Dupree's first language was actually French but he learned English and ultimately became the family's breadwinner due to his all-American talent at a young age.
There, a twelve year old Dupree enrolled in Meglin's Dance School, which at the time was known for sending their top students to motion picture studios for movie and stage auditions.
In 1941, Roland's career truly began to thrive when Universal Studios developed a tap-dancing group called the "Jivin' Jacks and Jills".
[3] Others in the group included Joyce Horne, Tommy Rall, Jimmy Vecchio, Robert Scheerer, Jane Adams, Kathleen Hughes, Susanna Foster, Peggy Moran, Mary Ellen Kay, Kristine Miller, Mala Powers, and Donna Martell.
After being in nearly ten films as a dancer and vocalist, Dupree decided to give acting a go and, after many auditions, he was cast as Shirley Temple's boyfriend, Joey, in Miss Annie Rooney.
This eventually led to a contract at Metro-Goldwyn-Mayer Studios where, after being cast in many minor parts, he was given the role of Jerry, Ann Southern's love-sick bellhop in the film Maisie Goes To Reno.
[1] One of Dupree's jazz students, Margaret Kerry, became the reference model for Tinker Bell for Walt Disney's Peter Pan.
[1][6] Once Roland's employment options were quite limited, he decided to create his own job by hiring two female dancers and choreographing a dance act called "The Dupree Trio".