On June 1, 1931, Skelton married Edna Marie Stillwell (1915–1982), a joke writer, business manager, and former usher at Kansas City's old Pantages Theater.[9] Skelton was one month away from his 18th birthday, and Edna was 16. The two met when she approached Skelton after a show and told him she didn't like his material; Skelton asked her if she could do better. They married a short time later, with Edna taking on the tasks of managing her husband and writing for him, as well as becoming part of his act. At first, Skelton considered his wife to be interfering after she saw the boss when his salary was about to be cut. When she came away with not only a raise for her husband but additional considerations as well, Skelton no longer minded Edna's intervention. Since Skelton had left school at an early age, his wife bought textbooks and taught Skelton what he had missed. With Edna's help, Skelton received a high school equivalency degree.
She was also part of the cast for Skelton's Avalon Time radio program under her maiden name of Edna Stillwell.[89] Edna developed a system for working with the show's writers; she would select material from them, add her own and file the unused bits and lines for future use.
In 1942, Edna announced that she was leaving the Skelton home but would continue to manage Skelton's career and write material for him. Skelton did not realize she was serious until Edna issued a statement about the impending divorce through NBC, Skelton's radio employer.[91] They divorced in 1943, leaving the courtroom arm in arm.
After their marriage ended, Stillwell remained an advisor on his career until 1952, receiving a generous weekly salary for life for her efforts