He is the writer of the off-Broadway play The Caterers,[1] which was nominated for Best Full-Length Original Script of 2005-2006 in the Innovative Theater Awards.
In June 2006, he was featured in Time Out New York magazine in an article on America's most important young playwrights and compared to Nobel Prize-winning author Saul Bellow for his "literacy and seriousness".
Praised by The New Yorker, The Wall Street Journal and Broadwayworld.com, among others, the play ran in January 2007 at the Upper West Side's Arclight Theater.
In 2009, Leaf published his first full-length nonfiction book, The Politically Incorrect Guide to the Sixties, in which he attacks popular perceptions of the 1960s as a radical decade dominated by hippies, rock music and free love.
Entitled City of Angles, it received uniformly enthusiastic reviews with Kirkus saying that it was 'light, literary entertainment at its best—easily companionable, intelligent, and brimming with artful humor.