Who Gets To Be Bossypants? On Class and Privilege in Female Comedians’ Memoirs

This past April marked ten years since the publication of Tina Fey’s Bossypants, the first in a bestselling genre of the past decade: the Comedic Actress Memoir. In 2011, Bitch Media noted that Bossypants, which came out while 30 Rock was still on the air, was unusual: memoirs of women comedians had previously either been published posthumously (Lucille Ball’s and Gilda Radner’s) or by women at the very end of their careers (Phyllis Diller published hers at the age of 88). Bitch referred to women publishing memoirs “while their careers have, for the most part, just started to peak” as “the newest microtrend in memoir.”

Mindy Kaling is the most prolific contributor to the genre—Is Everyone Hanging Out Without Me?, the first of her three books, came out six months after Fey’s book. Those two were followed by, among others, Rachel Dratch’s Girl Walks into a Bar . . . (2013), Amy Poehler’s Yes Please (2014), Lena Dunham’s Not that Kind of Girl (2014), Issa Rae’s The Misadventures of Awkward Black Girl (2016), Amy Schumer’s Girl with the Lower Back Tattoo (2016), Tiffany Haddish’s The Last Black Unicorn (2017) and Ellie Kemper’s My Squirrel Days (2018). They sell very well, mostly to women: noting that Poehler, Dunham, and Fey sold a nearly identical number of books their first week, The Cut asked, “Did the Same 38,000 Women Buy These Books?” A memoir or essay collection is now simply expected once you’re famous enough to head a TV show; a fact that the opening sentence of Kemper’s memoir takes as a given (“There comes a time in every sitcom actress’s life when she is faced with the prospect of writing a book”).

The Comedic Actress memoirs all share the same structure: the actress explains at length how she is the least likely person to whom success would come, via anecdotes showing that she is Not Cool and instead Fatally Awkward. As a teenager, Fey describes herself as “hairy and sweaty,” Dunham as “covered in a thick layer of grease.” Their early forays into show business also don’t go well: at her audition for Saturday Night Live, Kemper tells the receptionist that she is there to see “Michael Lornes”; Kaling, not a dancer, goes to a musical theater audition dressed like “a children’s birthday party performer playing Angelina Ballerina.” Despite putting her foot in her mouth and generally being a goofball, the memoirist is able to out-work and out-hustle everyone else to make her dreams come true.

Every woman on the aforementioned list did work very hard for her success; every one of them is extremely talented. Trying to make a living as an actor at all is a long shot; a woman achieving success in the notorious boys’ club of comedy is a longer shot still.

But “hard work” or even “good luck” is rarely the whole story. Earlier this summer, Twitter’s spotlight swiveled, rather randomly, to land on one Comedic Actress memoirist, Ellie Kemper, who is best known for portraying awkward people on The Office and Unbreakable Kimmy Schmidt. At age 19, Kemper had been crowned pageant queen at a debutante ball put on by the Veiled Prophet Organization, a St. Louis-based social club for the high-society elites that had a history of intimidating and excluding Black residents; one Missouri woman tweeted that the organization was “our local KKK.” While that was not technically true, the “Veiled Prophet” wears a white hood and white robes that look awfully Klan-ish; Kemper’s Wikipedia page was briefly edited to state that her occupation was “KKK Princess.”

The Twitter reckoning also involved many of her fans learning of the extent of Kemper’s wealth (her family is one of the wealthiest in the state of Missouri; three local art museums bear their family’s name). Her nearly 300-page memoir does not mention the pageant, and gives little indication that she is anything other than “middle class”; specifically, from what Anne Helen Petersen calls “the vast middle, the typical, the median, the democratic “we” . . . a place in the American imaginary . . . overwritten with narratives of bootstrapping, hard work, and meritocracy.”

It was, of course, Kemper’s prerogative to leave out both the pageant and discussions of her family’s money in her book; there is no such thing as a “tell-all” memoir, and she also never claimed to be writing one. In her book’s introduction, she recounts writing advice that she received to “write like your parents are dead . . . [f]ree yourself from any harnesses or constraints that are keeping you from telling your truth” and retorts that she instead wanted to “write like they are alive, thriving, and peering over my shoulder.”

If you’re looking for them, there are also plenty of clues in the book that she would only be “the girl next door” if you lived in a gated community: the anecdote involving a squirrel, from which the book’s title is drawn, only makes sense in a backyard measured in acres, not feet. The book recounts how she attended Princeton and Oxford, then pursued comedy in Chicago, then New York, all of which, she acknowledges, was possibly because she was “in the rare position of being able to reach out to my parents for money if I needed it.” But the details are hazy. The book is almost entirely free of any discussions of class or race, and how being both rich and white might have made her path to stardom an easier one.

This is not an issue unique to Kemper’s book, or to Kemper herself. The memoirs by all the actresses follow an unsurprising pattern: the more money the actress’s family has, the less she talks about money.

I am also a white woman from a well-off family (not Kemper money, I hasten to add, as if that really matters—you either have student loans, or you don’t, and I don’t). Until the past few years, I had thought very little about how those things undergird every choice I’ve made in my life: the places I can live, the risks I can take, the ways I can spend my time (re-reading memoirs by actresses, for one), the non-lucrative careers I can pursue (freelance writing). It shapes everything about my life, but has often been invisible to me.

When you don’t have to think about money, it’s very easy to not think very much about money. And “rich” is always what someone else is: Poehler, Fey, and Kemper’s books all include a character of an unnamed Rich Person. In Fey’s book, there is a “rich old guy” who demands, “Do you know who I am?” In Poehler’s, she yells at a (presumably different) rich guy, “Who do you think you are?” Kemper’s includes a rich woman who tries to pay her improv troupe in hors d’oeuvres rather than money. Rich people are arrogant, out of touch, and greedy—nothing like the relatable narrator.

The same pattern holds when looking at the way the books discuss race: except for Tina Fey, whose book has a truly jaw-dropping number of racist jokes, the white actresses write very little about race; the women of color write about it a lot, and much more frankly. For example, Amy Poehler writes that her high school “had a quiet hum of racism and homophobia”: a hum which, I’d guess, was not nearly as quiet for those who weren’t white and straight. Both Tiffany Haddish and Issae Rae went to predominantly white schools, where awareness of their visible different-ness was unavoidable: Haddish writes in The Last Black Unicorn that her high school was “3 percent [B]lack… and pretty much all of them were rich”; Rae describes a substitute teacher calling roll and “pretending to look through the sea of white kids to find my ethnic ass.”

Kaling’s Why Not Me? includes a paragraph where she muses about what her freshman year at Dartmouth would have been like had she been born a white man. (She concludes she would have died of alcohol poisoning and that she was thus lucky to have been born a “socially anxious Indian woman.”) The absence of race in the white women’s memoirs isn’t surprising either: white people are rarely asked to think about how their race, and even the titles reflect a society which still assumes whiteness as a default. Dratch, Dunham, and Schumer can just be “girls”; Issa Rae is a “Black girl.”

Tiffany Haddish is the only one of the aforementioned comedians who grew up in acute poverty, and her memoir makes it easy to see why there are a lot more actors (and other artists) with backgrounds that resemble Kemper’s than resemble Haddish’s. When Haddish gets her first big break (a local news story about her time at comedy camp), she is in foster care and has no legal guardian; she has to take the bus to the courthouse and appear before a judge in order to have him sign the consent forms that will let her appear on television. The next year, she gets into NYU but has no way to pay for it and isn’t offered financial aid; she attends community college and tries to do comedy in LA but quickly discovers that she cannot “find time to go to college, and work, then also take a bus to do comedy” for shows that, at the time, pay her $10-15 each. Those are two of the more mild challenges she encounters—her story includes domestic violence, sexual abuse, and homelessness. And while, improbably, it ends with stardom and a friendship with Will Smith, it’s not hard to see why most stories like hers do not.

These books, of course, are not supposed to be Deep Meditations on Race and Class. They are supposed to, first and foremost, be funny. They are also supposed to raise an actor’s profile, and cash in on their existing brand. There are beats of real emotion in all of the books, but a jarring convention of the genre is the tonal similarity between the books: everything in them is a joke, or the setup to a joke. Kemper talking about sending back a brunch order of lentil and quinoa (bafflingly, an anecdote that consumes an entire eleven-page chapter) has the same “what was I thinking?” tone as Haddish does when talking about how, when she was 13, she thought that enduring sexual abuse from a foster parent would make her breasts grow bigger. Immediately after the book was released in 2018, Vogue suggested that Kemper’s lighter-than-air apolitical comedy felt “a little misplaced”; her book today feels like a relic of a completely different time. How comedy co-exists with climate change and a pandemic, and the idea that one can “heal the world with comedy” is both parodied and explored by Bo Burnham in his special Inside (nearly universally adored, despite being only intermittently funny).

The critique of these books fit into the broader conversation around the shallowness of the narrative that “hard work” and “talent” are the only ingredients at play in determining who makes it big and who doesn’t; likewise, the false idea that a white person must be either a “KKK princess” or an avowed white supremacist to benefit from white supremacy. And as awkward or unattractive as many of the women on the list may believe themselves to be, or may have felt, they were not all outsiders in the same way. In a telling passage in Fey’s book, she seems to briefly consider that possibility. After relaying an anecdote where she essentially steals a job from a woman who really needed it, she adds “That makes me sound like a jerk, I know. But remember the beginning of the story where I was the underdog? No? Me neither.”