As a child, Cantone would direct reenactments of shows. Cantone's first impression was of Julia Child, which he presented in a junior high school talent show. He graduated from Stoneham High School in 1978 and Emerson College in 1982. He befriended fellow comic Denis Leary at Emerson. He moved to New York City in 1983 and got a job as a chocolate vendor at Trump Tower.
While working at Trump Tower, he did impressions of people while selling chocolate truffles. He later worked as a jewelry salesman, quitting a year later to pursue comedy full time. He began his professional career hosting a children's show called Steampipe Alley, which aired on New York-New Jersey superstation WWOR-TV from 1988 to 1993.
In October 2011, Cantone married his partner of 20 years, musical theater director Jerry Dixon. The ceremony was officiated by pastor Jay Bakker.
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