Sandra Day O'Connor, best known as the first woman to serve on the United States Supreme Court, had a surprising connection to the film world through her appearance in the 1987 documentary *Gap-Toothed Women*. This unique film, which explores the lives and experiences of women with gap-toothed smiles, showcases O'Connor's charisma and depth beyond her judicial career. For collectors, this documentary stands out not just as a piece of film history, but also as an artifact reflecting the evolving narrative around women's representation in both law and media. Collectors actively seek out *Gap-Toothed Women* for its cultural significance and O'Connor's unexpected involvement. The film's limited releases, particularly on VHS and DVD, make it a sought-after item for those interested in the intersection of law, feminism, and film. O'Connor's legacy as a trailblazer in both the courtroom and the arts continues to resonate, making this title a valuable addition to any physical media collection.