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He earned his first feature screenplay credit with Framed (1947). Other screenplays include Clarence Brown's Intruder in the Dust (1949, an adaptation of the William Faulkner novel), John Huston's The Asphalt Jungle (1950, for which he received an Academy Award nomination), Johnny Guitar (1954, credited to Philip Yordan, God's Little Acre (1958, an adaptation of the Erskine Caldwell novel officially credited to Philip Yordan as a HUAC-era "front" for Maddow), and, again with Huston, an Edgar Award for Best Mystery Screenplay) and The Unforgiven (1960).

As a documentarian he directed and wrote such films as Storm of Strangers, The Stairs, and The Savage Eye (1959), which won the BAFTA Flaherty Documentary Award. Maddow made his solo feature directorial debut with the striking, offbeat feature An Affair of the Skin (1963), a well-acted story of several loves and friendships gone sour and marked by the rich characterisations which had distinguished his best screenplays.

In 1961, Maddow and Huston co-wrote the episode "The Professor" of the 1961 television series The Asphalt Jungle. In 1968 he wrote a screenplay based on Edmund Naughton's novel McCabe; while a film adaptation of the novel was ultimately produced as McCabe & Mrs. Miller (1971), Maddow wasn't credited on the film. His final screenplay was for the horror melodrama The Mephisto Waltz (1970).