Glenn Close, who was directed by Josh Weinstein, was convinced to do the episode partially because of James L. Brooks. Mona Simpson was designed in a way so that she would somewhat resemble Homer in her face, such as the shape of her upper lip and her nose. There were several design changes because the directors were trying to make her an attractive older and younger woman, but still be Simpson-esque. The inspiration for the character comes from Bernardine Dohrn of the Weather Underground, although the writers acknowledge that several people fit her description. Mona Simpson's crime was intentionally the least violent crime the writers could think of, as she did not harm anyone and was only caught because she came back to help Mr. Burns. The character was named after Richard Appel's wife at the time, the novelist Mona Simpson. When Mona gets in the van, her voice is done by Pamela Hayden because Close could not say "d'oh!" properly and thus they used the original temp track recorded by Hayden.