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Pop culture obsessives writing for the pop culture obsessed.
Main image: Mike Rosenthal. Background images: screenshots of Black Monday (left) and Happy Endings (right)

Casey Wilson on her new book, her favorite Happy Endings moments, and what she learned from SNL

Main image: Mike Rosenthal. Background images: screenshots of Black Monday (left) and Happy Endings (right)
Graphic: Natalie Peeples

Casey Wilson will forever be known to many as Penny Hartz from dearly departed ABC sitcom Happy Endings. But since that show’s debut 10 years ago (and cancellation in 2013), Wilson’s career has expanded with a variety of projects. She’s currently starring in Black Monday, the Showtime comedy series about the 1987 stock market crash, which is produced by her husband, David Caspe. On the podcast front, she’s about to release The Shrink Next Door, and recently returned to the long-running Bitch Sesh, where she and actor Danielle Schneider discuss reality shows.

Illustration for article titled Casey Wilson on her new book, her favorite Happy Endings moments, and what she learned from SNL
Image: HarperCollins

But Wilson’s most personal new project is probably her recently published collection of essays: The Wreckage Of My Presence (May 4). In it, she covers everything from her love of lying down, to her inability to get her husband to return her phone calls, to a terrifying chapter about her son’s battle with celiac disease. Even when a subject is sad, as when Wilson discusses dealing with Mother’s Day after the death of her own mother, she brings a welcome and warm dose of humor to these all-too-relatable problems. The A.V. Club spoke to Wilson about her new book, her current favorite Housewives, and her most treasured moments from the still beloved Happy Endings.

The A.V. Club: In the first piece, “Bed Person,” your husband tells people “that if I could I’d walk around with two mattresses strapped to my front and back so I could flop down at any moment. He’s not wrong.” What was the impetus of having that be your lead-off?

Casey Wilson: It’s so funny, because I started the book about three, four years ago and have just been working on other stuff, and I had a different opener, which was called “Please Like Me.” And I kept pushing [the book], and by the time we were publishing the book I was 40. I don’t really feel like that anymore. I don’t feel as desperate for people to love this book as much as I would want them to do. I felt like more like an update after your thirties. I thought it conveyed my personality. A mix of ambition and laziness, but I haven’t quite seen that combo.

AVC: There’s also the chapter about dealing with your older son’s celiac disease. Was that hard to write about, or did you find it therapeutic after all you guys had gone through?

CW: It was definitely the hardest one to write about—should I even write about it? But I had half of it as an essay in The New York Times. And by then I’ve gotten into the full extent of what had happened. Just that one day I felt like only part of the story. And so I wrote it really quick and I was like, “I’m never reading that back again ever.”

AVC: It’s one of those things that many moms do: We internalize. You always feel with everything they’re going through, somehow, there’s something more we could have done.  

CW: Earlier today, I was of course, watching Real Housewives, because I genuinely have to for my job, right? But there I was watching the Atlanta reunion, and there’s this new housewife Drew. I don’t even know if it will make any sense, but normally you’re not that emotional watching the show. You’re laughing, you’re like, “This is crazy.” But she was very upset that Kenya Moore had retweeted something nasty about her mothering and she was so upset. And as I’m watching, I realized I was hysterical, crying like it was so unacceptable what Kenya did. Like, the mothering piece of guilt, and then to have someone else judge your mothering is so unacceptable and heartbreaking. And I was like, “Oh, my god, I don’t know if I’m too involved in these shows or…” I was putting myself in her shoes like she was trying to do the best thing she could in a situation and then saying everybody felt like she was a bad mom. I was like, “I don’t even know if I can watch this anymore.” I felt so badly for her. And she’s clearly such a great mom. That’s the irony of all of this.

AVC: Speaking of the Housewives, you’re back on Bitch Sesh. What are your main shows right now that you’re watching? Do you have favorites? You guys really liked Southern Comfort for a while.

CW: We do, but I had to scale back. This was my whole life. I have five. So that’s kind of what I do. I’ve always [been] tangentially involved in the Kardashians, but just as a fan and not as a reporter. Right now we’re all Housewives all the time. We’ve got Atlanta, we’ve got Dallas, we’ve got Jersey going. We’re waiting for New York. I’m glad that my book is coming out on the day of the New York premiere. Oh, my gosh. As I just talked to you, I got into the wrong car to pick up my son. It never ends.

AVC: I have a theory about the Housewives: I need a true north to hang on to. For me, it was Beverly Hills’ Lisa Vanderpump, because at least in the midst of all the mania, she would be kind of stable. But New York doesn’t seem to have that, but maybe that’s part of the fun and maybe I’m just missing it?

CW: Have you watched last season? I feel we’ve really gotten our true north in Leah, the new cast member. She’s so fun. She’s normal. She’s cool. Everybody loves her. Well, she throws tiki torches around in a naked, drunken moment.

AVC: Who doesn’t?

CW: Who doesn’t. And she’s still really fun, genuinely relatable. I agree with you, and I feel like we’ve been given a lot of balance with Leah. So she’s like the straight man in a way, looking around at everyone, like, “Am I like dreaming? What am I seeing here?”

AVC: Living where you do, do you ever meet these people in real life at events? Are you ever surprised by their real-life personas?

CW: I haven’t met that many of them, and I try not to. But I actually just did a show. I just finished, and Lisa Rinna also filmed on the day of it, and I didn’t even really go up to her. I said a quick hi and walked away. Because I am the type of person… if I get in too deep, I’ll never be able to speak freely about them as god intended. I met Kenya [from Real Housewives Of Atlanta] once and, honestly, I had such a nice time that I love her. So I find it hard to be [objective], having met her in real life, and I know I have blind spots for them after meeting them.

AVC: It’s also the 10th anniversary of the debut of Happy Endings this year.

CW: I can’t believe that it’s been 10 years. I’m also always so blown away by the generosity of the fans and how much they love the show and continue to love it. And people have found it on Hulu and HBO Max. It’s really cool. Especially during the pandemic, I think a lot of people found it or returned to it because it has funny jokes and warmth, and I think we’re all craving that.

AVC: What are your favorite Happy Endings episodes or the ones that first come to mind?

CW: I remember “Cocktails And Dreams,” when I did the monologue about the whore’s bath. That was my most fun thing. I loved the episode with Megan Mullally where I got to dance to “Torn.” I love the episode where Damon [Wayans Jr.] is going to the dentist and he does that hilariously comic entrance into the office. I love the Halloween episode with [Adam] Pally, the Baby Bjorn episode. And I also love one where Pally thinks he won the lottery and we’re pranking him, and his reaction to that, it was so funny. His anger, it was so real. When he says, “I will get back at all of you”–something like that, “You will pay for that.” I’ve never felt more real acting onscreen.

You know what, I have to say, because I’m on this show Black Monday on Showtime, with Don Cheadle and Regina Hall, and we were watching a part of the first episode last night, I watched it, and it’s season three. And it hasn’t really found a huge audience. It is just as funny, if not funnier… David [Caspe, who produces] was like, “We really packed a lot in there, didn’t we, into that 28 minutes.” I was crying/laughing. Like, why are more people not watching this show if you like Happy Endings? It’s just as good. It’s that same hard, funny sell. It’s all the same writers. Different cast, but it’s very similar in feel.

AVC: When we talked to Adam Pally a few years ago, he said that you two still talk every day. Are you still that close?

CW: We are. One of my top probably three best friends, and I love him so much. He’s my soul mate.

AVC: In your essay about the show in the book, you said that Eliza Coupe was fabulous, but she had this really funny sense of self-deprecation. But that’s also like what you’re writing about. You have this really successful career, beautiful family, but throughout the book you’re making fun of yourself. You two have that in common.

CW: We really did. Eliza is so funny and obviously, so beautiful and talented, but she can really laugh about herself. And like I said in the book, for me, it’s the greatest quality when people don’t take themselves too seriously. It’s so boring when people do that. To that point, what I said earlier about pulling “Please Like Me,” I am trying to find the balance between self-deprecation and also desperation to be liked. I did turn 40, and I think I am a confident person. But I try to live in reality, I would say [Laughs.], and with reality comes seeing your flaws and being able to laugh at the insanity of the world. You have to. Life is too difficult.

AVC: You seem like such a social person. How did you get through the past year?

CW: [Laughs.] It’s been hard for us extroverts! Obviously kidding in terms of the depth of devastation of the past year, but my friend Jessica St. Clair is an actress, and we share a very particular narrow sadness, and maybe other people do, about the loss of small talk. A lot of people don’t like small talk. In fact, my husband hates it and does anything in the world to avoid it. I seek it out. If I see anyone—I guess this is a quality from my fatheranyone a block away, I’ll cross the street to try to interact with them. People are like, “Ugh, it’s so dumb to be like, ‘How’s the weather?’” You’re in L.A.! But I crave these interactions, and I get energy from other people and like having little moments with people. So Jessica was like, “What I wouldn’t give to be able to shoot the shit more with the mail person.” We need to get to T.J. Maxx and get back to our chatting with the clerks. We need all this. This is what we’re missing most.

AVC: Are you also writing right now, for future projects?

CW: I’m not. I have an idea for a movie that I’m pitching, but I’m not really doing anything right yet. Andrew Rannells and I just wrote a movie together. And just shooting Black Monday and The Shrink Next Door. And then I’m going to take the summer off, and be with my kids. I don’t have a job [Laughs.]

AVC: What can you tell us about The Shrink Next Door? 

CW: It’s truly incredible. It’s been a dream job we’ve been working on for six months, and it’s one of those jobs you’ll never forget, both because the writing is so good, and the cast I love so much—Paul Rudd and Will Ferrell and Kathryn Hahn. But also we shot it during the height of the pandemic and the epicenter of it. And I’ll never forget it as long as I live.

AVC: Was it one of those shot like a Zoom call then because you couldn’t be in the same place?

CW: Oh, we were in the same place. We were on set, so that’s kind of what I mean. It bonded everyone, the crew and the cast.

AVC: Going back to the book, another really valuable part was when you’re writing about your weight and body acceptance in the beginning, when a manager told you that you needed to lose weight or The Hollywood Reporter saying that’s why you were fired from SNL. But obviously your job now involves a lot of physical maintenance, like in a recent episode of Bitch Sesh, you were joking about getting your face resurfaced. How do you balance those two things? 

CW: I hate it. I hate having to take time for all those things. I go back to The Beauty Myth, which I read in college. All the extra time women, I don’t want to say have to take, because it’s certainly my choice. But I feel like so much more mental and physical energy on one’s appearance, if you choose to go that route—I am an actress after all. So I’m resentful of it. Then I also love all those products, so I can’t say I hate it. But it is a good bit of struggle. That was one upside of a pandemic—there’s nowhere to be. I don’t have to sit in all these million things, outside of my kids, it doesn’t matter right now.

AVC: It seems like you come to grips with your time on Saturday Night Live in the book. Because that always seems like kind of an odd chapter, like how some really funny women like you, Janeane Garofalo, Julia Louis-Dreyfus, Jenny Slate, etc. didn’t really get a chance there.

CW: I actually look back at it with gratitude and fondness despite everything. It was a huge opportunity that I got. It definitely took a lot of processing of the disappointment. But at the same time, I was given a huge opportunity. So I don’t really think too much bad stuff about it.

AVC: What were your favorite times on it like?

CW: My favorite part was Kristen [Wiig] and Amy [Poehler], so lovely. Jason [Sudeikis], so wonderful. Kenan [Thompson] was the absolute favorite, and now my husband is working with him [on his new new sitcom Kenan], so that’s really fun. I loved being with the cast. They were so fun, to get to be around that level of of hilarious people.

AVC: You started out collaborating with June Diane Raphael on live shows and writing the Bride Wars screenplay, on to SNL, and working with Danielle on Bitch Sesh and Hotwives Of Orlando. Is there a certain way you like to work or collaborate with people or on your own? 

CW: Honestly, I think everyone’s career, sometimes people ask me, “Well, what should I do?” And I’m like, “There’s no path! There’s no one path.” And that’s actually what’s cool right now that you feel like there’s space opening up for especially women get to do different things. Or anyone just not going to have, like, one label slapped on them. I’ve always operated under a lot of like, “I’ll work on whatever seems fun or seriously, will pay me” [Laughs.]. But I love collaborating with people. And so June’s always my nearest and dearest collaborator. But it was so fun to write with Andrew Rannells, too. And obviously I collaborate with Danielle Schneider on Bitch Sesh. I also loved writing a book on my own. So I think to be creative in any capacity, I’ve been really lucky, and to do it across different media has been great.

Not to be so cheesy, but I really like living my dreams. I really don’t want for anything more out of my career. But I also think in this business, I have much less emotional reactions to things that happened that I wish hadn’t happened or that were disappointing in my career. Just from being in this business so long, I cannot give this business one more thing. But at the same time, it’s sort of been tempered because when good things happen you have to become a little numb, a little more not attached to anything. So much of it doesn’t end up coming to fruition. But I would say, especially with this book, I am really proud of it, and I’m loving this time of life I’m in.