Robert Dutton

Robert Dutton (“Bob”), a writer, teacher, producer, actor, theater and film buff, and a friend to many, passed away in his home on August 27, 2020, surrounded by family, including his beloved dog Pika. He was taken by glioblastoma, an aggressive brain tumor.

–Mark Lovewell, Vineyard Gazette

Bob was born on Oct. 18, 1961, in Poughkeepsie, N.Y. He was the last of four sons born to David Garland Dutton and Barbara McDowell Dutton. The family, including brothers David, Allan, and John, spent summers in Harthaven in Oak Bluffs during Bob’s childhood. In 1976, when Bob was in 10h grade, the family moved to the island year-round.

Bob found his calling in the theater department at MVRHS, and after school in many ITW productions. It was a joyful next step to Emerson College, where he graduated in 1983 with a B.F.A. in theater directing. Here his special passion for musicals flourished while he made lifelong friends in shows and Phi Alpha Tau.

After a brief stint in Los Angeles working for Taft/Barish Productions, he returned to the Island and opened the iconic Island Entertainment video store. Due to his friendly nature and knowledgeable staff, IE became the place to discover great films and enjoy movie banter. Bob simultaneously pursued more musical theater directing projects and acting roles with ITW and the M.V. Playhouse, and became a member of Actors’ Equity Association in 1989.

After four years of store ownership, Bob’s passion for new creative projects led to selling Island Entertainment (which continued for decades under the skilled leadership of dear friends) and moving to Orlando, Fla., with his future wife and fellow professional performer, Molly Conole. They were married in 1993 at the M.V. Playhouse, aptly in a costume-themed wedding.

Bob worked as an actor at Universal Studios and Disney, and considered these times with talented friends a pinnacle in his life. As friend and fellow performer Greg Triggs said, “He always arrived with a contagious joy.” He brought that youthful enthusiasm to many projects that he engaged in during these times — publishing Classic TV Magazine, opening the Film Society video store in Orlando, and working as a marketing director for SAK Theatre and the Starlight Dinner Theaters. He also began his playwriting through two productions at the Orlando International Fringe Festival, capturing his wit and humor: “Out of the Woods (and Into the Frying Pan)” and “The Weekly Actor of the Year Competition.”

The other huge joy in Bob’s life was being a father to his two children: Amelia Belle Conole Dutton (born 1994) and Simon Pierre Conole Dutton (born 1998). His kids brought out the impish kid as well as the kind teacher in him, leading naturally to his next passion. He taught English and drama for middle and high schoolers at Central Florida schools for 13 years. His classes, like his life, were full of creativity and not textbook-based. He pushed his students to think outside of the box, to be creative, honest in writing and acting, and to work hard. He was voted “Best Teacher in the Orlando Area” by Orlando Home & Leisure Magazine in 2011.

In 2013, Bob and family moved back to the Vineyard. Bob taught drama briefly at MVRHS, then found a way to incorporate his love of film and teaching at the M.V. Film Society. Bob was theater manager there, recognized as a friendly greeter of patrons. He provided informative introductions to films, and also taught many film classes to deepen appreciation for dramatic techniques and structure. Episodes of his series “Film Talk,” which have had thousands of views, can be found on the M.V. Film Society’s website under “Education.”

Bob continued his passion for writing in most recent days by working on many projects. His “Office Noise” farce was awarded top prize in the Kaplan New Playwrights/New Plays Competition by the Eventide Theatre Company in 2018. His full-length musical “The Ivory Door” received the precious gift of a staged reading by dear friends via Zoom. Bob was able to hear his words, and many themes that were important to him, come to life. He was also writing scripts for a TV series about a bisexual male in the title role of “Tom.”

Bob made the courageous decision to come out as bisexual on his 55th birthday. He was active as a mentor in MVRHS’s Gay-Straight Alliance, and was working on starting a PFLAG organization on the island. He considered open-mindedness and love the highest values. His work will be continued by others.

Bob was the embodiment of these words of wisdom from his own “The Ivory Door”: Live well the life you have been given.” That he did, with glee.

Bob is survived by his wife Margaret A. (“Molly”) Conole, daughter Amelia, son Simon, and dog Pika. He was predeceased by his father, David G. Dutton, in February of 2020, but survived by his mother, Barbara Dutton, of Harthaven, his brothers David M. (wife Renée), Allan (wife Bianca) and John; and by his nieces and nephews Stanley, Chloe, and Allan Lourdan.

A celebration of his life, aptly titled “Honoring Bob In Costume” will be held via Zoom on Sunday, Sept. 6, at 2 pm. Attendees are encouraged to dress in any creative way that brings them joy and to log in early. A link to his service is here:

Bob would appreciate donations in his name to any of these worthy organizations:, Bisexual Resource Center (, M.V. Film Society, M.V. Playhouse, or Hospice of M.V.