Kit befriends a former pilot named May Songbird and helps her find the courage to fly her plane again following an incident years ago that caused the original Rocketeer to rescue her. May must get over her fear when Rocketeer's rocket-pack starts leaking after a rock hits it.
May Songbird bares some similarities to Bessie Coleman, the first woman of African-American descent to hold a pilot's license. Both are stunt pilots and are African-American. However, unlike Bessie Coleman, who died in a plane crash, May quit flying out of fear.
Like Bessie Coleman, May Songbird flies a Curtiss JN4 Jenny. A similar biplane appeared in the 1991Rocketeer movie.