Keith Powell’s Time to Shine

The Delawarean is building his Hollywood legacy as an actor, writer, and director

In recent years, Keith Powell has been using his platform to tell his stories or stories that he knows.
Photo by Stephanie Girard.

Timing often seems to make things work in actor/writer/director Keith Powell’s favor.

Out & About Magazine last highlighted the St. Mark’s High School and Wilmington Drama League alum in October 2015. When he posted pictures on social media in April that documented his experience directing a Season Three episode of Apple TV+’s Dickinson, it seemed appropriate to feature him once again and discuss the likely 2022 return of Dickinson. So a July interview was scheduled.

Little did anyone know that Powell would decide to release his latest short film, In White Places, to the general public — online — the weekend before the interview (The film actually debuted at the Santa Barbara and San Luis Obispo film festivals in March).

Powell says he didn’t know if he was going to release the film to the public, much less when. “I sometimes just make things and don’t know if they’ll ever see the light of day,” he says. “July Fourth was coming up, and instead of writing a long post about the sins of America, I said, ‘Why don’t I just show this?’”

In White Places opens on a Black man wearing a courier’s uniform, with Powell opening the door to sign for a package around 30 seconds in, but not before a White woman skitters away at the mere sight of the courier at the curb. It’s not the last awkward interaction the characters have with the White neighbors before the 10-minute film ends.

The topic of racial stereotyping is timely, but the origins of the film aren’t new. “I always wanted to create a TV show around my best friend Lew as a mailman,” says Powell. “I wrote a piece about delivering a package to a house and [the delivery] is going weirdly and wrong. I took that little piece out and expounded upon it to create In White Places.”

Lew is Lew Indellini, front man for Wilmington funk/rock band Special Delivery and former postal carrier, who met Powell in 1996 when he was cast in a Wilmington Drama League play that Powell wrote as a teen.

Indellini says he isn’t surprised that this film has come to life. “I feel like now that he’s firmly on his path as a triple threat artist and storyteller, it hasn’t been so much the timing but more of the ‘about damn time’ that he’s getting to put more of his work in front of more and more eyes and ears.”

The Creator

A short film, Powell says, should have a lasting impact and spark a conversation. With In White Places, he wanted to create a short story to “ask the audience whose house they were fighting over in this neighborhood.”

“In my mind, the house is America,” he says.

Powell’s career has included plenty of roles that could easily be written off as lighthearted, but the Black experience is common to all of them, whether he’s performing a role or inventing one.

Of his career origins, he says, “I wrote a play when I was at St. Ann’s in middle school that was part of a school assignment. I didn’t want to be in it, I just wanted to direct it. I didn’t know what directing was, but I knew that I wanted to force people to do what I asked them to do.”

“I want to create a legacy and I want to do it through film,” says Powell.

By high school, he knew he wanted to be an actor and a director, and his private school education only emphasized that he “was the Black kid in White spaces. And being the ‘other,’ you would either embrace being the center of attention or run away. I embraced it and I wanted to tell stories that were about people like me. I didn’t feel like I was being heard because I was the minority.”

Kathy Buterbaugh was production manager for the Wilmington Drama League, where Powell wrote, directed, and performed in several one-act plays as part of the Chrysalis Players. “His plays were always far from conventional,” she says, “filled with passion, wit and plenty to raise questions in an audience’s collective mind.”

Powell found his first measure of fame as an actor, playing Toofer Spurlock, the Harvard-educated writer whose failure to manifest a single Black stereotype was an ongoing punchline on 30 Rock, which ran from 2006 to 2013.

Since then, he’s had big roles on small shows, such as About a Boy, and small roles on big shows, like The Newsroom (with Delaware’s John Gallagher Jr.), Grace and Frankie, Lucifer, and a recurring (and, reportedly, continuing) role on This Is Us.

On the big screen, he played a Tuskegee Airman in Night at the Museum: Battle of the Smithsonian in 2009. Last year saw the release of Marvelous and the Black Hole at the Sundance Film Festival, with The Beta Test slated to follow this year.

But more and more in recent years, Powell is telling his story, or stories that he knows.

In 2015, he released a series of 12 shorts called Keith Broke His Leg. As the series was being shopped around to networks, it picked up a number of independent film awards along the way.

While some of the episodes tackle topics any human might experience, such as interruptions to leisure activities, the Black experience makes many cameos.

In the episode “Baller,” Powell’s agent convinces him to do a voiceover for a commercial using an extreme stereotype of a Black voice.

Powell says that the voice he used, “is an exaggeration of what I’ve had to do, but I have had to change voices. And it got to the point [in auditions] where I just started acting like that from the moment I walked into the reading room so that they didn’t have a preconceived notion in mind.”

“So much of the work that I do is convincing people outside of their stereotype and outside of what they project Black people to be,” he says. “So much of my work is about being who I am and not who someone wants me to be. I’m never what they have in mind. So much of my work is about having to overcome or subvert or plow through that.”

In the Nick of Time

Powell may have a secret weapon when it comes to telling his story: his wife, visual artist and actress Jill Knox Powell. She co-starred with him in Keith Broke His Leg, and years later that show’s producer made an introduction that led to the pair being cast as a married couple in Connecting.

The duo’s origins show that timing, once again, has been everything.

Back in 2006, Powell was planning to fly to Los Angeles and crash on a friend’s couch when a New York agent suggested he audition for 30 Rock. He got the role, and remained in The Big Apple.

Forward to 2009, when Keith turned up late for workshopping a play, causing newly-met castmate Jill Knox to call him a loser. A few weeks later, the two had a chance to turn things around during some idle time between rehearsals.

“We talked the entire three-hour break. Been together ever since,” he says.

Time for Growth

By the time this article is published, the Powells are due to become third-time parents. Family is also an important theme of Powell’s work.

The episode “Lullaby” from Keith Broke His Leg documents the start of his nuclear family’s journey. Says he: “I wanted to write about that first moment that you want to be a parent.”

Powell continues to tell his family’s story, including loss and subsequent joys, which include the 2018 stillbirth of son Greyson, followed by the 2019 birth of daughter Dolyn.

Keith Powell says the Black experience is a common theme in much of his work, whether it’s a role he’s playing or a project he’s created, like In White Places.

“[There’s] a theme throughout all my work,” he says. “It’s about legacy and what we pass on to children and what we’ve inherited as children. This theme runs through all my work even before Greyson died, [and that’s] because Black people have been denied lineage.”

Train Baby, a 2015 film Powell co-wrote and starred in, is, according to Powell, “a movie about a man who wants to deny his heritage, and who wants to create a new line for himself.”

He adds, “Sophie’s Quinceañera is probably the most successful artistic endeavor that I’ve had. It was written on the night of my son’s funeral. It is about having that succession, what you pass down onto your children and what they take away from you.”

By successful, Powell means that Sophie’s Quinceañera played at larger film festivals than his other work, and artistically it was a wholly fulfilling work, getting him “out of a dark hole of depression.”

Even In White Places, Powell says, is about trying to build something for the next generation.

“That’s just a prevailing theme for my work. I didn’t even realize how much it occupied my brain, but legacy is important to me.”

At the time of the interview, Powell was in Atlanta to direct an episode of a new Freeform show Single Drunk Female. He directed an episode of NBC comedy Superstore in 2018, and 2020 brought Dickinson, an anachronistic and comedic period take on the life of Emily, to his directing resume.

About Dickinson, Powell says, “[It] was one of, if not the most, artistically fulfilling experiences of my life.”

Meanwhile, his fantasy job opportunity could be just on the horizon.

“I want to create my magnum opus, and I believe that will happen in television,” he says. “I want my Mad Men. I would love to direct a feature film that has a tremendous cultural impact. I want to create a legacy and I want to do it through film. If that means the medium is television . . . as long as it’s on film.”

Neil Casey is another one of Powell’s many former Chrysalis Players colleagues who has achieved success in the entertainment industry. He was a Saturday Night Live writer, played the villain in Ghostbusters, and is currently a writer on Amy Poehler and Nick Offerman’s NBC series, Making It.

Of Powell’s trajectory, Casey says, “His passion and excitement for everything that he does is really infectious and he brings his best to everything he does. He brings out the best in everyone else, too, which is part of why it’s so natural he’s becoming in demand as a director.”