Waltrip was an active NASCAR driver from 1972 to 2000.  He won three Nextel Cup titles (1981, 1982, 1985), the 1989 Daytona 500, 1992 Southern 500, and is the undisputed Memorial Day major race record holder, having won an unprecedented five Coca-Cola 600 titles. His 84 Winston Cup race wins are the most by any driver in NASCAR's modern (post-1971) schedule format.  

As he moved into the Cup level in the 1970's, his aggressive driving and outspoken style earned him the nickname "Jaws", a reference to the 1975 film about a killer shark. 

His final career win came in 1992, ironically in NASCAR's Florentine classic at Darlington, SC in the Mountain Dew Southern 500, his only win in NASCAR's fourth major, and making him the fourth (of six) drivers to clinch a Career Grand Slam by winning each of the four majors. Overall, he had nine wins in majors.

After his retirement in 2000, Waltrip signed with Fox to be their lead NASCAR analyst and race commentator. Waltrip has also been an analyst for Speed TV. On June 14, 2011, Waltrip was selected to the NASCAR Hall of Fame.