DeForest grew up in Bay Ridge, Brooklyn. He was born to Calvert Martin DeForest, M.D., a physician who died in 1949, and Mabelle (Taylor) DeForest. His father was a cousin of radio pioneer Lee de Forest.
DeForest attended Poly Prep Country Day School in Brooklyn, New York. He was employed for many years as a file clerk at the pharmaceutical company Parke-Davis, which was later acquired by Pfizer. He had aspirations of acting but was discouraged by his mother, who was briefly an actress herself. After her death in 1969, DeForest did part-time backstage work, which eventually led to acting work, and is credited with appearing in five films from 1972 to 1982. He worked part-time as a receptionist at a drug rehabilitation center until February 1984, when his supervisor learned of his employment with NBC and his resulting ineligibility for the position (as it was part of a program designed for those who made under $6,000 a year) and asked him to resign.
In early 1982, DeForest was hired to appear on the new show Late Night with David Letterman. His late-blossoming television career began with a New York University student film project called King of the Zs, by future Letterman writers Stephen Winer and Karl Tiedemann, who brought him along when they joined the Late Night writing staff. The Associated Press noted: "DeForest's gnomish face was the first to greet viewers when Letterman's NBC show debuted on February 1, 1982, offering a parody of the prologue to the Boris Karloff film Frankenstein. 'It was the greatest thing that had happened in my life,' he once said of his first Letterman appearance."

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