In this intimate portrait, iconic and legendary artist, Cindy Sherman, reveals her childhood preoccupation with family photos, the reason behind her use of photography, and what challenges she has overcome in her four decades plus career. With self-effacing charm and candor she confesses to competitiveness with male painters, collectors' initial rejection of her work and how her personal shyness drove her to play with costume and identity. Shot on location in her Tribeca and East Hampton, NY studios, Cindy Sherman: Picture This reveals a side of the enigmatic artist rarely seen on film.