According to Orson Welles, this film grew out of an act of pure desperation. Welles, whose Mercury Theatre company produced a musical version of "Around the World in 80 Days," was in desperate need of money just before the Boston preview. Mere hours before the show was due to open, the costumes had been impounded and unless Welles could come up with $55,000 to pay outstanding debts, the performance would have to be canceled. Stumbling upon a copy of "If I Die Before I Wake," the novel upon which this film is based, Welles phoned Harry Cohn, instructing him to buy the rights to the novel and offering to write, direct and star in the film so long as Cohn would send $55,000 to Boston within two hours. The money arrived, and the production went on as planned.
Everett Sloane refused to wear the leg braces constructed for his character, complaining bitterly of the pain they caused. Sloane was reportedly impossible to deal with and shunned everyone on the set.
Near the end of shooting, Orson Welles told Columbia executives that he wanted a complete set repainted on a Saturday for shooting on Monday. Columbia exec Jack Fier told Welles it was impossible, because of union rules and the expense that would be incurred by calling in a crew of painters to work on a weekend. Welles and several friends broke into the paint department that Saturday and repainted the set themselves, and when they were finished they hung a banner on the set that read "The Only Thing We Have to Fear is Fier Himself." When the union painters arrived at work on Monday and saw that the set had been repainted by someone else, they refused to work, threw a picket line around the studio and threatened to stay on strike until a union crew was paid triple time for the work that had been done (which was why Fier had refused to authorize the work in the first place). To placate the union, Fier agreed to pay them what they wanted but put the cost on Welles' personal bill. In addition, he had the union painters paint a banner saying "All's Well That Ends Welles."
Columbia Pictures boss Harry Cohn told Orson Welles he would never again hire one man to produce, direct and act because he could never fire him.
Orson Welles' original rough cut of this picture ran 155 minutes. Numerous cuts made by Columbia Pictures executives included a shortening of the famous funhouse finale.