Robert (Bob) Dutton, a writer, teacher, producer, actor, theatre and film buff, and friend to many, died at home on August 27 surrounded by family, including his beloved dog Pika. The cause was glioblastoma, an aggressive brain tumor.

Born on Oct. 18, 1961 in Poughkeepsie, N.Y., Bob 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 10th grade, the family moved to the island year-round.

Bob found his calling in the theatre department at the regional high school and after school in many Island Theatre Workshop productions. It was a joyful next step to Emerson College, where he graduated in 1983 with a BFA in theatre directing. At college his special passion for musicals flourished while making 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, it became the place to discover great films and enjoy movie banter. Bob pursued more musical theatre directing projects and acting roles with ITW and the MV Playhouse, and became a member of Actors’ Equity Association in 1989.

After four years of store ownership, his passion for new creative projects led to selling Island Entertainment (which continued for decades under the skilled leadership of dear friends) and moved to Orlando, Fla., with his future wife and fellow professional performer, Molly Conole. They were married in 1993 at the Vineyard Playhouse.

Bob worked as an actor at Universal Studios and Disney and considered his time there with talented friends a pinnacle in his life. He brought his youthful enthusiasm to many projects, 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 playwriting.

The other huge joy in Bob’s life was being a father to his two children, Amelia Belle Conole Dutton and Simon Pierre Conole Dutton. 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 were full of creativity and not textbook-based. He pushed his students to think outside the box, be creative, honest in writing and acting, and to work hard. He was voted best teacher in the Orlando area by Orlando Home and Leisure Magazine in 2011.

In 2013, Bob and family moved back to the Vineyard. He taught drama briefly at the high school, then found a way to incorporate his love of film and teaching at the MV Film Society. As theatre manager, he was recognized as a friendly greeter of patrons. He provided informative introductions to films and also taught film classes. Episodes of his recorded series Film Talk can be found on the film society website.

He continued his passion for writing by working on many projects. Office Noise, a farce, was awarded 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. He was also writing scripts for a TV series about a bisexual male in the title role of Tom.

He made the courageous decision to come out as bisexual on his 55th birthday. He was active as a mentor in the high school 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.

He 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 2020, and is survived by his mother, Barbara Dutton of Harthaven; brothers David M. and his wife Renée, Allan and his wife Bianca, and John; two nieces and a nephew.

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

Donations can be made to, Bisexual Resource Center (, MV Film Society, MV Playhouse or Hospice of Martha’s Vineyard.