Despite the film's success, screenwriter Frank Tashlin said in an interview with Peter Bogdanovich: "After seeing the preview of it, I could've shot Norman Z. McLeod. I'd written it as a satire on The Virginian (1929), and it was completely botched. I could've killed that guy. And I realized then that I must direct my own stuff."
Though the story here is fictional, there was a real dentist who called himself 'Painless' - 'Painless Parker'. Edgar Parker was a dentist who struggled to run a street dental business, and so he took his practice on the road. He worked in the 1890s, in the era of 'amusement'. Inspired by P.T. Barnum, he had a horse-drawn office, show girls and buglers. Parker promised that he could extract a rotten tooth painlessly for 50 cents. If the extraction was not painless, he would give the customer $5.00. Parker had a band that he used to attract people to his office. The band also served to distract the patients and to drown out any moans of pain emitted from the patients. Patients were served with a cup of whiskey or a solution of cocaine (called 'hydrocaine'). Parker is said to have legally changed his first name to 'Painless' to avoid charges of false advertising.
This was the second movie where Bob Hope performed the Academy Award winning Best Original Song, in this case "Buttons and Bows." The first was his theme song, "Thanks for the Memory", which he sang in The Big Broadcast of 1938.