Masterson's performance career began as a dancer which she gave up at age 11 after being cast in The New Adventures of Pippi Longstocking.[1] Masterson started her acting career as a child actress at age 14 with her first appearance as Head Girl in "The New Adventures of Pippi Longstocking", a fantasy-adventure, musical, family film based on the books by the late Astrid Lindgren. Fay originally auditioned for the role of Pippi Longstocking, but the role went to her former co-star Tami Erin. Ken Annakin liked her so much that he wrote the part of the head girl at the children's home just for her.[2]
Since then she has appeared in over twenty-five films and over thirty-five television productions.[3] She has additionally voiced characters in several video games.[3]
In 1986 she was interviewed by a stand-in presenter Kenneth Williams on the British tv show Wogan.[4]