After graduating from Samuel J. Tilden High School he served in the United States Army from 1942 to 1946 with the 594th Engineer Boat and Shore Regiment, stationed in the Philippines, New Guinea and Japan.

Appreciating Macy's comedic skills off Broadway, Norman Lear brought him to Hollywood, where he first got a small part as a police officer in All in the Family.

He was cast in the role of Walter Findlay, the husband of the title character on the 1970s television sitcom Maude, starring Bea Arthur.

[9] Macy appeared in the television movie Perry Mason: The Case of the Murdered Madam (1987) as banker Richard Wilson.

[3] Macy appeared as the jury foreman in The Producers in 1967, with the memorable sole line "We find the defendants incredibly guilty".

Other memorable roles include the co-inventor of the "Opti-Grab" in the 1979 Steve Martin comedy The Jerk and as the head television writer in My Favourite Year (1982).

Other film credits included roles in Death at Love House (1976), The Late Show (1977), Serial (1980), Movers & Shakers (1985), Bad Medicine (1985), Tales from the Darkside (1985 - "Lifebomb" episode), Sibling Rivalry (1990), The Doctor (1991), Me Myself & I (1992), Analyze This (1999), Surviving Christmas (2004), The Holiday (2006), and Mr. Woodcock (2007).