Weatherly's competitive career began on two wheels. He won three American Motorcycle Association national championships between 1946 and 1950, including the prestigious Laconia Classic 100 Mile road race in 1948. He was inducted into the AMA Motorcycle Hall of Fame in 1998.
Weatherly was celebrated as much for his personality as for his driving. He took practice laps at a NASCAR race wearing a Peter Pan suit. He frequently stayed out partying through the early hours, usually with his close friend and fellow driver Curtis Turner, a combination that earned the pair a legendary reputation off the track. At a 1956 Raleigh convertible-series race, when his engine failed with the crowd watching, he arranged for Ralph Liguori to push his car from behind, and crossed the finish line standing upright in what he called a "chariot of fire." This showmanship was characteristic.
Weatherly began racing cars in 1950. He entered his first modified event and won it, then won 49 of 83 races he entered that season. In 1952 and 1953 he won the NASCAR Modified National championship in successive years, piling up 49 and 52 wins respectively across those seasons. He held a partial interest in what would later become Richmond International Raceway from 1955 to 1956.
He moved into the NASCAR Grand National series in 1956, driving for Pete DePaolo Engineering in a factory-sponsored Ford, then for Holman Moody for two seasons. Through 1959 he recorded consistent top-five and top-ten finishes. He won NASCAR's Most Popular Driver Award in 1961.
His championship years came driving for Bud Moore Engineering. Moore's operation lacked the resources to contest every race, so Weatherly frequently supplemented his schedule by accepting rides with other teams — a practice that became a signature of his approach to the title chase. He won back-to-back Grand National championships in 1962 and 1963, managing the points game with pragmatic consistency rather than dominating race counts.
On January 19, 1964, Weatherly was fatally injured at the fifth race of the 1964 season at Riverside International Raceway in California. His head went outside the car and struck a retaining wall, killing him instantly. Weatherly had refused to wear a shoulder harness and had not installed a window net, because he feared being trapped in a burning car — a concern that ultimately made no difference but underlines the impossible safety trade-offs drivers navigated in that era.
Weatherly was the first driver to die during the season following his championship. The only comparable case since has been 1992 champion Alan Kulwicki, who was killed in a plane crash early in the 1993 season. Weatherly's fatal crash, combined with Richard Petty's accident at Darlington in 1970, eventually persuaded NASCAR to mandate the window net for all competitors in 1971, seven years after Weatherly's death.
Weatherly's grave marker is a sculpture of Riverside Raceway with a checkered flag marking the spot of his fatal crash. He was named one of NASCAR's 50 Greatest Drivers in 1998 and one of NASCAR's 75 Greatest Drivers in 2023. He was inducted into the Motorsports Hall of Fame of America in 2009 and the NASCAR Hall of Fame on January 30, 2015. His two consecutive championships, won without a fully resourced operation, and his extraordinary personality left a mark on NASCAR that persisted long after his death.