Created and written by McEnany and fellow Chicago improv mainstay Tim Mason, with filmmaker Lilly Wachowski as an executive producer, Showtime’s dark comedy has been hailed as the most radical queer show on TV — if for no other reason than its lead character (played by McEnany) is a gray-haired, middle-aged self-described fat, queer dyke who struggles with depression and anxiety. Early last year, the network ordered a second season of Work in Progress, which is being shot and produced entirely in Chicago. The show’s early success suggests its power lies not so much in subverting Hollywood’s beauty standards as in changing them altogether. Read more: How I Stood Up to Power