3 time Winston Cup champion. 1981, 1982, 198559 career pole positions. 4th on the all time list.Younger brother, Michael Waltrip , currently drives in Nextel Cup.Has won 84 Winston Cup races. Tied with Bobby Allison for 3rd on the all-time win list.In his early days he was always booed by the fans. One day he said "Meet me at The Big K" and we can duke it out". K-Mart later became a sponsor.1981, 1982, and 1985 Winston Cup championHis last race as an owner/driver he drove an all white Chevrolet Monte Carlo called the 'Tim Flock Special'. He donated the prize money to racing legend Tim Flock who was sick at the time to help with medical expenses. Tim's car number in 1955, and 1956 was 300. Darrell wanted to use this number on the car, but NASCAR rules only allow two digit numbers on the cars. So he had to take 300 off of the car, and use his number 17. The next race, he drove for Dale Earnhardt Inc, car number 1, for most of the season until Steve Park recovered from injuries from a crash at Atlanta. The irony here is Darrell, and Dale never really got along with each other before this.Tied for third in NASCAR's all-time win list with Bobby Allison . Hoped to get at least one more win before he retired.Was one of the most hated drivers in motorsports durong the 1970s, but won the most popular driver award in 1989, and 1990.Won the 1989 Daytona 500Brother Michael Waltrip won the 2003 Daytona 500 and the 2003 EA Sports 500 at the Talladega (Alabama) Superspeedway.Has won 84 Winston Cup races. Holds the record for most wins of Charlotte's World 600 with five - 1978-9, 1985, 1988-9.Is fourth on NASCAR's all-time win list with 84 wins.Openly cried when his brother, Michael Waltrip , won the 2001 Daytona 500, but could be heard saying "Is Earnhardt okay?" shortly before they cut to a commercial. Dale Earnhardt , his good friend, had just crashed as the race was concluding and died shortly, thereafter.He and his brother, Michael Waltrip , are the only pair of brothers to both win the Daytona 500.Appointed Honorary Ambassador of Peace for the Harvey Ball Foundation along with Jackie Chan , Brooke Shields , A.V.T. Shankardass , Jerry Lewis , Prince Albert of Monaco , Jack Nicklaus , Greg Norman , Phil Collins , Jimmy Buffett , Dale Earnhardt Jr. , Heather Mills , Yoko Ono , Patch Adams , Sergei Khrushchev and Winnie Mandela .Owns a Volvo/Honda/Pre-Owned car dealership in Franklin, Tennessee