Milman attended Northwestern University, then received his Master of Fine Arts in acting at the Yale School of Drama.

Milman began his career as a playwright; his first play, "A Visionary Drowns", which he had written while a student at Northwestern, premiered in New York, Off-Broadway, when he was 22.

Milman's television credits include roles on The Sopranos, Law & Order: Criminal Intent, and the short-lived Love Monkey.

In the spring of 2009, Milman was cast in the pilot episode of The Wonderful Maladys for HBO, starring Sarah Michelle Gellar.

In late 2016 it was announced[3] Derek's debut Young Adult novel, Scream All Night, would be published by Balzer + Bray, an imprint of HarperCollins.