After graduating from the University of Virginia, Willingham moved to New York City, where he became associated with such literary giants as Truman Capote, Norman Mailer, and Gore Vidal.
Sam Spiegel proposed him as a writer for the screenplay of "The Bridge On The River Kwai", after making "The Strange One", which was Willingham's first screenwriting credit. However, a meeting with David Lean didn't go well and the job of writing the script went to others.
Graduated from high school from Darlington School, Rome, Georgia.