Bossypants - The Beginning
It was quite a flutter when I came across 30 Rock in 2009. Shows with female professional leads set in NYC weren’t new to me; I loved and adored Just Shoot Me! and Caroline In The City. But this show was different. Liz Lemon was somehow so much more relatable, and very real. Like about a few thousand others, I too was instantly a fan of Tina Fey.
I bootlegged her memoir Bossypants when it came out in 2011, and read it cover to cover late at night instead of finishing my Introduction to Graphical Models homework. There was something so interesting and riveting about the book. It’s been nine years since then, but the audiobook is one of my top comfort-listens still.
For both the publishing world and me, that book opened up a whole world of Female Comedian Memoirs. It wasn’t long before I read Sarah Silverman’s The Bedwetter, Rachel Dratch’s Girl Walks Into A Bar, Amy Poehler’s Yes Please!, Mindy Kaling’s Is Everybody Hanging Out Without Me? and Why Not Me?, Lena Dunham’s Not That Kind Of Girl, Issa Rae’s The Misadventures of Awkward Black Girl and even Retta’s So Close To Being The Sh*t, Y’all Don’t Even Know. While not being a comedian, I’d also like to add Shonda Rimes’ The Year of Yes. And in the latest in that series, I just got done with Ali Wong’s Dear Girls.
As you can see, there’s a lot of these, and they qualify as their own genre.
The Female Comedian Memoir Formula
Like any genre, this one too has its tropes. It often involves an awkward childhood, an even more awkward college experience filled with bad dates, bad, inexperienced sex and some self-realizations, some stories of their early hustles in comedy starring some now-famous comedians, followed by the moneyshot, the tell-all section where you expect to hear all about the show they are most famous for, but you get mostly politically correct takes, and some (not so) strong opinions about being a woman in comedy. And then it tapers off into some filler material involving insecurities about appearance, being a mom, and generic advice about sex, drugs, sleeping with comedians (universal advice: Don’t), and maybe one hobby they want to be known for. It’s a decent recipe and scratches all the right itches.
The issue is, it only works if you ARE insecure about your appearance in a non-moviestar way, if you WERE awkward as a child/teen, or if you DID have actually awkward sex that you personally found awkward. Which was probably true for Sarah Silverman and Tina Fey, and somewhat for Amy Poehler, but everyone else, not so much. Yet, they persisted with this formula.
Mindy Kaling’s book’s very title strikes at that insecurity of being awkward. When I saw Is Everybody Hanging Out Without Me? I expected a trip of awkwardness and struggle. But no, she had friends. The title alludes to this incident when she was drifting apart from her group of childhood friends and instead spending more time with artsy kids, and ONCE she found that her old friends were having lunch without her. I felt scammed.
And Issa Rae might have been disturbed, or bullied, or even wounded, but she didn’t come across as awkward in the least.
The other thing is, there seemed to be a pretty steady, well-known pipeline to success for the younger comics. Tina Fey had funny stories of working at the Y and going on the road for Second City, Sarah Silverman was friends with homeless men who advertised for her shows and showed her where the knives were hidden in case things got bad, and Amy Poehler had some interesting stories of being in the Upright Citizens Brigade. But Mindy Kaling was in NYC for a hot minute before doing a two-woman sketch show with a friend, which got featured at Aspen. Issa Rae went to Stanford and had a web series. Lena Dunham is all downright unrelatable privilege with gobs of self-pity.
I find it hard to relate to most of these memoirs. I love all the shows, and I’m hungry for celebrity trivia. I also am very impressed by these women. But yet, something is missing.
Why does it work?
Celebrity memoirs are nothing new. Ellen has at least three, apparently. But they were Celebrity Memoirs. They were all extremely politically correct, didn’t slag on anyone, and weren’t raw. And more often than not, they were ghostwritten for actresses by someone who could actually write, and they portrayed their subject in nothing but the best possible light.
But Bossypants was written by an actress who was also a writer. And she was just like us, only more famous, rubbing shoulders with Presidential hopefuls. Tina Fey had this air about her where she related more with the small fry than with the people who holidayed at St Barth’s. Especially since she holidayed in Youngstown, OH, was open about all the guilt she felt, but not so much that you felt sad and awkward for her the way you do reading Rachel Dratch’s. She was one of us. She was our woman on the inside, our window to that world that we otherwise don’t have a hope of knowing about. She gossiped with us small fry about the big leagues, a move that is an instant win of hearts and minds.
All the tropes were authentic in her case. She did used to be heavy until she got on TV. She did find it hard to date in her teens. She simultaneously acknowledged she wasn’t a beauty contest winner while being quite comfortable with that fact and approached the topic with humor and confidence.
But more important is what she didn’t do.
She didn’t overstay her welcome. She only wrote about those bits that were interesting. There were maybe one and a half chapters that we could have done without (like the chapter with her replying to internet comments), but every bit was taut and dense with jokes and feelings.
She didn’t overdo the memoir bit. She didn’t write a bitter tell-all, and didn’t say anything scandalous that might have pitted her against anyone. And she managed this while still paying heed to how regular people felt about show business, with experiences about how she realized celebrities were still regular people who wanted to do a good job, and still bashing some common quirks of movie stars on SNL.
And most importantly, it was all her. All of it was on brand. She is this sarcastic, flawed, self-righteous woman who is serious about her work all through the memoir, even when she’s talking about confronting her own discomfort with her gay friends, or her struggles with parenting.
She crafted a template that was uniquely her. Someone without her background imitating it isn’t going to have as much success.
Similarly, Sarah Silverman also stays extremely on-brand. Her memoir isn’t for everyone, but if you like her comedy, you’ll like her book. Her stories are a lot more real and a lot more sad, especially her childhood struggles with depression. But it’s impossible for her to conform to anyone else’s template, and that completely makes her book her own and no one else’s.
When It Doesn’t Work
In contrast, Lena Dunham does make it uncomfortable with her now-infamous tale of her weird behavior with her sister. As does Issa Rae with her tales of catfishing people online as a teen, and serial cheating as an adult. It’s uncomfortable to read Mindy Kaling’s memoir where she tries to paint her unrequited romance with BJ Novak as a deep and meaningful friendship. I feel incredibly sorry for Rachel Dratch in some parts of her memoir where she admits to being unsuccessful, but she makes up for it by bringing in her positivity with her personal and spiritual life.
It takes a lot of skill to pick things to talk about from your personal life that are entertaining and raw, while still painting you as a flawed, but good person, and not everyone is canny about that.
Additionally, incredibly good-looking and well-dressed women talking about not wanting to conform to feminine standards for appearance is a huge turn-off. It’s like when you walk into an immaculate house and the host apologizes that everything is ‘such a mess’. It makes you feel bad about yourself. I simply couldn’t buy Amy Poehler or Issa Rae playing that angle.
Also, everyone has awkward sex when they are young. It’s not unique anymore. While Chelsea Handler tries to make a thing of that in a memoir titled My Horizontal Life - A Collection Of One Night Stands, I imagine it would get quite exhausting, and would go quite easily from “Haha, that’s a funny story” to “I’m worried for your mental health.” I don’t say this in a prudish way; it’s just not novel enough in today’s day and age, and if someone thinks it is, it seems like their self esteem is tied to that part of their identity in unhealthy ways. It’s interesting when it’s thrown in as part of a larger narrative on their life experiences, but it has to tie into something bigger in order for people to relate.
Also, you have got to gossip about the big leagues with the small fry. Most people don’t do that, choosing instead to attribute their success to hard work and dedication and maybe a godparent or two. They don’t rib bigger celebrities. They don’t spill tea about how the sausage is made. And they are just a little too desperate to get into the big leagues, or a little too happy to have got there.
Ali Wong’s Dear Girls, and A Possible New Template?
The first slew of comedian memoirs came when celebrities didn’t really use social media and weren’t all over Youtube giving speeches and interviews. They also weren’t putting out a comedy special a year, and the confessional, personal style of standup wasn’t as big a thing.
You knew them a little from their shows, and wondered what they were like in real life. You scoured interviews to learn as much as you could, because that’s all you’d get; most comedians and writers wouldn’t grace the blind items of gossip columns.
They also didn’t have a new embarrassment every month like Lena Dunham, so a book had sticking value as the only way you’d get deep into a celebrity’s life for years.
But Ali Wong doesn’t fit into those boxes. The standup special that shot her to fame had her talking about past miscarriages in a bandage dress that showed off her pregnant belly; I’m not sure how much more personal and vulnerable you can get. How much closer can a memoir get you?
She stays off most of her professional life other than a little about her beginnings in the comedy clubs of San Francisco. She makes it a completely personal memoir as a series of letters to her daughters. It’s heavy on family and other personal topics. She talks about her own adolescence as a wild child and how it limited her, and her family and her immigrant background.
There’s a whole bunch of pointless stories, like her foreign exchange trips and such from college, but they are on brand, as a letter from a parent to her children. There’s salacious, dirty stories, too, but also is her being completely on brand.
A celebrity memoir is supposed to raise your profile and make you more relatable and boost your brand. She manages to do that by sticking with the personal. It’s not good for business to talk about other comics, especially as a standup, so she doesn’t as much, apart from a few positive stories about other Asian-American comedians.
It seems that the definition of personal brand has changed. You’re a more niche quantity as a comic these days, and you usually don’t have a Seinfeld-level reach, unless you’re John Mulaney. You just play to that audience and maybe thoughts of winning over a new audience with your book isn’t really the point anymore. You aren’t really angling for an excerpt to be published in a big magazine or newspaper, given those are dying anyway and Netflix probably has more reach. You probably hope to make headlines for salacious details in your memoir, but not too much, because you don’t want to pit yourself on one side of any battle anymore.
The new memoir is a different beast in terms of its goals.
Female Comedian Memoirs Are Dead.
A book deal used to be a big deal. It no longer is. It’s getting harder and harder to market actual novels for publishing houses. It’s just easier to find a known quantity and have them put their name on something that has a readymade audience in their fan base.
They are getting much safer and much less entertaining. A memoir is part of your long-term PR strategy now, not just something you write only when you have something to say. It’s hard to be interesting anyway, when your path to success is through a pipeline that thousands of others pass through and have some level of success with.
Besides, any upcoming comedian now has a podcast anyway, where they interview their friends and share intimate details of their lives. I was interested and fascinated by Nicole Byer from her comedy and Nailed It!, but her podcast has a couple of hundred episodes, and after about 10 or 12, I got the general idea. She might probably put out her memoir sometime, probably titled I Eat Cake For A Living, And Other Tinder Taglines. Would I want to read it? Probably from a library, definitely not if I’ve to keep a copy on my Kindle or in my house.
This genre isn’t going to die, but it’s definitely not going to have the same function or impact. Personal brands are going to be more tightly defined, with smaller reaches, and memoirs as an extension of that will cater to a smaller audience that is already in the know about the topics discussed. Your personal brand is no longer just your work. It is an extension of you as a person.
People will still try to copy each other's formula, but there will be more of a variety of recipes, and people will come up with their own hybrids instead of sticking to a one-size-fits-all template.
That said, I don’t think I’ll care for them anymore. It’ll go back to being like every other celebrity memoir. Safe, boring, preaching to the choir. It also takes talent to get a variety of people to care about what you’re saying, and you’d think that would be something people are getting more practice with, given it’s harder to get heard. But instead, I’m seeing people come up in a safe scene of like-minded voices, and just stay there instead of branching out, or trying to cross over. That isn’t as easily marketable and that’s easy to confuse for unsuccessful/unliked.
It’s also a good thing that memoirs by women are no longer rare or unique. There’s so many of them that the market is basically flooded. It’s going to take a lot to be ‘fresh’ or ‘interesting’. Especially given how even the smallest person in show business is trying to cultivate a following, and followings of a 100k aren’t even considered big anymore. A celebrity is no longer inaccessible, and buying a book that’s about their life isn’t going to be as awaited as bated breath as it used to be.
I gotta say, I dislike Ali Wong.
I personally dislike her as a person, given her first chapter has a whole section on why it’s great to marry within your own race, and several disses on other races. While she tries to play it off as “White people, right?”, you can tell she thinks something mean about every race. She has quite openly dissed India with stereotypes and other garbage insults in her movie Always Be My Maybe, so I’m not surprised she holds such views.
Also she tries to joke about how she ‘trapped’ her husband, and changed his mind about eating meat and having kids. It doesn’t seem like it’s a joke. That’s incredibly depressing.
As an aside, anyone of any race who advocates only marrying within their own community has almost always turned out to be a close-minded bigot. The reasons are almost always things like food or language, but you can tell there’s a lot of negativity lying there unsaid which will lead into some sort of superiority.
Which also seems to be present in spades, with her attributing every positive quality to being an immigrant of a specific background. I’m also an immigrant who is proud of my heritage, but the more people I meet, the more I realize positive and negative qualities are present in every culture, and often it’s the same positive qualities across a wide swathe of cultures - frugality, family values, excellent food, focus and dedication, high standards, ambition, and sticking to what you believe. Heck, some of these qualities are part of Amazon’s Leadership Principles, so I don’t believe any one culture owns them; they are widespread enough to be corporatized. .
The second generation immigrant experience seems to have been incredibly different 40 years ago, which might have led to more closed-mindedness in order to preserve their heritage. But I think immigrant groups need to find a path out of this ‘difference anxiety’, which makes people react either with feelings of inferiority and complete subsuming of their culture with the host culture, or with feelings of superiority where they remain resistant to integration. Neither seems healthy. Conversations around culture need to start with the shared sense of humanity and proceed from there. That’s not where it’s at right now, but I’m hopeful that that is the direction where things are heading in the long run. Studying history makes me realize we were always an incredibly globalized world, and it comes to us naturally to be kind to each others’ differences.