Playing Through is a fictionalized story honoring the real life sports and civil rights heroine Ann Gregory, the first woman of color to enter a USGA tournament.

In Playing Through, Ann Gregory collides in the USGA Women's Amateur with Babs Whatling, a privileged white woman from the South. The story centers on the women's head-to-head competition in a single match with flashbacks that add rich context to the personal struggles that have shaped each of them. For both Ann and Babs, the game is as much about finding inner strength as it is about overcoming obstacles on the course.

Playing Through was filmed in Sarasota, Florida, in 2021. The story was written by Curtis Jordan, inspired by his mother's actual encounters with Ann Gregory during her golf career in the 1950s. Lead actress Andia Winslow, who portrays Gregory in the film, had heard about Gregory as a child but wondered, with Jordan and others, why her story had yet to be told. Winslow and others involved in the production were instrumental in helping to shape the dialogue to ensure that it honored the voice of Ann Gregory and resonated with people, particularly Black women, who lived through the same era.

Along with well-known talent, including actresses Winslow and Julia Rae and actors Sam Daly, Ronnie Gene Blevins, and Tim Murphy, Playing Through engaged local artists and industry experts in its production. Members of the noted Westcoast Black Theatre Troupe and associates of the Ringling College of Art + Design lent their talents along with many other professionals from Sarasota.