Catching up with Sarah Cooper

By Brian Braiker

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The year 2020 was by almost any measurement an absolute dumpster fire of a year. But for Sarah Cooper, 2020 couldn’t have gone better: The writer and comedian shot to the rarest of levels of viral fame in the early days of TikTok with her brilliant satirical lip-sync impersonations of President Donald Trump’s absurd press briefings. Her “How to Medical,” for example, has been viewed more than 25 million times and counting.

Cooper parlayed the popularity of those videos, her smarts and her telegenic looks to headline a Netflix variety special “Sarah Cooper: Everything’s Fine,” directed by Natasha Lyonne and executive produced by Maya Rudolph. This week she stars in a new coming-of-age film “Summering” and her auto-biographical take on Dale Carnegie’s “How to Win Friends and Influence People,” called “Let’s Catch Up Soon,” is out now on Audible.

Cooper is this week’s guest on “Brooklyn Magazine: The Podcast,” where she joins me for a wide-ranging conversation about her career — she left a steady gig at Google to pursue comedy — working with Jerry Seinfeld in an upcoming movie about the invention of the Pop-Tart, living in Brooklyn, divorce, Trump and winning friends and influencing people.

Here is an excerpt of our interview, lightly edited for readability and flow.

“Summering” is out now. Is it fair to characterize this as “Stand by Me” for girls in 2022? Or is that just kind of a facile shorthand?
I mean it’s pretty reductive and offensive, but no. It is pretty much that. It’s a coming of age story about four young girls who have their last adventure before middle school. And so it’s really about that innocent time before you go through puberty and everything falls apart and they have this adventure where they find a dead body and they decide to discover or try to figure out who this man was, what kind of life he had.

And it’s your first feature film, right? Something that probably would’ve seemed inconceivable four years ago.
I mean not according to my mom. My mom always saw it happening, but for me yeah, my agent, everybody was like, “Yeah, it’s not going to happen.” I mean 2020 was a dumpster fire of a year for a lot of us.

Not for you.
For me it was the best year in my life.

This movie in particular, what do you want people to take away from it? What was important to you about it?
“Takeaway” is such a corporate thing. What are the takeaways here? James Ponsoldt — who’s the director and he also co-wrote it — he kind of imagined these four girls coming from four very different backgrounds and this idea that we shouldn’t really judge people based on just what you see because the context of their life basically determines who they are. But it’s also just kind of a fun journey into the minds of these little girls.

Let’s go back to how you got here, your early career. You’ve done time at Yahoo, at Google.
Done time, yeah. I was a designer for Google Docs.

Oh, can I complain to you about the new Gmail roll out?
Please do. Every time I look at it, I complain in my head and I’m like, “I know exactly what’s going on. I know what’s happening with the product managers and the engineers and they’re arguing about this. And now this is how it showed up in my face. And I’m so angry about it.”

So Google Docs. Design? UX? What was the gig?
Exactly, UX. A lot of people don’t know that term, but yeah, it was user experience design. If you see a button that you like, I did that. I designed user flows, the default font that you see, I picked the default font. I’m really into fonts. I love fonts. That’s how I meditate: Sometimes I’ll get high and I’ll just look at fonts.

You’re there, you’re in tech and obviously that was not destined to be where you were going to live out your days.
When I was little, I wanted to be a singer. I couldn’t quite get the singing thing down. I just loved performing, but I come from an immigrant family and they were like, “No, you’re never going to be able to afford a house with an acting salary, so you need to do something that’s smarter than that.” So I did economics. I don’t know anything about economics, so I’m not sure why that was more useful than a theater degree. I wanted to play parts on stage, but my parents wanted me to become a different person altogether, they wanted me to become someone who cared about economics. I couldn’t do it.

That’s a classic immigrant story, right? Or first generation American story. Your family’s Jamaican, is that right?
I was born there.

When did you come over here?
When I was 3, I came here and I immediately assimilated. I was correcting my parents, they were speaking in Jamaican patois and I was like, “Mom, Dad, that’s not actually how that’s pronounced.”

Parents love that.
They just love it. They created a little Republican. I just assimilated very quickly, and I think that’s why I wrote about “How to Appear Smart in Meetings” is because I was in these meetings and I was like, “I’m just observing all of these men talking about whatever they’re talking about.” But they don’t actually, if you really listen, they’re not actually saying anything. And so I was like, “How can I pick up that language?”

This is when you were at Google, right? You wrote the book “100 Tricks to Appear Smart in Meetings.”
Exactly. Yeah, that was the first thing that went viral was an article called “10 Tricks to Appear Smart in Meetings;” that was on Medium. And I had been writing that since I worked at Yahoo actually, I was in a meeting and somebody was like, “Yeah, 25 percent of people clicked on this button.” And somebody [else] was like, “Oh, about one in four.” And I was like, “Wow, that was brilliant.” They didn’t add anything to the conversation, they just said it in a different way, and now everybody thinks they know math and I wrote that down. So I came up with the other things, like ask if it’s going to scale and ask for the data or whatever it is, and it went crazy viral.

Did that give you the courage to leave Google? Or were you like, this is fun to go viral, but how do you make money at it?
I think because I had a source of income in my ex-husband, it was easier for me to leave my job, but that went viral, millions of people were reading it and I was like, “Oh, I have an audience. If I create content that resonates with people, you can find an audience.” And so it gave me the courage to leave, but it was hard leaving Google because you work at Google and you’re not happy, you’re just like, “If I can’t be happy here, I’m not going to be happy anywhere.”

So what’s the trajectory then? 2020 comes, you’re hosting comedy club shows, I guess comedy nights. I read or I heard an interview where you said that you were almost not sure you were going to do comedy anymore before the Trump lip syncing videos happened.
So I left Google in 2014 and then by 2019, I’d written “How to Be Successful Without Hurting Men’s Feelings.” But by the end of 2019, I was like, “I need to go back to Google, I need a 401(k). I’m getting older and I don’t know how I’m going to support myself.” And I decided my ex-husband was mad at me because I wasn’t making money. Turns out he was just mad about everything all the time, so it wasn’t me. And so by 2019 I was like, “Yeah, I’m probably going to just try to go back to Google.” And then the pandemic happened and then I made the videos and then, that was it.

What worked so well with those videos was just separating the visuals of his face and just hearing his voice and your sort of interpretation of it, which really highlighted the absurdity of what he was saying. How by design was that?
It all comes full circle back to “100 Tricks to Appear Smart in Meetings” because I looked at him in these Covid press briefings. And he was saying absolutely nothing much the way these tech guys were saying absolutely nothing, and yet he had the presidential seal, he had people calling him sir, everyone’s nodding behind him. And if you listen to what he’s saying, he’s not saying anything. I remember specifically the quote where it hit me, they were like, “Well, how are we going to do this?” And he goes, “Well, we’re going to form a committee, and it’s going to be a good committee, and we’re going to make decisions, and we’re going to make decisions fairly quickly, and I think they’re going to be the right decisions.” And I was like, “You just said nothing; you said absolutely nothing.” And so that was the first little clip that I lip synced, and it was literally out of jealousy because I would love to be a person that just said nothing, and people thought I was the most brilliant person in the room. I would love that.

I bet you wouldn’t.
No, I would. But also his confidence in feeling like he’s the smartest when he’s not, when he’s literally the dumbest.

Delusional people are funny.
Delusional people are funny, but I also would love to be that deluded. I mean I don’t want to be a narcissist, but at the same time their lack of awareness about how people see them or how they’re perceived is actually I think kind of a superpower, you know what I mean? Because you just don’t care what people think, you know you’re the greatest, you’re smarter than all the doctors and all the military people and you’re smarter than everybody. And it’s, wow, to have that level of confidence and yet nothing to back it up, that’s amazing.

Do you miss him at all?
I don’t miss him, although just the other night, there’s a quote where he’s talking about how if you plead the Fifth Amendment, you must be part of the mob. And I was like, “That would be a pretty good one to do right now.”

At what point did you realize, well, “I can’t do this forever? I don’t want to be a one hit wonder; what’s my next move?”
The moment I thought that is when my new agent told me that. They were like, “Yeah, this can’t be the only thing that you can do, and also your name is forever tied to the name of someone who might be the worst person who ever existed, and so that’s tough.” So by the end of 2020 I made the decision I’m not going to do those lip syncing videos anymore, even though literally every day, even yesterday, people are like, “Make another one, please.” It’s really hard.

But then you do “Everything’s Fine” on Netflix and all of a sudden you’re going from TikTok videos that you’re making yourself, and you’re working with Natasha Lyonne, you’re working with Maya Rudolph and Fred Armisen. Was that scary? Was it intimidating or was it just a fun ride?
I had no concept of it because I feel like I wasn’t stressed. I wasn’t stressed when I met Helen Mirren, we were on Zoom rehearsing this bus scene and she was trying to lip sync and I’m teaching literally the greatest actress ever how to lip sync. Why am I teaching you how to lip sync? This world doesn’t make any sense. And she wasn’t getting it, I got to say it. Helen, you weren’t nailing it.

You’ve also got “Let’s Catch Up Soon” out now through Audible. It’s your sort of autobiographical riff on Dale Carnegie’s “How to Win Friends and Influence People.” What was your assignment? And did it change at all while you were sort of riffing on the book?
Oh yeah, it changed a lot. Audible approached me about doing a modern take on Dale Carnegie from a woman’s perspective. I mean I’d heard of the book, but I hadn’t read it, but when I read it, I was like, “This is stupid.” All of these principles for how to deal with people, like smile, remember people’s names, give compliments, make people feel important. And I was just like, “I’ve written this book, it’s called “100 Tricks to Appear Smart in Meetings.” These are tricks. I dug a little deeper and realized he was saying you have to do these things, but you have to do them authentically. You can’t just smile, you can’t just give a compliment, you have to actually like the thing that you’re complimenting, otherwise you’re not making a real connection with the person. The first piece is smiling. As women we’re told to smile so much that it feels like we’re …

Like, “Fuck you, I’m not going to smile.”
Yeah. Exactly. But then realizing it’s really not about smiling, it’s about being excited to meet people and I wasn’t excited to meet people, but I knew that if you don’t look like you want to meet people, no one’s going to want to meet you. So you actually do have to figure out how you can get that excitement when you meet someone. And so the second chapter is really me accepting the lesson and trying it out in the real world. You realize, oh, if you want to have longer-standing relationships with people, that’s the first thing you need, is to remember their name. It’s just a basic, basic thing, and it’s given me the opportunity to make friends with people that I never would’ve made friends with before, just by asking for their name and remembering their name.

So the actual Dale Carnegie book, “How to Win Friends and Influence People” was helpful to you in the end?
It literally changed my life, and there was one big principle which is [to] be genuinely interested, which I was like, “How do you be genuinely interested?” I’ve spent my whole life pretending to be interested in things, and I didn’t know what genuine interest was, and it starts with knowing what you’re interested in. I had to say, “Okay, this is what I love. This is comedy, I love comedy, I love writing, I love getting high, I want to meet other people who want to do those things.” And once you realize who you are, you can find other people who have similar interests and then you can make genuine friendships and you don’t have to fake being interested anymore because you are actually interested.

You talked about divorce earlier. Is it hard to date at this point in your life? Are you working so much or you’re just free and you can do whatever you want? You must have access to the celebrity level of dating if you are so inclined.
Oh yeah, I’m just dating. Jon Hamm, Jamie Foxx, who else am I dating? Just dating everybody. The Hemsworths.

All the Chrises.
All the Chrises. Yeah, I’m just dating everybody. I don’t know, I think I just have really high standards, so it’s really hard for me to meet people. It’s weird because I was in my 30s I was dating to meet “the one” and now I’m like, “I don’t want to meet the one.” I just want to have a good time. It’s really just about meeting someone who is excited about their life, that’s literally all it is. If you’re excited about your life and you can have a good conversation, that’s the bar at this point. I’m not looking for a relationship, I never want to get married again, I’m done with that scene. I never want to combine financials with someone again.

Talk about “Unfrosted.” You’re doing a movie with Jerry Seinfeld about the true story of the Pop-Tart. Just Jerry Seinfeld, Pop-Tart, without knowing anything else about it, I’m already laughing. The cast is ridiculous, Melissa McCarthy, Jim Gaffigan, Amy Schumer, Hugh Grant.
I don’t know how much I’m allowed to say about it, but I just wrapped. I was filming for a few months in LA. And it takes place in the sixties, it’s literally “Mad Men” meets “Seinfeld.” It’s like the look of “Mad Men” with just the most ridiculous, silly plots you’ve ever seen in your life. It’s basically a parody of the space race between Kellogg’s and Post to see who can come up with the Pop-Tart first. It’s just a ridiculous, ridiculous story, but you’re just laughing the whole time.

Did you pick up anything from Seinfeld?
I was really impressed with him because he’s … [Laughs] “I’m really impressed with Seinfeld.”

Yeah. I think he’s going to make it.
I think he has a future. What did he teach me? Well, he taught me about embarrassment. We all want to avoid feeling embarrassed, but when you’re performing, you feel embarrassed a lot. Jim Gaffigan tells this story, which is basically the entire industry is like, “Come here, come here, come here, come here.” And then as soon as you get close, they slap you across the face. And that’s how it feels. You want to be there, but at the same time it can be just very humiliating. And so he was like, “You just feel embarrassed, then you move on and then you move on and you keep moving on.” And so he’s very resilient that way. And so it was really just amazing to watch. Watching him do all of those things was incredible.

“Don’t be embarrassed.” So it all comes back to Trump really in the end. We should all strive to be more like him.
Yeah we should. We should. We actually should. I think the people who are good, genuine, kind people do need to be more assertive, shameless. Because we are the ones who actually want to help, so we should be. It kind of sucks that the people with the loudest voice are the ones with the worst ideas usually.

Do you have a perfect Brooklyn day?
My perfect Brooklyn day is it’s raining. I go to my coffee shop, I get an oat milk latte and a croissant, I have the corner booth, I have my laptop, I get high and I write all day, that’s my perfect day.

You can write high?
I love writing high. It’s my favorite thing in the whole world. It’s not good when I’m writing, but I’m enjoying it.

Write high, edit sober. Is that the thing?
Write high, edit sober, submit drunk.

Check out this episode of “Brooklyn Magazine: The Podcast” for more. Subscribe and listen wherever you get your podcasts.