How an independent pilot from Chicago got Lilly Wachowski, Julia Sweeney, and Showtime on board

Since its announcement, Showtime’s new comedy Work In Progress has garnered plenty of attention due to the fact The Matrix’s Lilly Wachowski would co-write and co-showrun the series—her first project since leaving Sense8 under her sister Lana’s care after the first season. But before Lily, and before Showtime, Work Of Progress was an independent pilot from Tim Mason and its star Abby McEnany, two beloved mainstays of Chicago’s improv comedy community. Inspired by McEnany’s one-person show, Work In Progress is the story of a self-proclaimed “fat, queer, dyke” who’s life is turned around by an unexpected relationship. During this past summer’s TCA Press Tour in Beverly Hills—at which McEnany was rightfully heralded a “breakout star” by THR—we sat down with the series’ showrunner trio to find out how the project came together, and how they hope the show encourages us to not be afraid to learn from our mistakes. They also explained how they brought Saturday Night Live’s Julia Sweeney into the fold, and how her involvement leads to a healing dialogue about the complicated history between her infamous SNL character Pat and the LGBTQ community. If the insightfulness and joy emanating from McEnany, Mason, and Wachowski is any indication, then Work In Progress will certainly be a new series worth tuning in for.