Waltrip was born in Owensboro, Kentucky, and began racing go-karts at the age of twelve, entering his first stock car race four years later. He found early success on the asphalt short tracks of Tennessee, winning two track championships at the Fairgrounds Speedway in Nashville and accumulating an all-time record 67 wins at that facility across all sanctioning bodies. His ability to promote the sport through local television and radio appearances gained the attention of car owners and helped him leverage his Nashville success into NASCAR's national ranks.
Waltrip made his Cup debut on May 7, 1972, at the Winston 500 at Talladega in a car he purchased and prepared himself. He drove primarily his own equipment until mid-1975, when he joined the DiGard Racing team. During the DiGard years (1975–1980) he won consistently, including six victories in both 1977 and 1978 working with legendary crew chief Buddy Parrott, and finished runner-up in the 1979 championship — losing to Richard Petty by just eleven points in one of the closest title battles in NASCAR history. His aggressive style earned him the nickname "Jaws," given by rival Cale Yarborough.
The move to Junior Johnson's team for 1981 proved transformative. Waltrip won twelve races in each of his first two seasons with Johnson, claiming back-to-back championships in 1981 and 1982 — both decided by late-season charges that overcame deficits to Bobby Allison. A third championship came in 1985, completing 43 wins across six seasons with Johnson. During this stretch he dominated Bristol Motor Speedway like no driver before or since, winning twelve Cup races there including seven consecutive from 1981 to 1984.
A serious crash at the 1983 Daytona 500 — where his car struck an embankment at nearly 200 mph, was thrown back across the track, and hit the outside wall again — became a turning point. The accident and the public's reaction to it prompted Waltrip to actively rebuild his relationship with fans. He later converted to Christianity in 1983, though he noted it was years before that faith became central to his life.
After joining Hendrick Motorsports in 1987, Waltrip achieved his crowning individual moment: the 1989 Daytona 500. On a fuel conservation strategy devised with crew chief Jeff Hammond, he made his final pit stop 53 laps from the finish — further than most cars could travel on a full tank — and feathered the throttle to reach the checkered flag without another stop. His exuberant post-race celebration in Victory Lane, shouting "I won the Daytona 500!", became one of the most replayed moments in the race's history. He won six races in 1989 and was voted NASCAR's Most Popular Driver by fans in both 1989 and 1990.
Waltrip formed his own team in 1991 and added three more wins, including the 1992 Mountain Dew Southern 500 at Darlington — the one major that had eluded him throughout his career. That win was his 84th and final Cup victory. His career totals across 809 starts include 271 top-fives and 390 top-tens, and he became the first NASCAR driver to earn more than $10 million in career race winnings.
Waltrip joined Fox Sports as their lead NASCAR analyst in 2001, the year his younger brother Michael Waltrip won the Daytona 500 — a victory immediately overshadowed by the fatal crash of Dale Earnhardt, a close friend, on the final lap. Waltrip's visible grief and his subsequent advocacy for mandatory head-and-neck restraints marked him as a credible safety voice in the sport's darkest moment. He pushed successfully for mandatory HANS device adoption, demonstrating the device on air and publicly pressing NASCAR officials for answers about driver safety standards.
His broadcast catchphrase — "Boogity, boogity, boogity, let's go racing boys!" — became one of the most recognizable phrases in American motorsport. He also became known for colorful commentary language including "coop-petetion" and "using the chrome horn." Waltrip retired from the broadcast booth at the conclusion of Fox's 2019 NASCAR schedule.
Waltrip was inducted into the Motorsports Hall of Fame of America in 2003, the International Motorsports Hall of Fame in 2005, and the NASCAR Hall of Fame in 2012. He was named one of NASCAR's 50 Greatest Drivers in 1998 and received NASCAR's "Driver of the Decade" designation for the 1980s. His 59 career Cup pole positions rank fifth all-time, including all-time modern-era records of 35 on short tracks and eight on road courses. In retirement, Waltrip has owned Honda, Volvo, Subaru, and Buick/GMC dealerships in Franklin, Tennessee, in partnership with former car owner Rick Hendrick. He also provided the voice of Darrell Cartrip, an anthropomorphic car version of himself, in all three films of Pixar's Cars franchise.