- 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.
- Barry earned a degree in philosophy at Brown University before being accepted by the Yale University School of Drama.
- 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.
- 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.
- Received a Dramalogue Award and L.A. Drama Critics Award for writing and starring in "Once In Doubt" at the Los Angeles Theatre Centre.
- 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).
- Once taught English at a private school in New York called Oakland Academy.
- Received the 1997 Dramalogue Award for his performance in the play "Buried Child".
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