Tami Erin was selected for the title role out of over 8,000 actresses worldwide for her talents, which include singing, dancing, gymnastics/tumbling and horseback riding.
Producer Gary Mehlman became fascinated with Pippi Longstocking ever since his daughters Romy Mehlman and Alexandra Gurule (nee Mehlman) watched the US dubs of the Pippi Longstocking (1969) TV series (compilations) and movies on VHS rentals (by Video Gems). Inspired by this, Gary began vying for the rights to produce a Pippi film as far back as 1983, but Astrid Lindgren, the author of the Pippi books, was adamantly reluctant to cooperate, feeling that Pippi was like her own child, and was very uncomfortable with Pippi being in Hollywood territory. On the other hand, Svensk Filmindustri, the Swedish studio that owned the production rights to Pippi (and produced the aforementioned TV series/movies), was interested in a possible foreign co-production, but only with Astrid's approval, out of respect. Eventually, in 1985, after a meeting in Stockholm, Astrid agreed to allow Gary to produce a Pippi film, after she hugged his daughters Romy and Alexandra (8 and 7, respectively, at the time), who visited her with their father. Both little girls were credited in the closing credits as the ones "whose love for "PIPPI" provided the inspiration for this film."
As of 2011, the Fernandina Beach house used for Villa Villekulla, Pippi's home, is now Posada San Carlos, a bed and breakfast inn. Painted white, pink, and green, it has also become a popular tourist attraction.
Fay Masterson was one of the runner-ups in the casting search to play the role of Pippi. Ken Annakin liked her so much that he wrote the part of the head girl at the children's home just for her.