At age 11, Waltrip already knew what he wanted to be when he grew up. He would follow his dream to become an established race car driver like his older brother Darrell.
Starting out, the younger Waltrip spent the early part of his career racing go-karts in Kentucky, Indiana and Tennessee. His stock car racing took off in 1981, when he won the Mini-Modified division track championship at Kentucky Motor Speedway.
Success came easy for Waltrip, and as he became older it happened quite often. In 1983, he won the NASCAR Dash Series championship. Afterwards, he made the move to North Carolina to advance his career. When Waltrip first moved to North Carolina, he resided with Richard and Lynda Petty. The Petty's helped Waltrip establish his roots in racing country. Waltrip credits Richard with not only his first job, but with the advice and guidance that prepared him for his future as a successful driver and car owner.
In 1985, Waltrip made five NASCAR Sprint Cup Series starts for Dick Bahre debuting at Lowe's Motor Speedway in May. The next year Waltrip completed his first full season in Cup finishing 19th in the points standings driving for Bahre. Then, Waltrip drove for Chuck Rider from 1987 to 1995 and Wood Brothers from 1996 to 1998.
Waltrip drove for Jim Smith from 1999 to 2000 in the NASCAR Cup Series and for Dale Earnhardt Inc. from 2001 to 2005.
For Waltrip, 2001 started off exactly as he and team owner Dale Earnhardt had dreamed. After moving into a high-profile ride with Dale Earnhardt, Inc., Waltrip ended his 462-race winless streak in the Cup Series with a win in the Daytona 500.
Earnhardt's death in a crash on the final lap of that race not only tarnished Waltrip's achievement, but changed the face of the sport forever.
His win at Daytona, an emotional second-place finish to teammate Dale Earnhardt Jr. in Daytona's Pepsi 400 and a resounding second-place finish in the penultimate race at Homestead were the only top-10 finishes he mustered all season.
Waltrip was one of the best drivers in the midseason of 2002, but he struggled early in the year. A win in the Pepsi 400 was his second career victory, and he finished 14th in the standings -- 10 spots higher than his finish in 2001.
In 2003, Waltrip won the Daytona 500 for the second time in three seasons, becoming one of only eight drivers to win the series' most prestigious race two or more times. He also recorded his first multiple-win season of his career by adding a victory at Talladega in September.
Waltrip started a disappointing 2004 season with a wild roll in the grass on the backstrech in the Daytona 500, which led to a 38th-place finish. Waltrip, who finished 20th in the driver standings, scored his best finish (2nd) of the season in the Coca-Cola 600 at Lowe's Motor Speedway.
He raced one more full-time season with DEI in 2005 and managed to post three top fives and seven top 10s with a 25th-place finish in the final point standings.
In 2006, Waltrip-Jasper Racing, a brand new team affiliated with Bill Davis Racing, fielded Waltrip's No. 55 NAPA machine. He failed to qualify for three races that year and didn't post a single top five or top 10 finish.
In 2007 Waltrip set out to field three cars with Toyota's help during the manufacturer's inaugural year. But he struggled as a driver that year and failed to qualify for more races (19) than he ran in (14). He did manage to score one pole position at Talladega and two top-10 finishes that year.
Under Waltrip's watchful eye, MWR showed great promise during the 2008 NASCAR Sprint Cup Series season. Waltrip kicked 2008 off in the No. 55 NAPA Toyota on the outside pole next to three-time NASCAR Sprint Cup Series champion Jimmie Johnson for The Great America Race. In 36 starts, Waltrip was credited with leading 11 different races.
Waltrip’s best finish of the season was a runner-up finish to Kurt Busch in the rain-shortened Lenox Industrial Tools 301 at New Hampshire Motor Speedway. The No. 55 NAPA AUTO PARTS Toyota Camry team earned one top-five, two top-10, five top-20 and 13 top-25 finishes. Waltrip finished 29th in the owner points standings during 2008.
