Pinsent, the youngest of six children, was born in Grand Falls, Newfoundland (present-day Newfoundland and Labrador, Canada). His mother, Florence "Flossie" (née Cooper), was originally from Clifton, Newfoundland and his father, Stephen Arthur Pinsent, was a paper mill worker and cobbler originally from Dildo, Newfoundland. His mother was "quiet spoken" and a religious Anglican; the family was descended from immigrants from Kent and Devon in England. He was a self-described "awkward child" who suffered from rickets.
Pinsent began acting on stage in the 1940s at the age of 17. He soon took on roles in radio drama on the CBC, and later moved into television and film as well. In the early 1950s, he took a break from acting and joined the Canadian Army, serving for approximately four years as a private in The Royal Canadian Regiment.
Pinsent's professional acting career began in 1957 at Winnipeg's Theatre 77 (later known as the Royal Manitoba Theatre Centre) under the direction of John Hirsch. In the years that followed, he performed in many theatrical productions in Winnipeg, Toronto and at the Stratford Festival.

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