Leading Lady Parts

Lizz Winstead, who co-created The Daily Show and launched the career of Rachel Maddow, is on to her next legacy: the Vagical Mystery Tour

- Anna Menta

IN 1996, STAND-UP COMEDIAN LIZZ WINSTEAD sat down with producer Madeleine Smithberg to create a comedy show that parodied cable news. The five-year-old Comedy Central loved what they came back with and made Winstead head writer of The Daily Show. Winstead ran the writers’ room and served as correspondent for two years—until then-host Craig Kilborn told Esquire magazine: “To be honest, Lizz does find me very attractive. If I wanted her to blow me, she would.”

It was late 1997, and in those days, repercussions amounted to a one-week suspension for Kilborn. In 1998, Winstead left the show.

One year later, Jon Stewart took over and turned The Daily Show into a political comedy juggernaut. When he retired in 2015, Winstead got a cursory mention in the dozens of eulogies that ran online and in print. It was, she says, “a little bit of a bummer.” On the other hand, if people dismiss or minimize her participation in the show, Winstead has “no problem saying, ‘Yeah, that foundation that Trevor and Jon and everybody built out on? The one that was so malleable and sturdy that they could do that? I made that.’”

Winstead went on to co-found Air America in 2003; the progressive radio network launched Rachel Maddow and the podcast career of Marc Maron. She was fired two years later by a new president, who told her “comedy is not a good tool for social change.” (The company filed for bankruptcy and folded in 2010.)