Bubba's interest in racing and motorbikes began at a young age. His father, James Stewart Jr., was so passionate about racing that he took his son Bubba on a ride just two days after he was born. Bubba started dirt biking at the age of three, and a year later, at the age of four, he finished his first race. He continued to compete regularly as a child and won several races, including one against drivers who were ten years older than him. His father saw such potential in his son that he didn't put any restrictions on Bubba's hobbies or activities. He allowed him to spend all his time riding motorcycles if he wanted to. And because of this open-minded approach, Bubba grew up loving bikes and racing them constantly from a very young age. When Bubba turned ten, he and his father went to work for another driver as his assistants during practice and races. This gave Bubba the opportunity to learn how to drive competitively by watching others drive and make adjustments accordingly. Soon afterwards, James Sr. became ill and died at the age of fifty-two. Without its father figure around to guide him, Bubba decided not to continue driving anymore. However, one of his friends convinced him to start racing again since there were many different types of races available and it wouldn't be hard to find something new to try out. So, Bubba returned to the track and soon found himself finishing high in almost every race he entered.