Aileen Quinn – 47
A list of classic musicals would be incomplete without the inclusion of Annie. The 1982 Broadway hit was headed by none other than Aileen Quinn who captured the essence of the character, along with the heart of people everywhere. After her sudden spike to stardom, Aileen starred in several Hollywood films (her most popular role being Annie Bennett Warbucks in Annie) before receding from the industry to spend more serene days as a teacher. Her last role was as Dr. Quinn in two episodes of The Comeback Kids in 2014.