The Washington PostDemocracy Dies in Darkness

Amanda Seales was always ‘Smart Funny and Black.’ Finally, everyone else sees it.

Actress Amanda Seales, who plays Tiffany DuBois on HBO's "Insecure", talks about the show's success in representing the full spectrum of black women. (Video: Ashleigh Joplin/The Washington Post)

What happens to a moment deferred?

Does it slip through the cracks of YouTube, never to be replayed?

Retire to the island of old tweets to shrivel in the sun?

Or does it quietly gather a viral army of followers too big to ignore?

The secret may lie with Amanda Seales, a comedian (and actress, and singer, and poet and painter) who after nearly a decade is finally undeniably having a moment.

Perhaps you caught her schooling Caitlyn Jenner during Katy Perry’s “Dinner and Discourse” last year? How about her scene-stealing one-liners on HBO’s “Insecure”? Or her appearance on “Def Poetry Jam”? The stint as an MTV VJ? The guest appearance on Q-Tip’s last album? Opening for the Roots? Delivering that unapologetically black stand-up set on “Late Night With Seth Meyers”?

“I’ve had a couple of breakouts,” said Seales, 37, during a recent interview at the Watergate Hotel.

Smart Funny and Black,” the live black-pop-culture game show Seales dreamed up in her living room, has landed in the plush and rarefied halls of the Kennedy Center. The show is a live Quidditch match of wits mashed up with SNL’s “Black Jeopardy” sketches and a three-piece band.

Confused? Basically it’s quintessential Amanda, whom for years the entertainment industry’s gatekeepers just didn’t “get.” She bursts onto the stage wielding a microphone and gold lamé leggings, the evening’s “headmistress.” During the show, two famous funny folks (Tiffany Haddish, Estelle, Bomani Jones and Angela Rye have been guests) compete in games written by Seales for the title of “Master Blackspert” by debating categories handpicked by Seales such as “baby hair” and “in da streets Barack Obama.” The show’s tag­line: “By any joke necessary.”

It’s a celebration of blackness, and it’s been sold out for weeks. That’s because of Seales, who has more than a half million followers on social media, where she loves being her “authentic self” and her frequent posts — calling out racists, bad boyfriends and her domestic shorthair ­Lando Catrissian — have bolstered her career as a truth-teller who tells jokes.

The popular comedy tour is a big friggin’ deal, okay? This is also a familiar runway for Seales — being wheels up, poised for takeoff.

“When you’re so multitalented,” explained Seales’s friend Bevy Smith, the SiriusXM host and fairy godmother to many, “it’s very hard for the entertainment industry to get it because they like you to have one note until they tell you you should try something different.”

Seales was first poised to break out in 2004. Then a 23-year-old hip-hop head from Orlando, she’d been hired to host “Sucka Free Sunday” on MTV2. It was her first brush with fame and paying rent when the rent’s due. The buzz was palpable.

Broadway star Brandon Victor Dixon, Seales’s “brother from another,” tried to prepare her for what was coming. “Are you ready?” she remembered him asking in an intense stage whisper.

“It was so dramatic,” recalled Seales between laughs. “And I was like, ‘For what?’ And he was like: ‘For. Your. Time.’ ” She cackled. “And within a year I was laid off — but it was a moment!”

It took Seales 10 years to get back to that level of fame. “Ten long subway train years,” she said. In between she made her own music, painted political art, produced funny Web series about pop culture and gave college lectures about street ­harassment. (Seriously, that MTV money paid for the last semester of her master’s in African American studies at Columbia University).

“I’m an artist through and through,” she said. “My thing about creating things is that it has to do two purposes: It has to serve me creatively but also has to serve the people.”

In 2011, another moment came. Hip-hop didn’t feel like home anymore. So she decided to dive into comedy for real. She changed her stage name from Amanda Diva (“it just felt stupid”) to her government name, Amanda Seales.

“I have a theory that when you’re lost on the path, go back to the beginning and try the maze again,” she said.

If there's one thing Seales does not do, her friends say, it is wait for permission. At least not anymore. One network executive told her that she was "just another dumb talent" and that she seemed more like a "sidekick" than a lead. After being told by countless others that they simply didn't know what to do with her, Seales had yet another aha moment.

“I don’t need to change. I just need to diversify my realness,” she explained at a question-and-answer session two nights before her big show in Washington. The crowd, gathered at the Wing, reacted with snaps and umm-hmms.

The Georgetown pit stop was a testament to just how diverse Seales’s particular (and quantifiable) brand of realness is.

On social media, she’s about authenticity. Really. That’s not a studio line or a gimmick. “I really just be in my house,” she explained to the crowd at the Wing, referencing her prolific “PSAs” in the form of no-makeup Instagram videos about “empowering your ego” and self-care. “And I’m single, so there’s time.”

Spend even a short amount of time with Seales and you can see why folks either love her or — well, she doesn’t really care about the other side of that proposition. The unfollow button is there for a reason. Her Instagram bio: “I’m not 4 everyone.”

“I really mean that,” Seales told me later.

She might not be “everybody’s favorite box of cereal,” said comedian Roy Wood Jr., another friend, but that’s the point. Seales has “built a career on swimming the other way,” he added.

“Amanda’s that relative who could come to Thanksgiving dinner and say, ‘Hey, y’all, I got something to say,’ and everybody’s like, ‘Uh-oh.’”

So how exactly do you define someone who is a "a multi-hyphenate self-generator," as Seales's agent, Mark Gordon, calls her.

Seales is a one-woman show in the most literal sense; sitting across a couch from her, the space somehow feels crowded. Her face can cycle through a dozen expressions in as many seconds. She does voices (her Caribbean mom, the white girl, the publisher — yes, she’s coming out with a book). But she doesn’t code-switch. That’s not part of who she is.

“Amanda doesn’t like to be filtered,” said Valeisha Butterfield Jones, the global head of women and black community engagement at Google, who has known Seales since the two were coming up in New York’s hip-hop scene.

Less than 10 minutes into Seales’s “Smart Funny and Black” show at the Kennedy ­Center, the comedian had already put the white people in the theater on notice. “Know your place,” she tells them. The show, a celebration of black culture and black people, doesn’t exist to “soothe your guilt,” Seales added.

Then she took the crowd on a nearly two-hour road trip through African American popular culture and history. There were singalongs, shout-outs and sidesplitting laughter. Seales is headmaster, preacher, choir director, storyteller, ringleader. In her house, everyone knows the words to the “A Different Worldtheme song and everyone can hit that high note at the end.

By the time the third season of “Insecure” airs (the premiere is Sunday night on HBO), Seales will be nearly 20 shows into her “Smart Funny and Black: Lituation 101” tour. Of the 23 shows, 21 were sold out.

Is that success to her?

“Exactly what I’m doing is what success looks like,” she said. “I get to create on my own terms, on my own timeline, and I’m able to support myself and my mom and my cat comfortably.”