Prairie Rose Cremation & Funeral Services

In Memory

Philip Headley

April 6th, 1941 - June 10th, 2024
Born in Barbados
Passed in Calgary, Alberta
Philip Headley

Philip George Alfred Headley, resident of Calgary Alberta, passed away on Monday June 10, 2024 at the age of 83 years old. He will be lovingly remembered by his sisters Violet Mootoo, Cynthia Holder, his brothers Hulbert Headley, Noel Headley, John Headley and many nieces and nephews. He was predeceased by his mother Claudia Headley, father Easton Headley, sisters Enid Searles, Dorothy Headley and his brothers Sam Headley and Edward Headley.

Phillip was born on April 6, 1941 to Easton and Claudia Headley in Bridgetown, Barbados. His lifes journey would take him from Barbados as a Lodge School graduate to Canada where he graduated from the University of Toronto. From there, Philip went on to become a High School teacher in the small town of Wawa Ontario and later finished his educational career in Saskatoon, Saskathewan where he would reside for the majority of his adult life. For over a 35 year span, Philip was a well respected University Professor and High School teacher. He was often referred to as this larger than life figure who taught Drama and Latin and brought people together.

In his free time Philip would enjoy several hobbies including playing chess, cribbage and dominos. He loved opera music, drama and theatre. In terms of sports he loved wrestling, he loved playing and wathcing tennis as much as possible. Most noteble, Philip had a strong and devoted love for his dogs. This love and relationship would span over 40 years. From Basset to Shaka to Cabra to Porscha, Philip shared a unique bond with each and every one of his pets. He loved going for walks with them frequently!

Our family would like to extend a special thank you to all the staff at AgeCare Skypointe who fondly called Philip 'The Professor' and took care of him over the past 6 years.

Share a message or memory
William Borland
1 month ago
I cannot explain the sudden urge to look up Mr. Headley at 4 am one morning, 51 years after we’d have last been together in Wawa Ontario. I’m certain he wasn’t cosmically reaching out to me, one of probably thousands of students encountered in his long career. I was moved to learn only now of his passing 10 months ago. As a retired teacher myself, I know first hand how the student names and faces blur over time. And yet, my hunch is he actually would remember me, and perhaps break out into a line of song from one of many high school plays he directed. That’s how I’ll choose to remember him. I’ve no doubt, however, that my memories of him would be stronger than his of me. As both the obituary and Bryan (hello old friend) point out, he was certainly bigger than life. Warm remembrances of countless drama and choir practices, backstage antics, road trips… Mr. Headley surely must’ve played a formative part in the lives of many. My sincere belated condolences to his family. I too wish simply to say, Thanks Mr. Headley.
Bryan Phillips
11 months ago
To Mr. Headley's family my deepest condolences. He really was bigger than life and made my life richer through his example. Thank you Mr. Headley.