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Several actors were offered the role of Wonka before Gene Wilder:
- Joel Grey was first choice for the role of Willy Wonka, but was not considered physically imposing enough.
- Roald Dahl's original choice to play Willy Wonka was Spike Milligan.
- Peter Sellers was desperate to play the role, and even begged Dahl for approval.
- The role was offered to Ron Moody, who declined it.
- Jon Pertwee had to turn down the role because he was in the tight schedule of Doctor Who (1963) at the time.
- Sidney James and Kenneth Williams showed interest in the role.
- Frankie Howerd was offered the role, but scheduling conflicts with Up Pompeii (1971) and The Chastity Belt (1972) forced him to turn down the role.
- Dudley Moore, Peter Cook, and Michael Crawford were also considered for the role.
- All six performing members of Monty Python - Graham Chapman, John Cleese, Eric Idle, Terry Gilliam, Terry Jones, and Michael Palin - had expressed great interest in playing the role, but they were deemed not big enough names for an international audience. Cleese, Idle, and Palin were considered for the same role in Charlie and the Chocolate Factory (2005). Eric Idle recorded the audio version of the book.
After reading the script, Gene Wilder said he would take the role of Willy Wonka under one condition: that he would be allowed to limp and then suddenly somersault in the scene when he first meets the children. When director Mel Stuart asked why, Wilder replied that having Wonka do this meant that "from that time on, no one will know if I'm lying or telling the truth." Stuart asked, "If I say no, you won't do the picture?" Wilder said, "I'm afraid that's the truth."
Ernst Ziegler, who played Grandpa George, was nearly blind (from poison gas in World War I), so he was instructed to look for a red light to guide him when his character was meant to be looking in a specific direction.
Peter Ostrum and the other child actors have stayed close over the years, and regularly attend fan conventions together.
When Gene Wilder died in 2016, Peter Ostrum changed his social media profile to "Former child actor, veterinarian, inherited a chocolate factory on August 29, 2016."
The reactions of the actors and actresses in some scenes are spontaneous: In the scene where Wonka limps out of his factory to greet the Golden Ticket winners, everyone's reaction is genuine. When the children first enter the Chocolate Room and see the candy gardens, their reactions are genuine. When filming the tunnel scene, the actors' reactions to Wonka's singing were genuine; Peter Ostrum, Jack Albertson, and Denise Nickerson were all terrified and had thought Gene Wilder had gone into a psychotic meltdown. In the scene where Wonka is screaming at Charlie and Grandpa Joe, Ostrum's and Albertson's reactions are real. Wilder actually wanted to tell Ostrum beforehand, but director Mel Stuart advised strongly against it, so as not to ruin the illusion of surprise.