Dennis Gentry was born in Lubbock, Texas, and attended Dunbar High School. He played football for the Bears of Baylor University. Drafted by the Bears in 1982, he played 11 seasons for the team, all under Head Coach Mike Ditka. Gentry was a wide receiver and running back, and took on various assignments on special teams including kick returner. He was a member of the 1985 Bears Championship Team that won Super Bowl XX. Gentry had 171 receptions for 2,076 yards and 7 touchdowns. He rushed 237 times for 767 yards and 5 touchdowns. Gentry also returned kicks and had 192 returns for 4,353 and 3 touchdowns.