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Following his 1937 appearances on The Rudy Vallee Show, Skelton transitioned to a regular role in 1939 on NBC's Avalon Time, sponsored by Avalon Cigarettes. On October 7, 1941, he launched his own radio show, The Raleigh Cigarette Program, introducing a captivating array of recurring characters. Among them were the punch-drunk boxer Cauliflower McPugg, the inebriated Willie Lump-Lump, and the endearing "mean widdle kid" Junior, whose catchphrase ("I dood it!") seamlessly integrated into the American lexicon.
The show featured a cast of memorable characters, including the cunning con man San Fernando Red and his pair of crosseyed seagulls, Gertrude and Heathcliffe. Another standout was Clem Kadiddlehopper, a singing cabdriver and country bumpkin with a generous heart and a deliberate simplicity. Clem unwittingly stole the spotlight from high society slickers, much to the chagrin of his cynical father, who once remarked, "When the stork brought you, Clem, I shoulda shot him on sight!"
In addition to entertaining audiences, Skelton actively contributed to the war effort during WWII by promoting the sale of war bonds on his highly rated show. The program boasted a stellar supporting cast, including Ozzie and Harriet Nelson, alongside the Ozzie Nelson Orchestra and announcer Truman Bradley, with Harriet Nelson serving as the show's vocalist.