Chester was born in West Covina, California, the son of Cecil, lead singer in the rock band “Whiskey”, and Linda, a homemaker.
Following graduation, he performed in various stage productions in New York, including a play written by Joanne Woodward who, upon noticing his naturalistic acting style, encouraged Chester to pursue a career in film.
In 2009, Showtime optioned the book with Chester set to adapt it into a television pilot with Don Roos, Dan Bucatinsky and Lisa Kudrow as producers.
Writing for The Village Voice, Melissa Levine described writer-director Chester's debut as “truly enjoyable”,[12] while Ronnie Scheib of Variety praised his performance: “Chester’s Adam, effortlessly able to slide from bathos to pathos and back again with none of the smarmy schmaltz of sitcom humanism, is a marvel of nuanced comic timing.”[13] Chuck Wilson, writing for LA Weekly described the film as “something certain to make John Waters cackle with glee.”[14] Adam & Steve has since developed a cult following.
[15] On the June 5, 2013 edition of NPR's “Moth Radio Hour”, Chester recounted how he has been haunted by the Academy Award-nominated actor, Montgomery Clift, who has been dead for over 40 years.