- During high school, Sky performed multiple character roles in an original radio drama version of "Lord of The Flies" broadcast on Boston's WBZ radio.
- In the early days, to help pay the bills, Sky spent a number of years as an on-air talent in the radio broadcasting business, during which he interviewed such luminaries as Red Skelton, Harry Belafonte, Alice Cooper, Jay Leno and many others.
- Some unique early professional (paid) acting jobs for Sky included: an educational movie about the importance of physical fitness for children, which was produced by Encyclopedia Britannica Films (Sky was nine years old at the time and this was his first paid acting job). Ten years later, Sky donned the giant cheeseburger-headed costume of McDonald's character, "Mayor McCheese", for an appearance on Boston TV's local version of "Romper Room" (Sky was 19 at the time and attending Emerson College).
- Sky has experienced (and survived!) a tandem skydive out of an airplane at 12,000-feet.
- Sky once performed the role of "Sky Masterson" at his Cambridge, Massachusetts high school. The name "Sky" stuck as a nickname that has stayed with him throughout his career. Also starring in the young cast were future TV, film and stage star, Jere Burns, future Shakespearean actor, Jonathan Epstein, and Alexander (Sandy) Wells, who is a critically acclaimed L.A. actor and former News Anchor at KABC radio in Los Angeles.
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