Bossypants

From the first chapter when a fellow kindergartener rips up her paper and she is forced to enter “the real world” (11), Fey writes of how experiences, observations, and even mistakes impact her view of the world and of herself. Just as she learns about comedy from her colleagues—she dedicates an entire chapter to “Things I Learned from Lorne Michaels” and takes time throughout later chapters to describe comedy techniques she’s learned from Seth Meyers, Alec Baldwin, and others—she takes lessons away from life experiences, always seeking to grow.

Throughout Bossypants, she embraces her mistakes and mishaps because they force her to learn lessons that make her a better person. At Summer Showtime, when she is chastised for intervening in her friend’s romance, she experiences “a major and deeply embarrassing teenage revelation” that she’s been “using [her] gay friends as props” (40). She also sabotages a girl who is dating her ex-boyfriend and later learns that “girl-on-girl sabotage” (37) is some of the “worst kind of female behavior” (38). Fey’s acknowledgment of her mistakes and of their necessity toward self-improvement is also reflected in her perspective on comedy. She writes that “THERE ARE NO MISTAKES, only opportunities” (77) in improv; she also believes the pilot episode of 30 Rock is “awkward, sweaty,” and a “mess” (154), but by the 11th episode it “had really found its voice” (172). Personally and professionally, Fey turns mishaps into learning opportunities. While her comment that “bombing is painful, but it doesn’t kill you” (113) refers specifically to improv, it arguably applies to oneself, as well.

Lessons sometimes come from unexpected places. For example, even though she misses signals from Handsome Robert Wuhl that would have told her he isn’t romantically interested in her, her time with him teaches her she could climb mountains, something she’d never expected to do. Working at the YMCA, she witnesses depressing scenes of human loneliness that inspire her to work her way upward by applying for a promotion and taking improv classes at night. In this way, Bossypants, even when meandering through seemingly unrelated memories, is a collection of events that all together help Fey develop into the person she is today.

Amy Poehler, by cavalierly telling Jimmy Fallon she doesn’t care if he likes her “unladylike” (129) joke, demonstrates to Fey the power of boldly refusing to conform to sexist conventions—and therefore embodies one of the most important lessons of the book. Fey learns early that women are objectified and expected to conform to strict standards of beauty. When she’s 13, a man stuns her by yelling a lewd comment at her from his car; also as a teenager, she learns from her cousin’s judgmental comment about a stranger that “there are an infinite number of things that can be ‘incorrect’ about a woman’s body” (20). Her experiences working in comedy further illustrate the challenges women face in trying to achieve respect and success. In the final chapters, Fey learns that the standards of female beauty and behavior extend to motherhood and that there is, in fact, nothing a woman “must” (220) do.

That the book ends in an open-ended manner—Fey has not yet decided whether to have another baby and suggests that she knows “everything will be fine” (250) even though she doesn’t feel it—is the final illustration of her continuous learning, for she leaves the reader mid-lesson.

In “Introduction,” Fey shares a photo of herself as an awkward child, followed by a photo of herself as a glamorous adult posing in a fancy gown. She writes that her book is “a simple task of retracing [her] steps to figure out what factors contributed to this person developing into this person” (5-6). Recalling a theater party she attended in high school, she snidely remarks how she looks “pretty cool” in her “best Gap turtleneck” (34). At University of Virginia, she is “a wide-hipped, sarcastic Greek girl with short hair that’s permed on top” (53). She also competes for male attention with “sorority girls with their long blond ponytails and hoop earrings” (53). She struggles to read social signals, making a boy from her dorm “literally” (53) run away when she tries to kiss him, and she goes all the way up Old Rag Mountain with Handsome Robert Wuhl before realizing he isn’t romantically interested. In “The Secrets of Mommy’s Beauty,” she writes of her shag haircut, fanny pack, and pimple squeezing.

By sharing her glamorous photo, Fey acknowledges her transformation and illustrates how glamor and success can come from humble beginnings. She also suggests that this awkwardness is normal, not only in youth but also into adulthood. Her glamorous photo shoots take place only after hours of preparation by stylists and makeup artists. Perhaps more importantly, she still believes that “things most people do naturally are often inexplicably difficult for me” (248). The lesson seems to be that physical or social awkwardness, like mistakes, is often unavoidable and not necessarily detrimental to one’s personal life or career.

Bossypants advocates for the acceptance of all kinds of people. Fey applauds her parents for not discriminating against her gay and otherwise “weirdo” (30) friends; she appreciates Larry Wentzler, the creator of Summer Showtime, for offering “a place where they belonged” (41) and weren’t treated differently. There is also, of course, the ubiquitous message of acceptance for women of all shapes, sizes, and faces, perhaps best encapsulated by her repetition of the statement “We should leave people alone about their weight” (106, 108) in her chapters about “being very very skinny” and “being a little bit fat.” Finally, she loves her show because, like so many “beloved shows like Cheers, Frasier, Seinfeld, Newhart, and The Dick Van Dyke Show,” it casts people with “normal human faces” as opposed to “every character being ‘hot’” (174). The popularity of these shows is further evidence that people should be treated with equal respect not despite, but because of, their differences.