Waltrip is tied for fourth on the NASCAR's all-time wins list in the Cup Series and is only second to Jeff Gordon for the most wins in NASCAR's modern era. He is ranked second for all-time pole positions with 59, including all-time highs with 35 on short tracks and eight on road courses. Waltrip has competed in 809 Cup starts over four decades and 29 years (1972–2000), winning $19,886,666.00 in posted earnings, causing Waltrip to become the first NASCAR driver to be awarded over $10 million in race winnings, more than $26 million in today's currency.
Waltrip has also won many awards in NASCAR. Including two of NASCAR's Most Popular Driver Award (1989, 1990), three "American Driver of the Year" awards (1979, 1981, 1982), "NASCAR's Driver of the Decade" for the 1980s, three "National Motorsports Press Association Driver of the Year" awards (1977, 1981, and 1982), two "Auto Racing Digest Driver of the Year" (1981 and 1982) titles, the first "Tennessee Professional Athlete of the Year" (1979) award, one of NASCAR's 50 Greatest Drivers in 1998, and the Bill France "Award of Excellence" in 2000. He has been inducted into numerous halls of fame, including the Motorsports Hall of Fame of America for 2003 the International Motorsports Hall of Fame for 2005. After being nominated for the inaugural 2010 and 2011 classes, he was inducted into the NASCAR Hall of Fame's 2012 class.
Waltrip gas also served as a color analyst for Fox Sports, was a columnist at Foxsports.com, and became an author. Waltrip retired from the commentary box at the conclusion of Fox's broadcast schedule for the 2019 NASCAR season in June 2019. Darrell Waltrip has a net worth of $25 million dollars.