Pop culture obsessives writing for the pop culture obsessed.
Pop culture obsessives writing for the pop culture obsessed.

Lizz Winstead: Lizz Free Or Die

In the memoir Lizz Free Or Die, writer-comedian Lizz Winstead describes her life and career in a series of chronologically ordered non-fiction chapters, none of which seems designed to stand on its own. Yet Winstead goes out of her way, in the introduction, to insist that it’s “not a memoir, per se.” Maybe she hasn’t read many memoirs. Or maybe she has a deep attachment to the creation of grating, unfunny mash-up words that an editor should have talked her out of: she refers to the chapters of her book as “messays,” which draw upon her “Lizzmemories.” (Other genetic mutations littering up the text include “Foxogenarian,” “awkfidence,” “taboondocks”—a topic of conversation so unexpected and uncomfortable that few people ever go there—and, in the section on how humor helped her deal with her father’s impending death, “dielarity.”


Winstead’s career is fascinating mainly for its Zelig (or “six degrees of separation”) quality. She’s probably best known as co-creator of The Daily Show, where she served as on-air talent. There, she lost a lot of battles with the network over the show’s direction and content, and she left shortly after an ugly incident in which original Daily Show host Craig Kilborn derided the women on staff in an Esquire interview, saying of Winstead, “If I wanted her to blow me, she would.” Several years later, she co-founded Air America and helped discover Rachel Maddow, with whom she co-hosted Unfiltered for a year, before the network dumped Winstead and gave Maddow her own self-titled show. Winstead repeatedly insists that she prefers to focus on her successes rather than her disappointments—and in The Daily Show’s case, to take pride in how, after she left, other people turned her baby into exactly the show she’d always meant it to be.

Winstead’s positive-thinking approach may be psychologically healthy, but it prevents her from offering what any funny person who’s made it in show business ought to be able to provide: hilarious-awful stories about her hard road up from Nowheresville. Even a story about a technical malfunction that left her stranded onstage with her “ill-tended girly garden” exposed turns into an uplifting empowerment fable when she cracks a joke about her situation and is gratified to hear the sound of an audience laughing with her instead of at her. To hear her tell it, people have been falling on the floor laughing ever since she first opened her mouth onstage, and if any of them ever stopped, it’s because they couldn’t deal with a strong woman with a microphone. This attitude would be more convincing if she didn’t cite, as an example of one of the “good, solid jokes” that only a sexist could fail to roar at, the line, “I’m telling you, when you play Monopoly with bald guys, they always choose the hat.”

Much of the time, Winstead comes across as the prototype for the stereotypical smug, self-congratulatory celebrity liberal whom smug, self-congratulatory celebrity conservatives love to complain about, and one who—the ultimate sin—seems awfully deluded about how funny she is. (She dates her decision to do overtly political comedy from a bad date in 1991, when she sat in a bar cracking jokes about the propagandistic CNN coverage of the first Gulf War, and noticed her date was the only person who wasn’t laughing. The line that had all the drunks in stitches? With CNN looking for so many generals to interview, “I am waiting for them to interview a plate of General Tso’s chicken.”)

Actually, readers who pick this book up hoping to read about Winstead’s side of the story recounting The Daily Show’s growing pains may decide the ultimate sin is the way, having come on as a hell-raising truth-teller, she glosses it over without even getting into her problems with Kilborn, which are a matter of public record and predated that Esquire interview. She writes only that the reasons for her departure from the show “are far less important than my wonderful experience of creating and bringing it to life.” Winstead may fancy herself a political satirist, but she writes like a politician.