Barry was a 4 sport athlete in high school, achieving varsity letters in football in 1982, ‘83, and ‘84, in basketball in 1983, ‘84, and ‘85, in baseball in 1985, as well as track in 1985.

In football, Barry was the 1984 State Rushing Leader (1,992 yards), this mark also being the Lawrenceburg single-season record until 2012. He also held the single-season Touchdown record (30), which was held until 2012. He was All-State 1st team in 1984, as well as UPI, AP, and Bloomington Herald, 1984 USA Today Honorable Mention All-American. Along with these, Barry was All-Conference and Conference Player of the Year in 1984, as well as 1984 Team Captain and MVP. Barry was a member of the South Indiana All-Star team in 1985. In basketball, Barry was a team captain his junior and senior years, MVP his junior year, All-Conference and All-Sectional, and elected to the 40/8 All-Star game his senior year. In baseball, he was Team MVP, All-Conference, and the EIAC Batting Champion in 1985.

After high school, Barry went on to play football at Indiana University. There, he competed in the 1986 All-American Bowl, the 1987 Peach Bowl, and the 1988 Liberty Bowl. He graduated from IU in 1990.

Barry and his wife, Debbie have 3 sons, Bradley, Cameron, and Carson.