William "Bill" James Chesterman

It is with profound sadness that we announce that William “Bill” James Chesterman, 77, of Calgary, passed away surrounded by family and friends on January 31, 2026, after a brief illness.

Bill was born on August 27, 1948, to Harold and Mabel Chesterman in Montreal, Quebec. The family moved to Calgary when Bill was 14 living in the Northwest part of the city. Bill really hit his stride in Calgary when he attended and then graduated from James Fowler High School. It was in high school where he began to get involved in the performing arts.

In 1968 Bill auditioned and was accepted as one of the original cast members of the Young Canadians of the Calgary Stampede. He performed on the Grandstand stage for five years as a Young Canadian and eventually another 7 years as a YC alumni. Bill loved his time as a member of the Young Canadians and built lifelong friendships with other cast members. Bill was so proud to represent Calgary and the Stampede when he performed not only on the grandstand stage but at fairs and exhibitions across Canada and the US. The Young Canadians became a steppingstone for Bill as he went on to perform as a regular member of the OK Corral, a singing and dance ensemble on the Tommy Hunter show, and later appeared in many movies and TV shows as an extra.

Bill enjoyed his time in show business but returned to Calgary, taking on a variety of jobs throughout the years. These included being a roofer, supporting worker’s rights as a Union Rep for both the Sheet Metal Workers Union and ACTRA, working for an oil well servicing company and eventually starting and running his own “Fire Pro” Business for 20 years servicing fire extinguishers and kitchen systems. Bill ultimately sold off his company and took some pre-retirement work that proved to be one of his most treasured jobs. He drove a school bus for 13 years and was affectionately known by the kids on the bus, as ‘Mr. C’. Bill always spoke highly of the kids he drove and continued to stay in touch with a few of his favorite students even after he decided to retire to spend his golden years focusing on his family and many friends.

On the family side of his life, Bill was a single dad for several years before he met Fran, the love of his life, in 1992. Together, Bill and Fran along with his son Chris, built a wonderful family life enjoying time together camping, visiting with family in BC, Ontario, and Arizona as well as taking many trips on his motorcycle. Bill’s life was full in so many ways, having the opportunity to do so many things that most people only dream of.

Bill would be the first person to tell you how blessed his life was to have so many friends and be surrounded by an amazing immediate and extended family who always loved unconditionally!

Bill was predeceased by his parents (Harold and Mabel Chesterman), brothers (Gerry, Robert), sister-in-law (Anna Marie Picone), and brother-in-law (Dan McFarland). Bill is survived by his life partner Fran Picone, son Chris, sister Joy (Murray), brother Milt (Ilene), sister-in-law Pat, sister-in-law Corinne McFarland (Picone), brother-in-law Carmin Picone (Fran) and brother-in-law Len Quiring as well as many loving aunts, nieces, nephews, cousins, and many friends.

We would like to thank the staff of the Peter Lougheed Hospital Unit 54 as well as the Dulcina Hospice staff for the amazing care they provided for Bill in the last couple of months of his life. A special thanks also to Fran’s Auntie Gina for her support for the last several weeks. As per Bill’s request, a celebration of his life will be held at a later date. In lieu of flowers, the family requests donations be made to the Kidney Foundation or a charity of your choice.

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