challenges of starting and maintaining a theater company?

Our biggest standing challenge is the talent import process. While we do have local auditions every year and employ some of the area’s theatre artists and technicians, most of the team is from New York City. We hand select everyone, which takes months. During our busiest times—our tech weeks which end with our opening weekends—we bring as many as 25 people from NYC to Annapolis. The logistics of this are very complex. But we have a great team, very flexible, and we are getting more donated housing for the city slickers we bring down, which helps defray this massive expense. Other than that, we have run the gamut of challenges of starting an endeavor of this size and quality.

Have you had to compromise between budget and quality of production? How is balance maintained in this market/demographic?

It is maintained by audience reaction. Anna and I can confidently say we have a bead on what the audience expects from us and, whereas we aspire to always exceed expectations, yes, there are times when we have to make hard decisions in order to operate within budget. In all honesty, compromise is not one of our strong suits. Infinity tends to stretch the natural limitations of a new theatre company to the point of ridiculousness.

What has been the most rewarding production to date of Infinity for you (artistically speaking)?

Wow, which child to favor? If we had to pick, we’d say Dames at Sea. This 2012 production was a perfect vehicle for a world-renowned artist—Randy Skinner, the Director/Choreographer of the show. The dancing in the show was truly amazing with an unparalleled level of tap dance. But moreover, Randy was able to deliver a production that went seamlessly between satire of and homage to the great movie musicals on which it’s based.

What has been the most ambitious production and why?

2013’s She Loves Me, for sheer size of production. Whereas it’s considered a small show, for us, it was our biggest, at fourteen people in the cast, and six live instrumentalists. Also, we built a moving set including a scene in which a gorgeous Austrian curtain was dropped from the fly system in the theatre. It was worth it. We gained so much by producing this show, and the audience definitely absorbed the exquisiteness of that script and score.

Does the Annapolis/Anne Arundel community have the depth of talent needed for high quality productions or do you find yourselves “coaching up” the talent to fit the bill?

Annapolis is a town with a rich tradition of community theatre, and is now an emerging professional theatre town. When we have engaged local talent, we do it because they are ready to perform at the high standards that we set. We do take on the responsibility of helping young artists grow, with our internship program and master classes. This is a great opportunity for college students about to join the professional world and teenagers considering a career in theatre.

What impresses you the most about the local performing arts scene?

It’s gumption. Annapolis can be a tough place to draw an audience for theatre, and an even tougher place to get the attention of the benefactors of the community. But theatre, concerts, operas, and dance pieces are constantly happening that show people the joy of the live interaction that you don’t get in front of a TV or computer.

Outside of Infinity Theatre, you involved in a number of endeavors/orgs, both local and remote; what are a few of them and is there an underpinning philosophy you have about giving back and/or engaging the community/arts scene?

Part of the proceeds of Infinity shows are donated to the Children’s Theatre of Annapolis, a wonderful, historic non-profit. CTA counts Anna as an alumnus, and provides Infinity with a lovely venue. Secondly, Anna is the Founder and Executive Director of Arts for All, and Alan is on the board, which gives artistic opportunities to disadvantaged kids in NYC. I would say that the underpinning philosophy is that the world needs more accessible opportunity for live performance and all the arts.

Do you have a particular production in mind that you consider the “holy grail” and that you’d like to produce with Infinity Theatre?

Our grail is not a singular production, but rather a full season of productions—not just in the summer—in which we have actively engaged Annapolis in full support of our adventure. That said, we can’t wait to get the rights to produce Jersey Boys.
For tickets and more information, visit or call 877-501-8499.