One episode was originally supposed to feature Hilton and Richie working in a school, but the episode was never made because parents complained.
Originally, the producers wanted Paris Hilton's sister Nicky Rothschild to star in the show with her. When Nicky turned it down, the producers offered Hilton's longtime friend, Nicole Richie, the opportunity to star in it with her, and Richie accepted.
After production of the third season wrapped, the producers had plans to send Hilton and Richie to Mexico for the fourth season, but they had to change their plans when Hilton publicly announced that she and Richie were no longer friends. Hilton asked the producers to replace Richie with her friend Kimberly Stewart, but as Hilton and Richie were both under contract to do a fourth season together, Hilton's request was refused. The fourth season went ahead with an altered format: Instead of traveling together, each episode features Hilton and Richie separately playing "mother" to a different family, with the family then deciding which of them was better in the role.
Paris Hilton stated in a 2006 interview that the show was mostly scripted, and the version of herself she played was based on Legally Blonde (2001) and Clueless (1995).
The artwork for season one, featuring Hilton and Richie with a pitchfork in hand, wearing farm gear, and facing the camera somberly is a parody of Grant Wood's famous painting "American Gothic."