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David Sedaris has produced a new book of essays roughly every three years for the last three decades.DREW GURIAN/Courtesy of MasterClass

Since his star-making debut on This American Life in the early 1990s, David Sedaris has produced a new book of essays roughly every three years for the past three decades, each one as dependably hilarious, bizarre and unexpectedly poignant as the last. After mining the fertile ground of his eccentric upbringing and years spent as a struggling, drug-addicted artist, Sedaris, now in his mid-60s, continues to share his trademark mix of observational humour and pathos in Happy-Go-Lucky, his ninth essay collection.

Sedaris’s new collection picks up roughly where the last one left off, featuring his usual cast of supporting characters including his boyfriend, Hugh, his siblings (among them actor and comedian Amy Sedaris) and a charmingly foul-mouthed cameo by the late Phyllis Diller. In it, he travels to Bucharest in search of flea markets, visits a gun range, feeds candy to ants and delves deeper than ever into his difficult relationship with his nonagenarian father. Basically, it’s everything you’d expect. And delightfully so.

Has the pandemic changed touring for you?

It feels like the America that I am moving through now is very different than the one that I was in before the pandemic. The rules are so different in one state to the next, in a red state and a blue state. Like, I was in California a few days ago and everybody in the store had a mask on, and everyone who worked in the store had a mask on, and I thought they were going to ask me to wear a mask – but I was kind of glad they didn’t because I got braces during the pandemic and I wanted people to see my teeth.

But then I went to Alabama where nobody in the state has a mask on. The problem is that masks have become a campaign button, so you can see somebody from a distance and tell how they voted, and I don’t think that that’s always a good thing. I think it can be good to meet people and talk to them and then maybe find out that they have different beliefs than you, rather than being able to tell it from a distance, and making up your mind about them before you even get a chance to know them.

Congratulations on getting your teeth fixed. Do you find moving through the world with perfect teeth changes things for you?

All I ever wanted was unremarkable teeth. I used to cover my mouth when I would talk to people and I would never smile in pictures, so it’s just been such a great feeling to let all that go. I didn’t realize how much time I spent thinking about it until I never thought about it any more.

Phyllis Diller makes an appearance in the book. How did you strike up that friendship?

I was doing a show in Los Angeles and she sent word wondering if I would like to get together. We met at the Bel Air hotel for lunch, and we just hit it off. She was really cool. Normally I don’t like to hear people’s ideas about comedy, but I loved hearing her talk about how she engaged with people. She used to have a wooden cigarette in a cigarette holder that she’d use as a baton, to start and stop the audience. It was fascinating.

Who’s the most famous person you’re friends with now?

Maybe my sister Amy. My best friend is still my best friend from when we met on my first day of college, and my second best friend is still my second best friend from when we met in college. But when you go over to Amy’s house, there’s no telling who you’ll find. She’s, you know, in that world so she can be really relaxed in front of those people. Whereas if you told me that we were going to be joined in five minutes by somebody who had done a shampoo commercial in 2007 I would just freeze.

You talk a lot more about your dad in this book, particularly some allegations of abuse your late sister Tiffany made against him, and a few traumatic incidents from your own childhood. Why did you wait until after he died to share these?

I think it would have pained him if I wrote the story while he was alive. I don’t believe that my dad did anything to my sister, but that said, the definition of abuse is changing so rapidly. Like, I never thought of myself as being abused, but if a parent treated their son the way my father treated me today, he would definitely be thought of as abusive. But back then, you know, everybody hit their kids and everybody said horrible things to their kids.

Even so, you certainly don’t paint him in a flattering light.

I thought for the essay to work, I had to add some of the other stuff that my dad did, like asking my sister Lisa to pose topless in the woods, and telling my sister Gretchen that she looked like an old whore. They didn’t help his case any, but being a creep doesn’t mean you’re a pedophile. So I thought it was important to add that stuff to the essay because it left the reader where my sisters and I are, going back and forth. I wanted to write an essay about what that does to a family.

Has your father’s death made you think more about what you want your funeral to be like?

It’s interesting because it used to be that the church was the centre of everybody’s life, and when somebody died, the church just kind of took over. But now, I don’t know. Do people put it on Facebook or something? Where would I hold a memorial service? What kind of a thing would it be when people get up and speak? I think I’d just hire someone – there must be people who specialize in that, right? Like death doulas?

If there aren’t there should be. Or you could rent out a Comme des Garçons store and have the service there …

I’ve got the perfect outfit, as long as I can still fit into it. I was going to wear it to my dad’s funeral, but it was really hot. It’s a black Comme des Garçons sport coat, but it’s interrupted just below the rib cage for, like, three inches with what looks like the curtains of a hearse, and then there are layers of black ruffles spilling from the hem. It’s fantastic. And it weighs a ton. My knees buckle when I put it on. The only problem I’m having is finding trousers to go with it, but hopefully I’ve got a while to figure that out.

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