- 1944 (7 years old) | 1944
A few months after Bobby’s second movie was released in theaters, The Fighting Sullivans, in the fall of 1944, when Bobby was seven, he had two interviews at Disney Studios. This resulted in Bobby being contracted by Disney in early December of 1944 to play the leading role of Johnny in Song of the South. This contract would only be for 13 weeks but would be reinstated constantly until its early termination in 1953.
- 1945 (8 years old) | 1945
By the fall of 1945, Bobby was loaned to RKO for the films, From This Day Forward and Universal Studios for So Goes My Love.
- 1946 (9 years old) | 1946
In 1946 Bobby was loaned out to Paramount for O.S.S. and appeared in the Disney films, So Dear to My Heart and Song of the South.
- 1947 (10 years old) | 1947
In 1947 at ten years old, Bobby was loaned out to RKO for If You Knew Susie. Filming of The Window began in New York City that November.
- 1948 (11 years old) | 1948
In 1948, when Bobby was 11 years old, he began performing live radio.
- 1949 (12 years old) | 1949
Two weeks shy of Bobby’s 12th birthday in 1949, he was signed to a new 7-year contract with Disney that was to end in 1956, though terminated early in the spring of 1953. That summer, filming of Treasure Island began in England.
- 1950 (13 years old) | 1950
At 13, Bobby won a Juvenile Oscar on March 23,1950, at the 22nd Academy Award Ceremony as the outstanding juvenile actor of 1949. He was recognized for his outstanding performance in two feature films: The Window and So Dear to My Heart. Some of his radio performances took place that year, and the production of Peter Pan was beginning. Bobby was also loaned to Horizon Pictures for When I Grow Up in the fall.
- 1951 (14 years old) | 1951
In 1951 when Bobby was 14 years old, story meetings, recordings, and live-action rehearsals for Peter Pan took place. By February, a 52-week option for Bobby’s contract at Disney was not picked up, and future payments began on daily vouchers. That autumn, Bobby entered the 9th grade at Hollywood Professional School, which served child movie actors.
- 1952 (15 years old) | 1952
For the first two months of 1952, Bobby filmed The Happy Time. After the filming of The Happy Time concluded, at the age of 15, Driscoll’s parents withdrew him from the Hollywood Professional School and sent him to the public Westwood University High School instead. Bobby continued to Westwood University High School, where he spent the remainder of his freshman year of high school.
- 1953 (16 years old) | 1953
Sometime in late March or early April, shortly after the release of Peter Pan, when Bobby was only 16 years old, Bobby’s contract with Disney was terminated. Bobby still attend Westwood University High, where his grades dropped substantially, and other students ridiculed him for his previous film career and short stature. He began to get beat up by the other students. Due to the constant bullying at Westwood, he befriended a gang of schoolmates for protection and started to take drugs to fit in and presumably deal with the pain of being let go by Disney.
Bobby started using marijuana in the spring of this year.