Barry's initial venture into acting was in a production of Tobacco Road on stage in New York in the late 1930s.
Played in the 1936 "Night Waitress. By the 1950s, Barry was a supporting actor instead of playing leads in westerns. Early in 1955, he appeared as the bandit Milt Sharp in an episode of the syndicated series, Stories of the Century, starring and narrated by Jim Davis.
During the height of his Red Ryder fame, he married B-movie Actress Peggy Stewart, they divorced on April 12, 1944.
In addition to acting, Barry was also a Writer, writing the stories upon which the films Red Light (1949) starring George Raft and Virginia Mayo, Train to Tombstone (1950), and Convict Stage (1965) were based, and co-writing the screenplay as well as directing and playing the leading role of Jesse James in Jesse James' Women (1954).
Barry played "Clete" in the 1956 western film Seven Men from Now, starring Randolph Scott. He guest starred as Tanner in the 1958 episode "Bullet Proof" of the ABC/Warner Brothers series Sugarfoot, starring Will Hutchins; he was cast as Arkansas in the 1959 Sugarfoot episode "The Return of the Canary Kid". Barry appeared four times in the ABC/WB western Colt .45. Barry was cast as black-clad gunfighter in a 1961 episode, "Last Stop: Oblivion", of the ABC/WB western series, Maverick with Jack Kelly and fellow guest star Buddy Ebsen.
Barry played supporting roles in dozens of television series, particularly westerns. He appeared eight times on the long-running NBC series, The Virginian, in the 1960s. He appeared in six episodes of Michael Landon's Little House on the Prairie as farmer Judd Larrabee, and appeared in all-star TV miniseries, such as Rich Man, Poor Man Book II and The Dream Merchants.
On January 13, 1965, Barry was cast in the final episode of the short-lived Mickey ABC sitcom starring Mickey Rooney. Barry was cast as a freeloading friend who had saved Mickey's life in World War II. In 1966, Barry played Confederate soldier "Lt. Farrow" in the Western film Alvarez Kelly. Barry played a supporting role in the 1968 film, Shalako, with Sean Connery.
On July 17, 1980, Barry shot himself in the head at his home, shortly after police had left the residence after investigating a domestic dispute. He was estranged from his second wife, Barbara at the time—with whom he had two daughters. He is interred at Forest Lawn Memorial Park in the Hollywood Hills of Los Angeles.
