Ray Billingsley didn’t much like his second-floor Harlem home on Bradhurst Avenue back then. It was affordable — this being the mid-’80s — but he felt isolated, and he knew crime was a threat: “One evening while in bed with the window open, I actually heard three guys planning on burglarizing my apartment.”

Yet this setting was also where, later that night after going to bed, Billingsley drew inspiration. He awoke with a creative burst. “I had a vision of these two kids. I sketched them down in the dark and went back to sleep. That morning, I found the first images of Curtis and Barry.”

There they were, two cartoon brothers — the taller one wearing Curtis’s signature ball cap, the shorter one in suspenders. With minimal line work, he had rendered his future.

In October 1988, King Features launched Billingsley’s comic strip “Curtis,” centering on the 11-year-old title character and brother Barry, and featuring a predominantly Black cast, which was rare in syndicated comics of the era. The family strip soon proved popular with millions of readers; today, “Curtis” has about 220 print clients and 300 digital clients, according to King.

Thirty-three years later, Billingsley smiles into his computer’s camera as he records an acceptance speech from his Stamford, Conn., home. “I never thought I’d see this day,” he says last month, pausing as he feels the moment. He recalls later by phone: “I was on the verge of tears.”

Billingsley has just won the Reuben Award for outstanding cartoonist of the year. It is the 75th year of the National Cartoonists Society’s peer-voted prize — whose legendary recipients include Charles Schulz, Matt Groening, Rube Goldberg and Roz Chast — but 2021 marks the first time that it has been won by a Black creator, according to comics historians. “This has been a huge step for me, as well as a [huge] step for the NCS,” Billingsley says into the camera, adding: “This has been a very long journey, and I have literally lived my life on a deadline.”

Billingsley, 64, has spent more than a half-century at the drawing board, having turned professional at age 12. He grew up devouring all types of humor and became very aware of such pioneering mid-century Black cartoonists as Morrie Turner (creator of “Wee Pals”), Ted Shearer (“Quincy”) and Brumsic Brandon Jr. (“Luther”).

“It’s been Ray — alone — who has bridged the gap between the first Black nationally syndicated newspaper cartoonists in the [mainstream] White press in the ’60s and ’70s to the current lot,” says cartoonist Barbara Brandon-Croft (“Where I’m Coming From”), daughter of Brandon Jr. and the first African American woman to be nationally syndicated to mainstream newspapers. Such strips as “JumpStart,” “Mama’s Boyz” and “The Boondocks” followed Billingsley’s syndication debut.

Jerry Craft, the “Mama’s Boyz” creator and best-selling “New Kid” graphic novelist, says a critique session with Billingsley was career-changing: “It helped me get to the next level. My work just didn’t look fun, he pointed out. … After a few hours, I headed home with a new outlook on how I wanted my work to evolve, and have never looked back.”

Billingsley first achieved major syndication at the dawn of the ‘80s with a strip, titled “Lookin’ Fine,” that featured Black characters who, like their creator, were in their 20s. The cartoonist soon realized: “I knew I was going to be in trouble.”

Billingsley had studied classic, sometimes-political strips, such as “Li’l Abner” and “Pogo,” and he sought to offer commentary in “Lookin’ Fine.” “There were things I wanted to say — I was very political at the time.” But a sticking point was the weight of his words when such dialogue was uttered by adult characters: “It makes the messages a little stronger than if an 11-year-old says it.”

Another issue: “I had editors who didn’t understand the Black family at all.” They suggested he introduce a new character — perhaps his strip’s family could adopt a White child? He ultimately decided to walk away from the feature in 1982.

Returning to syndication six years later, Billingsley found the sweet spot with “Curtis.” Through the lens of the Wilkins family, whose members live in a brownstone in an unspecified city, the cartoonist could mine his own childhood for humor while also thoughtfully addressing such serious issues as smoking, drug addiction, bullying and covid-19.

“He’s always asking what he can do to push comics — and ‘Curtis’ — further, and to bring contemporary issues to his readers with humor and heart,” Tea Fougner, the editorial director of comics at King, says by email. “In 2020, he doubled down on showing the way the covid-19 pandemic impacted the lives of middle-schoolers and their parents, the frustration and isolation kids felt and the scary experience of uncertainty of a beloved adult and role model falling ill. He does all of this while continuing to tell a uniquely African American story about an ordinary family doing their best through extraordinary times.”

Billingsley felt compelled to weave pandemic story lines into “Curtis” in ways that were relatable for young readers. “I think either a lot of cartoonists were afraid of doing it, or they just didn’t have ideas to support, but I decided to put myself out there,” says the artist, who drew strips about virtual learning, social distancing in school and a beloved teacher who contracted the coronavirus.

The educator who was hospitalized and recovered is the crucial “Curtis” figure Mrs. Nelson, whom Billingsley created in homage to the real-life third-grade teacher who first spotted his artistic talent.

Billingsley was born in the Wake Forest area of North Carolina, and his family moved to Harlem by the time he started school. He began to emulate his elder brother, who liked to draw; young Ray soon doodled on most everything, including the margins of his homework. He won an art contest after encouragement from the teacher surnamed Nelson, and at age 12, he was discovered by Kids, a ‘70s children magazine that hired him as an illustrator and graphic artist.

“That’s when I knew life was going to be different,” he says. Teachers and classmates noted his work, which drew sometimes uncomfortable attention to himself. “I wound up becoming sort of quiet about it.”

Each weekday, the magazine would send a car to Harlem to pick up the kid cartoonist, who worked four-hour shifts after school. Billingsley says he missed out on many social activities and sports — the job “started to separate me from kids” who “had a chance to lead completely normal lives” — yet he loved the work, which continued until he was 18, and liked the steady income.

Billingsley graduated from the High School of Music and Art in Manhattan and then the School of Visual Arts. He started interning at Walt Disney Studios in 1979, but left to launch “Lookin’ Fine” before freelancing in various areas of illustration and design.

The creation of “Curtis,” though, allowed him to channel so many of his youthful experiences. Two of the female classmates in Curtis’s orbit — Michelle and Chutney — were based on real people from his life.

With the strip, he also created a close and communicative bond between father and son. “The relationship between Curtis and his father is actually the relationship I wish I’d had,” Billingsley says. “I couldn’t talk to my father. He was there but didn’t have time for me.” (They reconciled shortly before his father died of leukemia in 1990.)

Billingsley instead found a father figure in Mort Walker, the “Beetle Bailey” creator who became a mentor and Connecticut neighbor. He also received encouragement from Schulz, the “Peanuts” creator, and advice from another late cartooning legend, Will Eisner.

It was Walker and Schulz, in fact, who assured Billingsley for years that awards would come his way — even as he held out hope for book and animation deals that never materialized. “They used to tell me: ‘You’re going to win the Reuben one day.’ ” Years went by, and hope faded into resignation. Billingsley takes a breath:

“That made the win more overwhelming.”

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