Barry started recording locally in the late 1950s, and released two singles on Jin Records around 1960. The second single, released in 1961, "I'm a Fool to Care" was picked up for national distribution by Smash Records (4). The record reached #15 on the U.S. Black Singles chart and in April 1961, it peaked at #24 on the Billboard Hot 100. It sold over one million copies by 1968, earning a belated gold disc. The song also charted in the UK Singles Chart at #49.
The next single, "Teardrops in My Heart", also charted, it reached #63 in Billboard in August 1961. Barry left Smash in the mid-1960s to record exclusively for Huey P. Meaux's Princess label. During this era Barry frequently played at Papa Joe's in New Orleans, and the Esquire ballroom in Houston. Disgruntled by loss of royalties through fraud, he very shortly gave up music around 1967. He returned soon after to record for Houma, the label he had recorded for around 1957/58, though the new tapes were flawed, and eventually destroyed in a fire.
In 1968, Barry found work from Nashville as a session musician, and signed a contract with Nugget Records (2). He recorded six tracks for the label before leaving music due to a quarrel with the Nugget management, after which Barry refused to record for them, and in return, they refused to release him from the five-year contract, so he returned to work on the off-shore oil platforms in Louisiana.
Barry returned to music in 1976, releasing a full-length, self-titled country album, followed with an album of original gospel tunes in 1980, "Sweet Rose of Sharon". Health problems prevented him from continuing a career in music later in his life until 2003, when he released his last album, "Been Down that Muddy Road", which took several years of overdubbing to complete due to his physical limitations.
During his career he also occasionally recorded under his real name and as "Roosevelt Jones".