Dave Chappelle at Radio City Music Hall in New York earlier this year. (Mathieu Bitton)

Comedian Dave Chappelle's mention of the D.C. Public Schools during the 2017 Emmy Awards in September was the sort of absurd eruption that live television and the Internet love. As he and Melissa McCarthy strayed off script before presenting an award — after Chappelle himself had already scored an Emmy a week prior for his post-election appearance on "Saturday Night Live" — Chappelle told the audience, "Now I'm going to read this teleprompter. Please forgive me. Shout-out to D.C. Public Schools." John Oliver soon picked up on the random reference ("Like Dave Chappelle, I would like to unexpectedly thank D.C. Public Schools because I think it would be great if it started trending on Twitter for no reason tonight whatsoever") — and the next thing America knew, #DCPublicSchools was indeed trending across social media. The school system deftly responded with its own tweet of a little girl looking cutely astonished.

The aside may have seemed casual, but Chappelle, 44, is in fact deeply devoted to the D.C. public school that he graduated from in 1991: the Duke Ellington School of the Arts. Less than two weeks after the Emmys, when he was in town for a series of stand-up shows at the Warner Theatre, Chappelle took the opportunity to visit Ellington. I thought it was a good chance to explore how a D.C. school may have helped shape one of the great comic artists of our time.

Chappelle has been returning to Ellington since early in his career. From his first breaks in television and film through the creation of the groundbreaking “Chappelle’s Show” in the early 2000s and his periodic comedy specials since, he has stayed in touch with teachers and classmates. He’s a financial supporter of the school, which must raise $500,000 a year for its specialized arts curriculum. Two years ago, he gave the commencement address.

This time, students filled the state-of-the-art theater of the newly remodeled building, waiting for Chappelle. They started scream-cheering as he pulled up a stool onstage. “I’m not going to lie to you: I hated school,” he said. The students hooted appreciatively at this off-message crack in the presence of star-struck school and city officials, who had just handed Chappelle the key to the city.

However, he continued, after he graduated and almost immediately enjoyed success, he began to appreciate what Ellington did for him. And as a token of thanks, he said he had brought a gift. The students’ screams exploded again when they saw the golden trophy: Chappelle’s Emmy. “I want you guys to have this, just so you know that even though the odds are wildly against it, this can happen for you,” he said. “And every once in a while, you guys take a look at it, and just know that I started earning this Emmy at this school.”

Chappelle presents his alma mater, Washington’s Duke Ellington School of the Arts, with the Emmy he won this year. (Jahi Chikwendiu/The Washington Post)

Chappelle's path to Ellington was indirect. He grew up in Silver Spring, Md.; Yellow Springs, Ohio; and Capitol Hill, spending time in his parents' separate homes after their marriage ended when he was young. His late father, William David Chappelle III, was a music professor and social activist, and his mother, Yvonne Seon, was a pioneer in establishing African American studies as a university discipline. When he moved back to Washington to attend high school, he started at Eastern, but he was having trouble adjusting. And he wanted to get out.

His mother bought him a Time magazine with Bill Cosby on the cover, which inspired him, at 14, to plot a career as a comedian. “For him it was a calling,” Seon told me. “I knew that was the direction he wanted to go in, and I was going to support him to find his way.” She urged him to visit comedy clubs, where an older comedian told him that to become a comedian he should study acting. After less than a year at Eastern, he and his mother decided he should transfer to Ellington. He almost blew his audition for the theater department, though, when he forgot parts of his monologue. As he recalled during his recent visit to the school, one of the audition judges asked why he wanted to act. “I don’t want to act,” he replied. “I want to be a comedian.”

When young Chappelle crossed the portico of the historic school for the first time, he found himself in a new world. “This was the pinnacle of my formal education,” Chappelle told me after his address to the students. He never attended college. “I was really oddly prepared for what I faced once I got out of high school. A lot of it just had to do with them cultivating confidence in taking risks in artistic expression, which is not an easy thing to do, and in the context of today is becoming increasingly more difficult. To express yourself freely without fear of repercussions.”

Chappelle mentioned classes that had an impact, including non-arts courses in subjects such as D.C. history and street law, and a workshop on how to engage with police officers. He took classical acting, modern acting, improvisation, technical theater and script analysis. But rather than detailing specific life-changing epiphanies, he circled back to a broader spirit of support that he felt in the Ellington environment.

“Just becoming more broadly culturally aware,” he said. “It kind of unpacked me out of whatever box that I was in and put me in proximity with different walks of life. ... There was an idea that people were very invested and interested in our well-being that was ingrained in the culture of the school. And I think the students were actually invested in one another’s well-being.”

One factor in his Ellington preparation seems mundane, yet he referred to it both in his speech and during a tour of the building, as if it might be key: the long hours. Students take traditional high school courses until early afternoon, then pursue one of eight arts majors until about 5 p.m. Rehearsals, exhibitions and productions typically keep them at school into the night. "Years later," he said in his address to the students, "when I had my own television show and I was working 16-hour days, it felt easy to me because I had school days longer than that."

Former teachers and classmates are left to sift for their own clues as to how Ellington helped mold Chappelle. The image of the tall and skinny teen donning tights to play a prancing horse in a daring production of "Macbeth" set in Haiti remains vivid. "He did not delude himself to believe he was going to be the next Macbeth," says Tia Powell Harris, who taught in the theater department at the time and now is chief executive of Ellington. "After all, he was the horse. But he knew that the training and preparation that came out of that experience were going to serve the thing that he did want to do. And he was very clear about what he did want to do. He was very good about taking what he needed and leaving the rest behind."

After full days at Ellington, Chappelle spent many nights at clubs such as the Comedy Cafe and Garvin’s. These were like internships that the self-starter arranged for himself. His mother chaperoned. He joked about Jesse Jackson running for president and ALF’s spaceship landing in a black neighborhood.

Harris caught his act one night. “It was these kernels of ideas made big,” she recalls. “I thought I was going to be rolling over laughing ... and I wasn’t, because half the time I was thinking.” She saw a certain professionalism, a command of the stage and a rapport with the audience that she considered an Ellington stamp.

By day, Chappelle’s teachers could sense an idiosyncratic mind at work. “He was interested in the thing that makes something happen, the motivation behind things,” says Donal Leace, whose theater history class was a freewheeling forum for students to try out monologues and scenes. Years later, in tribute to one of his favorite teachers, Chappelle brought a camera crew back to Leace’s classroom to film a scene for “Chappelle’s Show.”

One of Chappelle’s chores as an underclassman was to sweep the stage. “I noticed him because he was paying attention,” says Tracie Jenkins, a senior at the time. “Usually when you’re the freshman in there, you’re sweeping the stage to get it over with and goodbye. But he was checking in and listening and observing. So you felt him when you were in rehearsal.”

Chappelle has the same memory, from his point of view: “I used to watch the seniors dance and all that stuff. It inspired me. And made me want to do better. And we all pushed each other in a real friendly and loving way.”

Jenkins, who is now director of arts at Ellington, saw Chappelle when he hit New York, where, just months after graduation, he made it into some of the hottest comedy clubs. "He owned the stage and everybody in the room," Jenkins recalls. "From sweeping the stage to owning the stage."

“We don’t make the stars here,” Harris says. “They come with something, and we give them the technique and creative freedom and the humanity to do that thing. ... Dave came with something, and we gave him what we could. I would tend to believe that he would have kept going in that direction even if he hadn’t come to Ellington. But we readied him for an immediate jump into that place.”

On his tour through the school, Chappelle views a painting by student Jada Michelle Logan Smith, center. (Jahi Chikwendiu/The Washington Post)

A few hours after seeing Chappelle speak at Ellington, I watched him perform at the Warner. In the tradition of Lenny Bruce and Richard Pryor, he is fundamentally a storyteller. "We learned a particular way of doing it at Ellington," Jenkins would tell me. "There are all of these pieces and parts that you have to have in building a story that I have definitely seen in his work."

He started the show by saying that, for inspiration, he writes punchlines on scraps of paper and keeps them in a jar. When he needs new material, he’ll pull out a punchline and write a joke to go with it. To illustrate, he gave an example so unprintable and disturbing that it was inconceivable to imagine what the setup could possibly be.

Nearly an hour later, the performance reached its emotional peak when Chappelle asked for those not born in the United States to raise their hands. He was about to give a history lesson, probing the motivation behind the things that happen — just as Leace remembered him doing in high school. Addressing himself to a Pakistani woman, he proceeded to tell the story of Emmett Till, whose murder and legacy he got around to relating in a mind-bending Chappellian way to the election of Donald Trump. He ended not just the lesson but the entire show with the same profane punchline that he had planted in the beginning — and it worked, in its own shocking way. Only then did it become clear that the entire evening was one long story about making comedy, inlaid with smaller stories about Chappelle’s America.

Earlier that day, after his speech, Chappelle had strolled through Ellington’s light-filled atrium. Groups of students representing the school’s artistic disciplines were stationed around the room to give quick demonstrations of their work. As he proceeded from station to station, Chappelle was treated to literary media students riffing on James Baldwin; theater majors updating Edgar Allan Poe; dancers fluttering in the spirit of Alvin Ailey; musicians jamming to Brahms, Miles Davis and (of course) Duke Ellington. More than once during these performances, Chappelle seemed transfixed, and I watched his face relax into a tender smile, as if he were seeing himself in these young people getting ready to make their own bold leaps.

David Montgomery is a staff writer for the magazine.

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