Stricklin grew up in Calera, Alabama. He married Pam Allison, the daughter of NASCAR legend Donnie Allison after they were introduced by her cousin Davey. Stricklin was the last member of the Alabama Gang.

In 1987, Stricklin won NASCAR's Dash Series championship and made his debut in the Winston Cup Series.

Two years later, he finished second to Dick Trickle in the NASCAR Rookie of the Year competition with car owner Rod Osterlund. In his sophomore season, he competed in only three events before taking over the driving chores of Bobby Allison's No. 12 Raybestos Brakes-sponsored Buick. 1991 turned out to be one of his best seasons, as he finished 16th in points as well as a career high second-place finish, at Michigan International Speedway. With eight races left in the 1992 season, Stricklin left Allison's team and after a few races driving for Junie Donlavey, he picked up a ride for 1993 with Junior Johnson, driving the No. 27 McDonald's-sponsored Ford. In 1994, Stricklin paired with owner Travis Carter to form a new team, the No. 23 Camel Cigarettes-sponsored Ford. It was a disappointing year for Stricklin, finishing 26th in points.

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