Jonathan Lipsky, the playwright, director, writer, professor and beloved Island figure known for his generosity of spirit and fierce intellect, died on Saturday, March 19 at his home in West Tisbury. He was 66 years old. The cause was carcinoid, a rare type of cancer.

At his memorial service on Monday, held at the Hebrew Center in Vineyard Haven, Rabbi Brian Walt referred to Mr. Lipsky as a man “who loved music, words and silence.”
From this foundation sprang a seemingly endless fascination with and excitement not only for the arts but for life in all of its myriad complexities.

Mr. Lipsky was the author of numerous plays including, but not limited to, Maggie’s Riff, They All Want to Play Hamlet, Dreaming with an AIDS Patient, Living in Exile, and Walking the Volcano, which premiered in 2009 at the Vineyard Playhouse, where he was the associate artistic director for many years. He also collaborated with jazz musician Stan Strickland on Coming Up for Air, for which he won the 2007 Elliot Norton Award for directing.

Mr. Lipsky is perhaps best known for his work with dreams and how they can be harnessed to get at one’s emotional core. The emotional immediacy of his work, even those plays written decades ago, stemmed from his ability as an artist to plumb these depths. His book Dreaming Together: Explore Your Dreams by Acting Them Out is the seminal source for this technique.

Dr. Gerry Yukevich, a friend and actor who performed in Mr. Lipsky’s play Dreaming with an AIDS Patient, which was created using Mr. Lipsky’s dream method, remarked on the experience in a 2008 Gazette article. He wrote that after each performance, “the audience sat in a tearful, meditative trance. Each time the audience walked out in a silent, deeply reverential daze.”

Jonathan Lipsky was born in 1944, the second of three boys, in New York city. His mother, Hannah Kohn Lipsky, was a psychiatric social worker and his father, Eleazer Lipsky, was an attorney and novelist. His grandfathers were prominent Jewish leaders; Louis Lipsky was a cofounder and once the president of the Zionist Organization of America and Jacob Kohn was a conservative rabbi who founded the University of Judaism in Los Angeles.


Kanta Jonathan
Kanta and Jon Lipsky.

Jon attended Bronx High School of Science in New York city, Oberlin College and the Iowa Writers’ Workshop. He also spent two years in India as a member of the Peace Corps.


In the 1970s, Mr. Lipsky became the in-house dramatist for Theater Works in Boston, which presented many of his early plays. Paula Langton, who now heads the acting program at Boston University, remembered those days in an interview with the Vineyard Gazette, published earlier this year. “He was among the theatre gods when I was in school,” she said. “One of those really cool people who did amazing theatre.”

Over the years Ms. Langton acted in a number of Mr. Lipsky’s plays and also taught a class with him at Boston University, where Mr. Lipsky was a professor of acting and playwrighting for almost 30 years. “He has [students] write up contracts for themselves about ways they want to challenge themselves as performers and as people to grow,” Ms. Langton said, about a class they taught together for incoming freshmen called Locals. “He just signs the contract. He doesn’t grade it or judge it. He has this brilliant way of being a witness for them and bearing witness to their process and giving them free rein to see how far they want to go. It’s such a gift.”

Brooke Hardman and Brian Ditchfield, two of his former students, who are now married to each other and living on Martha’s Vineyard, first met in Mr. Lipsky’s classroom. Reflecting back on the experience of being Mr. Lipsky’s students, they remembered him as “gentle and understanding of freshman-year dramas. He listened. He advised. He was certainly a father figure to us all in that first year. His primary task was freeing you to explore your impulses, citing that if you can’t understand your own feelings, your own self, how will you ever truthfully convey the feelings of a character? It was often said that he taught Feelings 101.” Ms. Hardman and Mr. Ditchfield remained colleagues and friends with Mr. Lipsky throughout his life.

Mr. Lipsky began visiting Martha’s Vineyard as a child during summers and later, in 1984, married his second wife, Karen Shigley, who now uses the name Kanta, at a ceremony at the Lambert’s Cove Methodist Church.

His first marriage to Jeanne Baker ended in divorce. They remained close, however: “Although we ceased to be married to one another more than three and half decades ago, he has remained a dear friend to this day,” Ms. Baker wrote in a note after his death. “Thank you, Jon, for being my lifelong beacon of hope and comfort.”

Jon and Kanta moved to the Island full-time in 1996 with their two sons, Adam and Jonah. He continued to teach at Boston University, work as a playwright and director for the Boston History Collaborative and as a playwright and artist-in-residence at the Museum of Science in Boston. A man of indomitable energy and drive, Mr. Lipsky continued to write plays while struggling with cancer.

Walking the Volcano, which began as a series of short plays submitted to the Boston Short Play Marathon, had its premiere at the Vineyard Playhouse in July of 2009. The play was directed by MJ Bruder Munafo, the artistic director of the Vineyard Playhouse.

Since 1996, four of Mr. Lipsky’s plays were performed at the playhouse. He also directed another eight plays there, initiated the college intern program, established staged readings during the summer which evolved into the present Monday Night Specials, codirected for two years the Vineyard Summer Actors Institute, and served as associate artistic director, artistic associate and on the board of directors.

“Jon Lipsky was a fiercely enthusiastic theatre artist, particularly when it came to his own work and the work of those he knew and admired,” Ms. Bruder Munafo said. “He was an important figure at the Vineyard Playhouse for over 15 years and contributed greatly to the life of the theatre. The plays he wrote are stunning and sincere; he exposed the hearts and guts of his characters and demanded brutal honesty, using raw words and brilliant imagery. I shall miss Jon greatly, his unique take on things, his towering spirit and his passionate pursuit of his dreams.”

Mr. Lipsky was a familiar figure all over the Island, usually wearing his beret and not getting anywhere quickly because so many friends eagerly engaged him in conversation at every turn. Island historian Linsey Lee remembered Jon as both a friend and an inspiration. “Jon so loved the Vineyard, the sparkling light on the ocean, the flowering of spring and his asparagus emerging in his garden … but most of all he loved the people and the sense of community here. He had an insatiable curiosity for what makes people tick, how they learn, how they love, how they dream, how they work together.”

Arnie Reisman, a longtime friend who first hired a young Jon Lipsky to write articles for Boston After Dark, concurred. “He had an infectious spirit. He had an infectious generosity. He had an infectious laugh. The man was a walking germ, spreading kindness and good humor wherever he went.”

During the past year as Mr. Lipsky struggled with his illness, many on the Island rallied to help. In January the very first play he wrote, Beginner’s Luck, was performed at the Hebrew Center in a tribute to his legacy. Mr. Lipsky attended the performance as colleagues and former students brought this early work of his to life yet again. One of the actors was Ms. Langton.


Of the experience of continuing to work with Mr. Lipsky during his protracted illness, Ms. Langton said, “One of the things that Jon has said to me, when I get really close-up and eye-to-eye with him — and he’s amazing, because you can really talk to him about mortality and what it’s like to be sick — he looked at me way up close and he said, ‘I feel loved. I feel so loved.’”

Mr. Lipsky is survived by his wife, Kanta, sons Adam and Jonah, and two brothers, Michael and David.

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