Trained in acting by William Hickey. Worked with Julian Beck in The Living Theater, one of the leaders in avant-garde theater during the 1960s in New York.
Once taught English at a private school in New York called Oakland Academy.
Received a Dramalogue Award and L.A. Drama Critics Award for writing and starring in "Once In Doubt" at the Los Angeles Theatre Centre.
Received the 1997 Dramalogue Award for his performance in the play "Buried Child".
Barry earned a degree in philosophy at Brown University before being accepted by the Yale University School of Drama.
Worked first as an artist in New York City before becoming a professional actor. He still paints and sculpts, and has examples of his artwork on his website, raymondjbarry.org.
He was a football player at Brown University. During his junior year, a theater professor approached him about portraying Hal in a production of William Inge's "Picnic," saying they were interested in getting a football player to portray him. He declined several times before giving in.
As of 2018, he has appeared in three films that were nominated for the Best Picture Oscar: The Goodbye Girl (1977), An Unmarried Woman (1978) and Born on the Fourth of July (1989).