Stricklin is the son-in-law of NASCAR legend Donnie Allison, having married Pam Allison after being introduced to her by his cousin and fellow racer Davey Allison. He is recognized as the last member of the Alabama Gang, the informal grouping of drivers from that state that included Bobby Allison, Donnie Allison, Davey Allison, and Neil Bonnett. In 1987, Stricklin won the NASCAR Dash Series championship and made his debut in what was then the Winston Cup Series.
In 1989, Stricklin finished second to Dick Trickle in the NASCAR Rookie of the Year competition while driving for car owner Rod Osterlund. In his sophomore season he competed in just three events before taking over the driving duties in Bobby Allison's No. 12 Raybestos Brakes Buick. The 1991 season proved one of his strongest, with a 16th-place finish in the championship standings and a career-high second-place result at Michigan International Speedway. With eight races remaining in 1992, Stricklin was released by Allison and finished the season driving for Junie Donlavey.
For 1993, Stricklin signed with Junior Johnson to drive the No. 27 McDonald's Ford. The following year he paired with owner Travis Carter in a new team running the No. 23 Camel Cigarettes Ford, a partnership that yielded a disappointing 26th-place points finish. After failing to secure a ride for 1995, Stricklin served as a consultant for Kenny Bernstein's rookie driver Steve Kinser, the World of Outlaws sprint car champion who was struggling to adapt from dirt to pavement. When Kinser resigned mid-season, Stricklin stepped in as driver and posted five top-ten finishes before the team closed at year's end.
Stricklin joined Stavola Brothers Racing in 1996 to drive the No. 8 Circuit City Ford, recording a second-place finish at Darlington Raceway and finishing 22nd in points. He returned to the Stavola Brothers in 1998 but was released after failing to qualify for the Coca-Cola 600, completing the year as a substitute for David Green and Robert Pressley. In 1999, Stricklin transitioned briefly to crew chief duties for Gary Bradberry's No. 78 Ford before taking over the No. 58 Ford for Scott Barbour's SBIII Motorsports, where he posted a top-ten at Michigan. Despite a verbal commitment from Barbour to carry him through 2003, the team folded after a sponsor issued a bounced check.
Stricklin continued making appearances for Junie Donlavey into 2001, recording a sixth-place finish at Michigan that year. He moved to Bill Davis Racing in 2002, bringing the Hills Brothers sponsorship with him, but was replaced by Kenny Wallace before the Southern 500. That race marked his last Cup appearance.
Hut Stricklin's NASCAR career spans more than fifteen years of Winston Cup competition. His family ties to the Allison dynasty gave him a distinctive place in the Alabama Gang tradition, and his career-best second-place finish at Michigan in 1991 reflected the competitive heights he was capable of reaching. His willingness to step into struggling or underfunded operations throughout the 1990s and early 2000s underscores his adaptability and dedication to the sport.