The Much Rewarded Cruelty of David Sedaris

Syd Graves
7 min readFeb 21, 2021
Watson Lake Arizona ~ photo credit: Cindi

Exploring Amy and David Sedaris’ writings for inspiration as I delve into my own family toxicity, it turns out they’re from a deeply fucked up family just like me. Well, not at all like me but fucked up and damaged we have in common.

David has spun his dysfunction into wealth, crafting just the right dose of self effacing barbs to escape the truth that he’s just a mean asshole who tied rocks to his siblings then threw them in a lake and tried to drown them.

Amy has spun hers into scathing critique of being a woman in this shithole culture and in a normal plot twist, has been less embraced by this shithole culture than David’s cruelty. But hey that’s why this is a shithole culture. Amy is infinitely more talented than David, it’s just that being a man put him closer to the finish line in this “I worked hard for this wealth” myth of a life game from the day he slid out of his mom’s vag compared to Amy having to literally work hard for her place in entertainment.

It’s an interesting observation to notice how Amy’s comedy has been received compared to David’s. You might say there isn’t a comparison. But there is. David has made a more than comfortable living being cruel and is described as delivering dark humor. Amy is described as having idiosyncratic humor. They both poke at the damage a family can wreak on a child and in another normal cultural plot twist, David attacks everyone while Amy attacks the essence of what this fucked up cultures demands of womanhood. On the surface her focus appears to be of a particular encapsulated moment in time, maybe of her mother’s time. But watch enough of her work and you’ll see she’s putting a magnifying glass on how today’s culture is still a dick to women.

David gets to be cruel because no one fact checks him. Well, Tiffany did but…

There’s a story David tells about being in first class on a flight and he tells a woman who is not in first class how she isn’t counted as a human. I suppose it’s funny initially, but once you chew it a bit, the taste is fucking nasty. He takes liberties with everything and he gets away with it. He’s a white man so of course he does. It’s particularly sad to read his cutting words about his sister Tiffany when you know he is an addict too. An alcoholic. A druggie. A dirty grifter himself for years. But handling her pain isn’t as hard as handling his so Tiffany got the shaft, like his comments about the Elan school, something he barely touches on or probably worse tosses it off like it should not have been a deeply scaring wound in her life. Not a fucking person in her family had the compassion to talk to her about it or get her help after suffering there. I mean, David, for fuck’s sake have you bothered to watch The Last Stop?

Of course bullies have their own demons and maybe someone should have noticed David’s flair for the socio/psychopath’s path when he was a child tying rocks to siblings and tossing them in the water, acts he’s described and used to make a nice profit. That kind of shit should have gotten him sent to Elan instead of Tiffany, but Tiffany was the out of control girl. Boys are rarely seen as needing to be sedated to be controlled, if anything their fucked up behavior and treatment of others is given pass after pass after pass *cough, Brett Kavanaugh, Don The Con, Brock Turner, cough*. But guess who David’s demons didn’t matter to? His targets. They are simply at his disposal for content.

It’s as likely David is running as far away from the truth of his own life as it probably was that Tiffany wanted to escape the truth of hers. His treasured writings are of a humorously dysfunctional family we can all relate to. I wonder if the ways he describes her in the Guardian article are clues to how he is as a friend, brother, partner. I suspect they are:

At the time of her death, they had not spoken for several years. The last time he saw her was at the Symphony Hall in Boston, when he was on the verge of performing at the beginning of a tour. “‘David. David. It’s me. Your sister. I have something for you.’ And there was a guard holding the door open. And I said, ‘Could you close the door, please?’ And he shut the door in her face and I never saw her again.” He explains now that he knew that if he had spoken to her, it would have consumed him, and he would have lain awake every night thinking about it. “Every encounter with her was like that; everything was so deeply upsetting on so many levels. You had to block time for her.”

I wonder if there are people in David’s life that block time to suffer him or if his words laid on their shoulders consume them. It probably doesn’t matter to him.

Then there’s the time he made his audience pay him cash (quoted from the same Guardian article):

On one tour, he turned the tables on fans, however. His ATM card stopped working and so he decided to simply ask audiences for money. He’d tell them it was not a loan, nor for charity, and often walk out of a bookshop carrying $350 in donations. “But if there was a beggar outside, they wouldn’t have given him anything. It’s funny to give money to someone who doesn’t need it. Here’s $20, isn’t that funny? And I’m like, yeah, it is, and I would take the money.” Sometimes, he would spot someone who looked like they needed a hand, and give a chunk of it to them.

Maybe he simply stole money from them because of course it’s very funny when he retells the bit but not at all when his sister needed his help. Just like the time he let his audience believe he and Hugh weren’t together anymore, stretching the stinky bit long enough through his own fake tears to allow his audience to be brought to tears. What the fuck?

I wonder if he cares that his humor, his success, his money making is something he’s happy to let others pay the cost of, but not himself. When he published his diary entries, one describes Tiffany’s ectopic pregnancy and surgery to remove it:

Recently, he has read that essay aloud and has not had the response he expected, or at least had hoped for. “I thought that was the funniest thing in the world. The audience never laughs.” Perhaps, I suggest, this is because we have strong feelings about how traumatic such an event might be. “But it’s not like she wanted the baby,” he replies. Again, a directness that almost verges on the taboo, and has on occasion led to charges of insensitivity.

“But it’s not like she wanted the baby” — is this license?

David’s comments that he and his siblings should have said something to their mother but never did, about how Tiffany was treated — he pushes it all off onto his mom but in truth those types of behaviors get infected into a family. David’s dad was responsible for being cruel to Tiffany and who knows where that cruelty started toward her but there is no doubt Tiffany felt outside of her family, I mean her dad had to have been in agreement on sending her to Elan. In adulthood David and his siblings were responsible for being cruel to Tiffany. It’s the way generational cruelty gets passed down. It seems invisible. It seems like there is only one person in the family responsible for being cruel to Tiffany. David passes his mother’s and father’s cruelties on in his writing. He mentions how Tiffany felt everyone was “uniformly terrible to her”. From his writing it sounds like they were. There is no writing about how her family rallied around her to help her get help. Only how her family let her spiral away from them. His notes suggest medication is what stood between her and mental health. Maybe it was that her family couldn’t find a space for her pain in their world so she was the target of everyone in some form or another.

I’ve heard David of course, his voice instantly recognizable as one of the sweetheart voices of NPR—NPR by the way has a type; Ira, David, Guy, Mo. Go listen,they’re virtually indistinguishable.

In my exploration to find inspirational nuggets to teach me how to write about my own toxic family, there were criticisms of David on the piece he wrote after his sister Tiffany died by suicide. I’d read Now We Are Five before but re read it with eyes that might have been Tiffany’s. Then I dove deeper into several articles written by other people that included her as a human not a commodity, which David chooses to ignore, and it gave me an insight into how Tiffany didn’t like David writing about her — and how interesting it is he doesn’t give a fuck about her not wanting him to write about her.

David gets to write David’s world. Amy creates Amy’s world. I’ll do the same and expect to have someone complaining about how mean my words are about them as I write from one of my future three homes on different continents bought by my mean words some day. Just like David has.

Fingers crossed.

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Syd Graves

Not portraying this world better than it is. If you’re alive, you’re political. Opinion. IG @itisgrave & Twitter @itisgrave Syd is my pseud here.