Sarah Cooper became famous mocking President Trump, but she’ll be just fine if he loses

Celeste Sloman
Sarah Cooper in Brooklyn in October. –Celeste Sloman / The Washington Post

NEW YORK – Sarah Cooper got the message from someone named Robin late in September. By now, the news was out: Cooper, who had gone from playing a pizza place in January to chatting with Democratic vice-presidential candidate Sen. Kamala Harris by July, was getting her own Netflix special. And a series at CBS. She had already guest-hosted “Jimmy Kimmel Live!” and been declared Oscar-worthy by Cher.

But Robin was annoyed. The breakneck pace of this amazing rise had cut into Cooper’s TikTok production. In fact, it had been two months since she had posted one of her lip-synced takedowns of President Donald Trump.

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“I understand you are working on your Netflix thing, and I get that it will bring you more money,” Robin wrote on Facebook. “But is it really all that’s important? We need you to stay in his face during this critical time. Netflix will wait for you – trust me.”

Most anybody in Cooper’s position would click delete. What did she owe a stranger direct-messaging her on social media? But Cooper kept the note. And on a recent weekday, sitting on her living-room couch in Brooklyn, she was able to retrieve it for a reporter in less than a minute.

All summer, a collection of nagging Robins has filled her inbox. The requests inspire guilt, anxiety and a sense of duty to deliver.

“She takes it very literally, as if she was working at a restaurant and someone ordered soup,” says Jeff Palm, her husband.

That is the curse of being a viral phenomenon and just about the only good thing in a year mired in isolation, racial unrest and political conflict. That curse is also about being Sarah Cooper, whose biting wit is matched only by her genuine desire to not let anyone down.

A day after Robin’s cranky note, a new Cooper video debuted.

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Filmed in that same apartment, “How to Drugs” is a 64-second lip-sync masterstroke set to a recent Trump interview with Fox News host Laura Ingraham. The president speculates that Democratic nominee Joe Biden used performance enhancers to boost his debating chops. As she performs, Cooper – a 42-year-old Black woman playing a 74-year-old White president – opens a baggie containing a white substance and proceeds to messily half-snort, half-bathe herself in the powder.

Three million people had watched the clip within hours of its release.

“There’s no mimicry,” says Cher, who has been a fan since catching a Cooper clip in April. “And yet you believe this young girl with long black hair and whatever she’s wearing and no makeup and kind of sitting around her house. She’s a Lee Strasberg kind of girl,” a reference to the founder of the legendary acting school.

Harris has also been mesmerized by the performances. They led her to read Cooper’s pre-TikTok satirical management books, including “How to be Successful Without Hurting Men’s Feelings” and “100 Tricks to Appear Smart in Meetings.”

“She has figured out the significance of packaging,” Biden’s running mate says by phone. “Because packaging is an exterior. A package can look any way, but it literally has nothing to do with what’s inside the box.”

Harris pauses.

“What she does really is profound. What if it was a Black woman, Trump’s age, who parted the protesters and walked by a chain-link fence to stand in front of a boarded-up church to hold up a Bible and speak the words that were spoken? Would the response have been different than when Donald Trump did it? That’s the brilliance of what she’s done. There are so many layers.”

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In a medium where teenage gamers become instant multimillionaires, Cooper is the strangest kind of overnight star. She has earned a master’s degree, written three books and developed more than a casual understanding of John Maynard Keynes. She was in her 30s before she did her first standup set, and spent the bulk of her adult life working at tech companies, most recently Google, where she led the team that redesigned the company’s popular word-processing program, Google Docs.

Before April, Cooper’s frustration with her comedy career found her even considering a return to Google. Her books had been moderately successful, and there was another, on Zoom culture, being discussed. But she couldn’t get on the festival program of Just For Laughs, the annual comedy showcase in Montreal, never mind score a late-night television appearance.

“People were returning phone calls,” says Chris Burns, her manager. “It’s just that they didn’t have a fire lit under their a– that we have to make something with this person.”

At Google, Cooper had been making roughly $150,000 by the time she quit in 2014. Palm, whom she met at the company, had been the breadwinner ever since.

“And my mom, who is very traditional, was making me feel guilty,” Cooper says. “Like, ‘Wait, so you don’t cook. You don’t have a job. He works all day, and he comes home, and there’s no food because you don’t shop, either?’ And so I was thinking, you know what, if nothing else happens this year, I’ll go back to Google.”

Then, while listening to an April 14 news conference, Cooper heard something in the way the president talked about organizing a group to deal with the spread of the novel coronavirus.

“I’m going to call it a committee, and we’re going to make decisions,” Cooper recalls him saying. “You know, that whole thing.

“This is a guy in a meeting who has no idea what he’s saying. And I (decided I) want to be that guy. And that was it.”

She posted a very simple, 11-second clip, “How to Leadership,” on TikTok. Cooper estimates it got about 50,000 views when she first shared it.

The breakthrough came two weeks later, after Trump’s infamous news conference about the potential benefit of injecting covid-19 patients with disinfectant. This time, Cooper added multiple camera angles, props – a lamp, a spray bottle of Mrs. Meyer’s – and played a second character.

On April 23, she published the 49-second “How to Medical.”

That night, Katie Morrissey, a comedian friend, opened Twitter and saw the clip exploding. It would eventually be downloaded by 25 million people. Jerry Seinfeld retweeted it.

Comedian and former “Saturday Night Live” star Maya Rudolph also saw the video. She hadn’t heard of Cooper before. She was hooked.

“It’s weird how things hit at exactly the right time sometimes,” Rudolph says. “It’s the thing we all needed and the thing we all wanted to digest. And it just happened to take this brilliant, talented person, who does something else, to do it.”

Lacey Terrell
Sarah Cooper in “Sarah Cooper: Everything’s Fine.” —Lacey Terrell / Netflix

From TikTok to a Netflix special

On a recent morning, Cooper sat in her new glass-walled office in an otherwise empty floor of a WeWork in Brooklyn. Until recently, she shared a space here with five strangers. There’s not much to give away her presence, nevermind her enhanced stature, other than a copy of Julia Cameron’s creativity bible, “The Artist’s Way,” and her year-old cockapoo, Stella, chasing a rubber ball.

After that first TikTok video went viral last spring, Cooper had a conversation with Burns.

“Is this Trump stuff, like, a one-off?” she remembers asking him. “How does this fit in with what I’ve been doing?

“And then it was this lightbulb moment: Wait, I’ve been making fun of BS from sleazy business guys my entire life. This is what I should have been doing the entire four years.”

There is a tinge of regret in her voice, as if all of this success could have started in the days of Sean Spicer. But there is also the flip side, that she’s become popular for a very specific, viral bit when her actual ambitions stretch well beyond the less than a minute allowed on TikTok.

“You know, I have this image in my head,” says Cooper. “I’m getting onstage after this is over and starting to do my act, and then somebody in the back is yelling out, ‘We want to hear Trump!’ Part of this is you get famous for one thing, but then you’re like, oh well, there’s other things I can do.”

Rudolph and Natasha Lyonne, the “Russian Doll” star, are giving her a chance to show those other things Oct. 27, when Netflix premieres Cooper’s first special, which they produced and Lyonne directed.

It is not your standard Netflix comedy show. For one thing, “Sarah Cooper: Everything’s Fine” is not standup. The special is a darkly hilarious and political sketch show filmed on the covid-claustrophobic set of a fictitious morning program hosted by a needy and desperately cheery character named Sarah Cooper.

Cooper, Lyonne and Rudolph recruited a slate of A-listers – the full cast is being kept under wraps by Netflix, but it includes Marisa Tomei as the Devil, Jon Hamm as MyPillow’s CEO and Fred Armisen as her socially distanced producer – to capture the year that broke us.

“Obviously Sarah is such a revelation,” says Lyonne. “What she was able to transmit through those videos was something that we were all feeling so keenly – that sort of soul sickness. Jokes are really the closest thing we’ve got to a life preserver for sanity, because how else do you make sense of a riddle like the one we find ourselves in?”

Family photo
Sarah Cooper’s mother, Jennifer Cooper, holds her in Jamaica in 1978. —Family photo

Dabbling in comedy, rising at Google

It took a pandemic and some TikTok tutelage from her young nephews to spark Cooper’s breakthrough. But her take on Trump was not dumb luck. It’s easily trackable to her three years at Google as a smiling, agreeable, productive participant of boardroom America.

As she dutifully did her job, Cooper was also taking detailed notes on how the fake-it-till-you-make-its rose to the top. Targeting Trump, whom she considers the king of the bluffer-buffoons, made perfect sense.

“There is almost a social justice aspect to this,” says comedian Morrissey. “She’s been seeing people like Trump do this for years, all these guys who have bulls—-ed their ways into positions of power.”

She did not set out to stand up to a president. For years, she actually struggled to stand up for herself.

In 1995, when she was 17, Cooper wrote a contract. “I promise to never give up on my dream of becoming famous as an award-winning actress UNLESS I decide it is not really what I want or ten years of dedicated work has gotten me nowhere.”

Her older sister, Charmaine, signed as a witness.

Sarah was the baby of the family, the youngest of Lance and Jennifer Cooper’s four children, and only 3 years old when the couple decided to emigrate from Jamaica in 1980. The Coopers settled in Maryland to join Jennifer’s sister. Lance got a job as an electrical engineer at the Washington Metropolitan Area Transit Authority, a position he would hold for 17 years. They bought a home in Montgomery County, Md., regularly attended a Presbyterian church, and if they were Black in an area that was largely White, “we didn’t even see color,” says Jennifer. “And it’s funny, all of Sarah’s friends were White.”

While young, Sarah and Charmaine created short plays in the basement with Barbie dolls and later filmed mock runway shows on a Camcorder. By the time she got to high school, Cooper was acting in plays and deep into Shakespeare. But when it came time for college, Lance had a talk with his youngest daughter. He urged her not to study theater.

“She was fantastic in high school drama,” Lance says now. “That was her love. And she said, ‘Dad, I would like to pursue drama.’ And I said, ‘My dear, beloved daughter, the drama world is a hit-and-miss thing. I’m not able to provide you with subsidies all the days of your life. So try to get a profession.'”

Cooper listened to her father.

“I always assume that other people know better than me and that they know more than I do,” she admits. “And it’s taken me a long time to stop thinking this way, where I’m like, ‘No, I actually do know. I do know that I should trust my feelings.’ But definitely, back then, I thought, ‘Maybe I’m not into the theater. Maybe I don’t enjoy this.'”

Family photo
Cooper, at around 8 years old, practices the trombone. —Family photo

At the University of Maryland, Cooper studied economics, graduating magna cum laude, and went to Georgia Tech, where she would get her master’s in digital media in 2001.

“She was one of the smartest people I’ve taught, and I’ve been teaching for almost 50 years at MIT and Georgia Tech,” says Janet Murray, one of her professors.

Post-college, the pattern continued. Cooper took the occasional theater class while focusing on her regular job, whether at a design firm in Atlanta or at Yahoo in San Francisco. She didn’t even try comedy on a stage until 2010.

In a way, Cooper’s real education came at Google, which hired her in 2011 as a user experience designer.

Early in her tenure, Cooper had to assess the work of a male engineer. It wasn’t good, and so she told him so, politely but directly. In her performance review, she was scolded for not being sensitive enough.

“I learned pretty quickly that I couldn’t just be as direct as I wanted to be,” she says. “And that’s really what ‘How to be Successful Without Hurting Men’s Feelings’ is about. It’s about how women change what we say. We become more approachable and likable and make sure we won’t get that ‘threatening’ label put on us.”

It worked. Before long, Cooper was promoted, put in charge of the team redesigning Google Docs. She also became popular at work.

“There were some people who were talented, but nobody wanted to work with them,” says Antonella Pavese, who hired Cooper at Google. “I had software engineers coming to me to say, ‘Can I please work with Sarah?'”

At Google, Cooper balanced her work performance with her side projects. On the inside, she served as a kind of behavioral spy, watching men take credit for projects they merely dropped into or get praised for throwing out meaningless catchphrases. In 2014, while still working at Google, she launched The Cooper Review, a website dedicated to the sardonic lessons that would lead to her first book.

Three months later, that November, Cooper decided she needed to give her performance career one last shot.

“When I came to Google, it was like this Plan B,” she says. “It wasn’t what I came to New York for. I came to New York to act.”

The decision surprised Pavese, who took her to lunch to urge her to stay.

“Even Jeff was like, ‘I see you at work, and you’re smiling,'” says Cooper. “I even met with a life coach who told me that I shouldn’t quit yet because I didn’t have a book deal. My manager said, ‘If you need to come back, you know you can come back any time.’ So I always knew there was a possibility.”

‘The ultimate form of mockery’

Celeste Sloman
Sarah Cooper in Brooklyn in October. —Celeste Sloman / The Washington Post

It isn’t easy making these TikToks. In her WeWork office, Cooper shows the raw footage for “How to Drugs” on her iPhone. Cooper recorded 117 takes before she was ready to pop the clips into Final Cut. Trump’s speech patterns are unpredictable.

“You don’t know when he’s going to say ‘the’ versus ‘but’ versus ‘so’ versus all of these different words,” she says. “And he doesn’t either. I think he just has, like, this randomizer, and none of it makes sense.”

Cooper doesn’t wear a costume to play Trump. There’s no green screen or prop department. But her videos are anything but dashed off.

As president, Cooper’s eyes wander like a preschooler. Her Trump flips a light switch on-and-off, as if discovering a new toy. He scribbles with crayons. And the mockumentary wouldn’t be complete without another Cooper touch: She plays other characters in this pocket play. Trump’s army of yes is replaced by people who react the way real experts would if confronted by a fellow suggesting injecting a cleaning solution into the human body. Eyes roll, heads shake.

The problem with Trump, as a traditional comic foil, is obvious to anyone who watched Alec Baldwin, with wig and makeup, joylessly soldier on through another “Saturday Night Live” cold opening.

“The reality is as absurd or even more absurd than the mockery,” says attorney George Conway III, the Trump hater and husband of Kellyanne, who has not been above DM-ing Cooper for the occasional TikTok. “For Sarah, it is acting because the expressions and gestures are what makes it – as well as the fact that you have this beautiful Black woman mouthing it. It’s being disembodied from Trump, and that’s the ultimate form of mockery.”

Cooper knows what Trump has meant to her career. That doesn’t mean she’s OK with him staying in the White House to provide her with more material.

At the Democratic National Convention in August, Cooper delivered a lip-sync of Trump raging about mail-in voting before speaking directly to the audience, in her own voice, to urge people to cast their ballots. “It’s your vote. It’s your right,” she said. “Don’t let Donald Trump take that away from you.”

And Cooper is well-positioned for a post-Trump universe.

In August, CBS signed on to adapt “How to Be Successful Without Hurting Men’s Feelings” into a sitcom. Cooper will work with Cindy Chupack, a writer and executive producer on “Sex and the City” and “Modern Family.”

Lacey Terrell
Cooper in “Sarah Cooper: Everything’s Fine.” —Lacey Terrell / Netflix

Getting “Sarah Cooper: Everything’s Fine” on air before the election would have been a challenge in normal times. In this case, safety protocols meant filming many guests remotely, testing those on set daily and limiting some indoor filming to 15-minute stretches to allow for regular cleaning. There was also the uncertainty of centering an entire special on a star whose biggest previous TV gig was 90 seconds in a 2012 episode of supernatural teen drama “The Vampire Diaries.”

But Cooper showed up in Los Angeles with more than enough in her laptop.

“A crazy amount of ideas that obviously felt like they’ve been wanting to burst out of her for some time,” says Rudolph.

“I was blown away,” says Lyonne. “It was clear this was her moment, and she was just so ready for it.”

As Election Day approaches, Cooper, masked and walking Stella between her office and home, doesn’t pause when asked if she will miss doing her TrumpToks.

“No,” she says. “I think if I’m doing it for fun and not because I feel like we need to get rid of him, maybe without all that pressure, maybe it will be fun. But this has given me the career that I have. I just feel like now I get to say all this other stuff and tell all these other stories and do all these other things. That’s what I’m excited about.”

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