Weatherly enjoyed behaving outrageously. He once took practice laps wearing a Peter Pan suit. Moreover, he frequently stayed out partying until the early hours, usually with fellow driver and friend Curtis Turner. This behavior earned him the nickname the "Clown Prince of Racing". In 1956 at Raleigh, while racing in the convertible series, Weatherly's engine blew. With the help of Ralph Liguori pushing from behind, he displayed showmanship to the fullest extent by crossing the finish line while standing in a "chariot of fire".
Weatherly began racing cars in 1950. "Little Joe" won the first modified event that he entered. He won 49 of the 83 car races that he entered that season. In 1952 he won the NASCAR Modified National crown, and he again won 49 of 83 car races that he entered. Weatherly won 52 more races in 1953, and won the Modified National crown again. Weatherly had partial interest in what would later be called Richmond International Raceway from 1955 to 1956. In 1956 he moved into the NASCAR Grand National series. He drove a factory-sponsored Ford car for Pete DePaolo Engineering. For the next two seasons, Weatherly drove for Holman Moody. In 1959, Weatherly recorded six top-5 finishes and ten top-10s. He narrowly lost the 1959 Hickory 250 to Junior Johnson; being outlapped twice before the race was concluded. Weatherly won NASCAR's Most Popular Driver Award in 1961. He won two consecutive championships, in 1962 and 1963, for Bud Moore Engineering. Moore did not have enough resources to run the full season, so Weatherly frequently "bummed a ride".
Death
Weatherly died on January 19, 1964, from head injuries sustained in a racing accident at the fifth race of the 1964 season, at Riverside International Raceway. His head went outside the car and struck a retaining wall, killing him instantly. Weatherly was not wearing a shoulder harness, and did not have a window net installed on his vehicle, because he was afraid of being trapped in a burning car. He is one of two reigning champions of the NASCAR Cup Series to die during a season as the defending champion and the only one to die during a race. Weatherly's fatal crash, combined with Richard Petty's crash at Darlington in 1970, eventually led NASCAR to mandate the window net seven years later, in 1971. Weatherly's grave marker is a sculpture of Riverside Raceway, with a checkered flag marking the spot of his fatal crash.