Born Leonard Borisoff and raised in Philadelphia, Barry aspired to become a professional baseball player. When he was in the military, and sang with the Army bands - and was so encouraged by the response of his fellow soldiers - that he decided to make a career in music.
After being discharged, Barry returned home to Philadelphia and joined The Dovells as their lead singer. His is the lead voice on their best selling records "Bristol Stomp," "Hully Gully Baby" and "You Can't Sit Down," among others. "Bristol Stomp" sold over one million copies, and was awarded a gold disc.
Barry also made film appearances with The Dovells in films such as Don't Knock the Twist, as well as guest appearances on television on The Dick Clark Show, Shindig, and Hullabaloo. Soon after leaving the group, Barry recorded his first solo single "Lip Sync."
As a predominately blue-eyed soul singer, he recorded two hits in 1965 for Decca Records in the US and released by Brunswick Records in the UK: "1-2-3," and "Like a Baby," both of which made the Top Ten of the UK Singles Chart. Those songs also peaked at #2 and #27 on the U.S. Billboard Hot 100 chart respectively.
"1-2-3" sold over one and three quarter million copies, and gave Barry his second gold disc. Both "1-2-3" and "Like a Baby" were composed by Barry, John Madara and Dave White, one of the original Juniors from Danny & the Juniors. Barry also covered "Treat Her Right" by another blue-eyed soul act, Roy Head and the Traits.
In 1969 Barry and Madara co-produced The Original Version: Journey To The Moon LP for Buddah Records. Barry used Madara's studio band (including Daryl Hall of future Hall & Oates fame) that would become Gulliver: Tim Moore on guitar, Tom Sellers on bass, Daryl Hall keyboards, Jim Helmer drums. They were called the Sound of Genesis for the album. It was billed as being recorded live on Earth, in Space and on the Moon. According to Madara, this album "was approved by NASA, who sent in the tapes every day to us of the moon flight, which we used on the LP."
Tom Sellers arranged it and the future Gulliver performed it - this time as The Electric Indian, adding Bobby Eli on guitar and Vince Montana on vibraphone. Montana would go on to fame with MFSB and the Salsoul Orchestra. "Broad Street," the single's B-side, also written and produced by Barry and never issued on an LP, was an instrumental.
Even after his period of hit records ended, Barry continued performing his entertaining stage act, and later moved into songwriting and production work with WMOT Productions.
In May 2008, Barry reinvented himself as a writer with the publication of the semi-biographical novel, Black-Like-Me. The storyline involved a pair of Caucasian siblings growing up in a largely African-American neighborhood, accepted by some, rejected by others.