His first play to be staged in New York City was When You Comin' Back, Red Ryder?, which won him the 1974 Drama Desk and Obie Awards for Outstanding New Playwright.
Medoff's big breakthrough and most famous work was 1979's Children of a Lesser God, which won him the Tony, Drama Desk, and Laurence Olivier Awards for Best Play.
Medoff's screen credits include adaptations of his plays Red Ryder and Children of a Lesser God, for which he was nominated for an Oscar, BAFTA, and Writers Guild of America Award, Clara's Heart (for which he cast, and subsequently "discovered", Neil Patrick Harris), and City of Joy.
[9] Medoff's theatre directing credits include Waiting for Godot, The Effect of Gamma Rays on Man-in-the-Moon Marigolds, Jacques Brel is Alive and Well and Living in Paris, One Flew Over the Cuckoo's Nest, Equus, and Hot L Baltimore.
As an actor, he has appeared in the plays Marat/Sade, Black Comedy/White Lies, and Old Times, among others, and the films The Twilight of the Golds, Santa Fe, Homage, Red Ryder, and Clara's Heart.