Chris Fleming is best known for her YouTube series Gayle, in which she stars as the eponymous character Gayle Waters-Waters. Fleming has been described as a "progressive gender-bending role model" Fleming's comedy is aimed at deconstructing social norms, including masculinity. The 40-episode, absurdist comedy series is written by Fleming and directed by comedian Melissa Strype, who also plays Gayle's daughter, Terry Gross. Gayle is filmed in Fleming's hometown in Massachusetts.