Following graduation from college, Barry established the ROBO Car Wash (Morris County Car Wash) in Morristown, New Jersey and Caswell-Massey of Morristown. In 1973, he ran unsuccessfully for the Republican nomination to the State Assembly. Two years later, he won election to the state legislature with the slogan "A Businessman's Approach to Lawmaking." In 1975 he was elected to the General Assembly representing New Jersey's 23rd Legislative District. Barry won re-election to four consecutive terms in office before accepting a gubernatorial appointment in 1982 from the newly elected Governor Thomas Kean to the post of Director of Consumer Affairs, a position previously held by Millicent Fenwick. He served throughout the Kean administration's two terms at which point he left government service and moved to the private sector.