In preparation for the 1939 Bing Crosby movie The Star Maker, Paramount casting agents, led by Leroy Prinz, interviewed over 1000 children. Hickman won one of the parts in the film. Pleased with Hickman's performance, Crosby notified his older brother and talent agent Everett Crosby of the young actor. After this, he went on to appear in multiple motion pictures throughout the 1930s and 1940s in a wide array of genres. A busy performer, he would sometimes work at different films simultaneously.