How Whitney Cummings Learned to Write Roast Jokes

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Photo: Jeff Kravitz/FilmMagic

The following is an excerpt from Whitney Cummings’s new memoir, I’m Fine … and Other Lies, out October 3. You can catch her on tour this fall.

People always ask me how I got funny. The short answer is: I had to figure out a way to be liked. The long answer is more complicated because humor also developed as a survival mechanism to protect myself and disarm or intimidate people when I didn’t feel safe, to make fun of myself before other people could, to avoid having to feel sadness, or to mitigate the gravity of a situation because laughter was my anesthetic for pain. Also, my last name is Cummings, so as you can probably imagine, I had to learn to defend myself from insults pretty early on in life.

My parents were also very funny. My dad was a master of hyperbole and notorious for performing scenes from ¡Three Amigos! in public, much to my chagrin as a kid with low self-esteem. When he would pick me up from school, he would hide behind a car, and caw like a nasal bird, yelling, “Look up here! Look up here!” à la Steve Martin in the scene where he’s standing on the billboard. The later he picked me up, the louder his bird impressions were, always managing to make up for his lack of actual timing with impeccable comic timing.

My dad also had a very serious side, especially when it came to studying for tests. He’d drill me on spelling over and over, instilling a relentless work ethic and deep fear of failure in me. But every now and then, if I was nailing my vocabulary definitions or state capitals, he would look at the textbook I was memorizing from, bug his eyes out, and say, “You’re right, but how do we know this book is right?!” He would momentarily look super panicked, which caused me to have a complete freak-out that the textbook was wrong. Once he got me, he would crack up laughing. Then I would crack up laughing. This could have been very damaging to my psyche and ability to trust men, but in our family, laughs were way more important than mental health.

My dad’s all-time classic bit was at restaurants. After I had excused myself from the table to go to the restroom, he would dramatically shout “Hey!” Then when I’d turn back to the table, he’d wistfully announce, “I’ll wait here.” Again, this may not sound funny to you, but the fact that he did it so consistently and cracked himself up made it a timeless classic for us. My dad showed me that it’s my responsibility to provide my own joy, and that every moment is a chance to find lightness.

My whole family had jokes like this, using humor to make us all think things were fine when they were far from it. Nebulous work situations, failed marriages, and financial uncertainty were constantly joked about. Some people take pills, some people drink, some people gamble—my family cracked jokes to make the pain go away. I’m sure some of them probably also took pills and drank, but that’s another chapter I’ll write after I’ve had a couple of pills and some drinks.

My mom’s brand of humor was more of the Ab Fab slapstick genre. She’s blond and beautiful, and always dressed very stylishly, so this wasn’t a huge reach, given that she was always juggling way too many bags, balancing a coffee cup, and frantically looking for her glasses when there were two pairs on her head. I vividly remember as a kid getting stuck in a parking lot because my mom had lost the ticket. She bribed the parking attendant with whatever she could find in the car. Vogue magazine? A kid’s thermos? Panicked and bombing, she snatched the bag of peanut butter crackers out of my hand and tried to make them appealing to the Hispanic parking attendant, who I can only guess was being given more ammunition to resent white people. It was humiliating at the time, but in retrospect, I can appreciate how hilarious it was that she was bartering with trash from her car in order to absolve us of a parking fee.

Everyone in my family loved to laugh. Looking back, I now realize they needed to laugh. Loud laughter was how we all said “We’re fine!” even though in my gut, I didn’t feel like anything was fine. Laughter’s the universal sign for “Everything’s cool! Let’s keep it light!” The tenser things got, the more we laughed. My family also used passive-aggressive jokes to communicate what we couldn’t say honestly. Conversations at our holiday gatherings were peppered with insults wrapped in jokes of the “I don’t care that we had to sell the house to pay for Marcy’s divorce! We hated that house anyway!” variety. These way-too-close-to-home backhanded “jokes” were always followed by uproarious laughter. It was around then that my brain’s wiring was custom-designed; I learned never to tell anyone how you really feel and not to take people at face value. Kids, do not try this at home. Later in life this mentality morphs into a sort of emotional dyslexia. In my case, my brain always got things backward: When someone was nice to me, I’d get suspicious and wonder what their motives were, assuming they were trying either to manipulate me or to recruit me into a cult. And if people were mean to me, I’d immediately fall in love with them.

Since we communicated in loaded jabs, nobody was safe from a Cummings family roast. I remember being the target of ridicule at eight years old, around the time I became notorious for having a perpetual case of head lice. (What can I say? My scalp is delicious.) After I was sent home from school for the fifth time, my parents’ only option was to cut my hair as short as possible so the lice were more easily exterminated by whatever Rite Aid poison was being marketed as lice shampoo. This resulted in a terrible bowl cut à la Jim Carrey’s character in Dumb and Dumber. I was lambasted by my family for months for looking like Moe from the Three Stooges, a Shetland pony, and a wet poodle, in addition to some probably racist Polish jokes I was too young to understand.

I’m sure most kids would have been embarrassed or cried, which is of course the healthy reaction, but I learned pretty quickly that the best tactic was to just go numb and laugh along with them. That’s the American way, right? Be strong, man up, pretend to not have feelings if you aren’t lucky enough to be a psychopath. I developed the survival skill of giggling when I was uncomfortable. You should see me at the gyno; it’s a goddamn laugh riot.

To avoid getting hurt or being vulnerable, my brain hatched the perfect plan: When people make fun of you, laugh. When people hurt you, laugh. When you feel unsafe, laugh. It tricks everyone into thinking you don’t care, which is the best defense. One day when my family was ripping on my hair, I started making fun of it as well. I figured out that if you just make fun of yourself first, you can beat people to the punch. And if you can’t beat them to the punch, just punch yourself. Anything for a laugh.

Of course we shouldn’t take ourselves too seriously, but there’s a difference between having a healthy perspective and emotional self-flagellation. For the first thirty years of my life, self-deprecation was my main approach, although I now feel that a little piece of you dies every time you put yourself down. Even as a joke. Seemingly meaningless quips like “God, I’m such an idiot” or “Of course I forgot my keys, I’m such a mess” are death by a thousand cuts to your soul. If anyone spoke to me the way I used to speak to myself, I would file a restraining order. Why am I so nice to complete strangers, who could be sociopathic murderers or felons, but when it comes to myself, someone I know is not a murderer or a felon, I’m Ike Turner. I’m sure there’s a fresher domestic violence reference than Ike Turner, but I feel like he’s oddly evergreen. His assholery really is timelessly classic. He’s like the Audrey Hepburn of emotionally abusive dickheads.

Once I was in therapy with Vera, and per usual, I had done something self-defeating and inane as a result of my lack of self-awareness and self-respect. As I recounted the mistake, I kept saying, “I know, I’m a moron.”

She got silent. Things got awkward and she genuinely asked, “Why would you say that about yourself?”

I thought hard about the question, wanting to come up with the perfect answer that would impress Vera and justify my habitual mindless behavior. Finally I came up with what I thought was an incredibly incisive and true answer: “I’m a comedian and being negative about myself is a comedian thing. Self-deprecating is funny.” The only issue with my brilliant answer about how funny it was was that Vera was not laughing.

“It’s actually not funny,” she said.

The fact that Vera said this was literally shocking, which is in itself shocking, given whenever I’ve said “I’m an idiot,” nobody has ever laughed. I should not have needed a professional to explain that an absence of laughter indicates when something’s un-funny, but I guess my negative, fictitious inner monologue was too loud for me to even hear what was going on in real time. Now that I’m mentally awake, I can see that being negative about yourself actually makes people not only not laugh, but get uncomfortable. It really weirds out the vibe. When we’re mean to ourselves, the people around us don’t know whether they’re supposed to agree, disagree, argue, or call a suicide hotline. Sarah Silverman has the most perfect response to people being self-deprecating. When someone says something like “I’m so dumb,” she says, “Hey, don’t talk about my friend like that.”

Sometime in 2007, while self-deprecation wasn’t working out particularly well for me, the ability to write hard-core roast jokes was. I was watching the Comedy Central roast of William Shatner, and after each setup, I was able to guess the punch lines, often predicting the exact ones that were said. I realized I had a somewhat unsettling knack for writing incredibly brutal jokes. I also realized my rent had been late for five years, so I asked my manager if I could apply to be a roast-joke writer for Comedy Central. He emailed me back saying the same five guys had written for the roasts since they started and that they generally don’t take on new writers. So, no. Oddly motivated by the rejection, I decided I’d just have to prove myself. I refused to take no for an answer and I wrote eighteen pages of jokes for the impending roast, which was for the great who-knows-what-he-actually-does-for-a-living Flavor Flav. If you know anything about him, you know that coming up with premises for insulting him isn’t rocket science, but I banged out as many as I could. I begged my manager to send them in.

From what I was told, the joke that got me the job was: “Flavor Flav, you look like what Magic Johnson should look like right now.” So much for good karma.

Working for the roasts was my literal dream job. I loved being in the roast writers room, where sharp comedy writers sat around all day eatin’ crap and talkin’ shit. We threw around insults all day, pertaining to the talent on the show, but also to each other. Maybe I felt so at home because I was able to recreate my childhood circumstances of dodging emotional bullets and using caustic humor to avoid intimacy. It also distracted me from my inner monologue, which heckled me with even worse insults than we wrote for Flavor Flav.

Eventually I became one of the go-to people for roast jokes, which I now realize is something of a dubious honor. But Mommy had bills to pay, and it was better than getting paid forty bucks for doing focus group tests in which I would take pills that had not yet been approved by the FDA and probably never would be approved by the FDA.

Adapted from I’M FINE … AND OTHER LIES by Whitney Cummings, to be published on October 3, 2017, by G. P. Putnam’s Sons, an imprint of Penguin Publishing Group, a division of Penguin Random House, LLC. Copyright © 2017 by Whitney Cummings.

How Whitney Cummings Learned to Write Roast Jokes