Chris Fleming is best known for his YouTube series Gayle, in which he 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 Melissa Strype, who also plays Gayle's daughter. Fleming's mother co-stars as Bonnie, his best friend and frenemy. Fleming grew up in Stow, Massachusetts.