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Castellaneta was born in Oak Park, Illinois, a suburb of Chicago, on October 29, 1957, to Elsie and Louis Castellaneta.
His father was an amateur actor who worked for a printing company.
Castellaneta became adept at impressions at a young age and his mother enrolled him in an acting class when he was sixteen years old.
He would listen to his father's comedy records and do impressions of the artists.
He was a " devotee " of the works of many performers, including Alan Arkin and Barbara Harris and directors Mike Nichols and Elaine May.
He attended Oak Park and River Forest High School and upon graduation, started attending Northern Illinois University ( NIU ) in the fall of 1975.
He studied art education, with the goal of becoming an art teacher.
He became a student teacher and would entertain his students with his impressions.
Castellaneta was also a regular participant in The Ron Petke and His Dead Uncle Show, a radio show at NIU.
The show helped Castellaneta hone his skills as a voice-over actor.
He recalled " We did parodies and sketches, we would double up on ( characters ), so you learned to switch between voices.
I got my feet wet doing voiceover.
The show was just barely audible, but we didn't care.
It was the fact that we got a chance to do it and write our own material.
" He took a play-writing class and auditioned for an improvisational show.
A classmate first thought Castellaneta would " fall on his face with improvisation " but soon " was churning out material faster than could make it work.

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