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George Jocelyn, an early addition to and long-time mainstay of the Stratford Festival’s music program served as a minder for many storied jazz artists, including Billie Holiday.Peter Smith

Endlessly curious, with protean talents and a great back story, Gordon Jocelyn lived a life steeped in culture, one in which he reinvented himself as needed and never shrank from a challenge or opportunity. Or great personal grief.

A musician, teacher, reluctant soldier, feminist, actor, television host and a resilient soul, Mr. Jocelyn saw all four of his children become artists. Apart from inspiring alternative ways of thinking, he peppered them with one question: "Why?" Why go to university instead of travel? Why this book and not another? Why conform?

"He did that every day of our lives," recalled his son Matthew Jocelyn, artistic and general director of the Canadian Stage theatre company in Toronto. But it was never in a judgmental way. To him, "there was no such thing as a mould to which one should subscribe."

An impish man never at a loss for a quip, he instilled independent thought and action in his family and students but had an unquestioning sense of right and wrong. "Sure, he wanted us to be free thinkers," said his children in a family death notice, "but we damn well better speak good English and distinguish between 'may' and 'can.'" It was a discipline passed to his two granddaughters, who know the difference between sarcasm and irony, "and use both to wicked effect."

Mr. Jocelyn, who died in Toronto on Nov. 28 at the age of 96, was an early presence at the Stratford Festival's music program, where he was a minder for the jazz great Billie Holiday and other notables. His work at the festival was fitting, as Stratford, Ont., is where Arthur Gordon Jocelyn was born, on May 26, 1920.

The story of his parents was compelling. His father, Arthur, was abandoned as a baby and raised at the Foundling Hospital in London, England, founded in 1739. The novelist Charles Dickens lived nearby and used to visit the children there on Sundays while he was writing Oliver Twist. The composer George Handel had been one of the institution's early supporters, so music was taught rigorously. The senior Mr. Jocelyn became an accomplished clarinetist.

Gordon Jocelyn's mother, Annie Bennett, was also an orphan, raised in a London orphanage. She met her husband-to-be at a dance, but Arthur decamped for Saskatchewan to farm, lured by an ad for Canadian homesteaders. He tried but failed in his bid to become a farmer. He then heard that the Grand Trunk Railway needed workers in Stratford. He sent for his bride and the couple settled in the Ontario town, their lives interrupted by war back home: Arthur served as a medic and musician during the Boer conflict in southern Africa, and again during the First World War as a massage therapist stationed in England for war-weary soldiers returning from battle.

His son, Gordon, meanwhile, had become a piano prodigy and by the age of eight was performing publicly at local churches and clubs. The town of Stratford later raised money to send him to the Royal Academy of Music in London. He and his teacher were en route to New York on Sept. 3, 1939, to catch the boat when they heard King George's speech announcing war with Germany. The scholarship was transferred to the Eastman School of Music in Rochester, N.Y., where he spent a year before joining the Royal Canadian Air Force (it had "snazzier" uniforms than the army). He was stationed in Saskatchewan, got married on leave in October, 1942, to Joy Martyn, who had "the best gams at Central High," and left for England in 1943 as a gunnery instructor stationed in Yorkshire.

"He knew nothing about gunnery," said his daughter, Marthe, a children's book author who has also designed clothing and toys. "But he had been a teacher [of piano] so they put him a position of teaching."

Mr. Jocelyn was an avowed pacifist and his family believes he regretted not having declared himself a conscientious objector (he thought that joining as an officer rather than being conscripted would keep him from seeing action). "He never spoke about it," said his son, Matthew. Added his daughter, Marthe: "He recognized the valour of those who fought but he really didn't want anything to do with it."

Back home at war's end, he earned a bachelor's degree in music from the University of Toronto, but deciding he wasn't good enough to become a concert pianist, completed a master's degree in English literature, with a specialty in the poet T.S. Eliot.

"He developed a profound passion for literature," Matthew said. "He really found himself in that world."

Among the original crew at the Stratford Festival in the early 1950s, he was a dresser for the British actors James Mason and Alec Guinness, with whom he remained friends. He went on to become assistant to the festival's director of music, Louis Applebaum, and in 1957, became the music administrator, importing such talents as Ms. Holiday, the conductor Benjamin Britten, jazz great Dave Brubeck and French mime Marcel Marceau, who came to take part in Igor Stravinsky's L'Histoire du soldat.

He began a long stint teaching English at Toronto high schools, but at the age of 50, took a year-long sabbatical and travelled through Europe with his wife. After taking stock, he returned for a job at Toronto's alternative high school, SEED, North America's oldest public alternative secondary school. He loved it and was in his element in a place that drew clever misfits – "a reflection of who he was as an 18-year-old," said his son. He taught there for five years, provoking his students to think for themselves and chart their own course.

He went to bat for underachievers as well. Marc Mayer flunked out of high school, yet Mr. Jocelyn wrote a letter of recommendation for him to attend university as a mature student. "Gordon's letter convinced the university that I was worth a try, but it stunned me," recalled Mr. Mayer, who had been romantically involved with Mr. Jocelyn's son Tim. "Beautifully crafted, it made the most emphatic case for my merits and I was overwhelmed with gratitude. …

"I went on to do well in school and to have a far more interesting career than I could have ever imagined. Gordon Jocelyn changed my life and I believe that there are quite a few of us out there who could say as much about him," said Mr. Mayer, now director of the National Gallery of Canada.

After the death of his wife from cancer in 1976, Mr. Jocelyn won a job co-hosting CBC Television's From Now On, a noon-hour program geared to those over 55. It was co-hosted by the journalist Lotta Dempsey and aired in 20 cities. He loved it, his children say, partly because it afforded him the opportunity to buy new clothes and dabble in a new art, cooking.

Not done yet, he became a full-time actor on stage and TV in his 60s, appearing in plays by Shakespeare and David French. The Internet Movie Database lists two dozen acting credits, including roles in the television shows Anne of Green Gables, Street Legal and Wind at My Back, and movies such as The Dead Zone with Christopher Walken.

He also learned to knit, making elaborate jackets and blankets. Later, he did needlepoint, freehand. "He was very flexible in his understanding of gender," said Matthew, "and would say as much."

He "was probably the first pro-feminist man I ever knew," said former Olympian Bruce Kidd, who was a student in Mr. Jocelyn's Grade 12 English class at Toronto's Malvern Collegiate Institute and is now vice-president and principal of the University of Toronto's Scarborough campus.

"He was always talking about a man's responsibility, especially around the household, and calling us on stock criticisms of women."

His lessons on relations between the sexes were also steamy, at times. He "could turn a poem about autumn into something erotic and he made it clear that he was talking about his wife," Mr. Kidd recalled. "The whole class would emerge blushing." Mr. Kidd stayed in touch with his teacher after graduating. "I always loved his spirit and his stories."

Mr. Jocelyn had his own annus horribilis, enduring what no parent should – times two. In 1986, his son, Tim, a talented artist and free spirit who once lived in a cave in Nepal, died of complications from AIDS. Mr. Jocelyn's response was to join the bereavement team at Toronto's Casey House Hospice, where he read aloud to patients for years after.

Also in 1986, his daughter Paula, once a dancer and aspiring translator, died after getting struck by a taxi in Toronto; nine years earlier, she had been hit by a car in France and left brain damaged and a paraplegic.

Marthe doesn't know how her father coped. Being stoic was part of it. He hopped a freighter to Europe and was gone for several months, visiting friends he'd made during the war. "When he got back, I moved home to be with him," she said.

"I taught him to cook and we slowly dispersed belongings. He got a couple of small parts in amateur theatre. He freed himself of fetters and loosened his grip on memories so that he could move forward and become a new man."

He leaves his son, daughter and two granddaughters.

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