In 1952, at the age of fifteen, Gail became a member of the Les Grandes Ballets Canadiennes. At the age of 26, she later posed in a tight-fitting sweater for Playboy Magazine, as one of "The Girls from Canada" on November 1963. She later taught ballet in the Berkshires from 1973 - 1995.
During her dancing career, Gail started her acting career in 1964 when she played in four television series, Mr. Nova, My Three Sons, Perry Mason, and Wagon Train (all based in 1964).
Between 1964 and 1965, Gilmore appeared in six movies leaving an indelible impression on fans of teenage drive-in movies. Gilmore co-starred with Elvis Presley twice, playing a vacationing coed in Girl Happy (1965) and a dancing gypsy in Harum Scarum (1965). She then frolicked on the seashores of sunny Southern California in The Girls on the Beach (1965) and Beach Ball (1965) before growing to gigantic proportions along with five other delinquent teenagers who terrorize a town named Hainesville, California, in Village of the Giants (1965). After finishing the set of The Loved One (1965), Gilmore met writer, Terry Southern, and left Hollywood in 1966 where she lives with him in New York then Connecticut where she remained his longtime companion until his death thirty years later.
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