#2. Jackie Cooper
Age at Awards Show: 9 years, 1 month, 26 days old
Award: Actor (1932) for “Skippy”
After appearing as Skippy in 1932, Jackie Cooper continued on to lead a distinguished career in both the film industry and military. During World War II, he served in the Navy and attained the rank of Captain. He appeared in the first four Superman films, directed TV shows, and earned a star on the Hollywood Walk of Fame. He died in 2011 and was buried with full military honors at Arlington National Cemetery.