About the artist:

Sir Shadow is one of six men who are the final residents of the Whitehouse Hotel. The crumbling four-story building is one of the last of the cheap single-room-occupancy hotels that lined the Bowery a century ago alongside brothels and saloons and defined the area as a symbol of urban despair. While rooms across the street at the Bowery Hotel cost around $400 a night, the men pay no more than $8.50 for their cramped cubicles, though they pretty much have the run of the place.

As Sir Shadow hums for inspiration, his slender hand strikes a sketchpad with a silver marker and swirls deliriously, never leaving the page, as though he were signing a signature. The elegant silhouette, formed with one continuous line, depicts a saxophone player. He blurs through more: a jazz ensemble featuring trumpet and upright bass; a drummer in the flurry of a solo. His musicians are faceless abstractions.

“I’m a doctor and this is the medication for my patients,” he said one afternoon. “My medicine is positivity. Every line is based on what’s in my heart.”

Sir Shadow arrived at the Whitehouse Hotel around 1995, and he has become a kind of Bowery folk hero since then. At 6-foot-4, he sleeps diagonally to fit into his windowless cubicle. Rarely without his fedora, he gets around on a red electric scooter and draws his blues and jazz musicians across the neighborhood. He calls his one-line style Flowetry, which can be found in the calendars he sells. Quincy Jones, Lauryn Hill, and Diana Ross are said to be fans.

But his masterpiece might be the Whitehouse Hotel itself. Nearly every hallway and boarding room contains a Sir Shadow mural. Even the keys behind the reception desk are marked with his musical silhouettes.

“This building is my canvas,” he said. “These drawings are my warriors. They bring me my peace.”

The artist was born Thomas Allen Paxton in 1949, and he grew up in Jamaica, Queens. He was raised in a sprawling housing project, and he was an artistic child who wrote poetry about life in his neighborhood. He dropped out of Jamaica High School. He declined to discuss his family.

In the 1970s, he told me, he heard about the countercultural movement in San Francisco, and he boarded a cross-country bus.

He instantly embraced the city’s vibrant creative energy and resolved to stay there. He started sleeping on the beach, hanging out with artists, and devoting himself to his poetry. His idyll ended when he heard that his brother died in Queens. “He died for some stupid reason on the street,” he said. “I tried to show him the way but he wanted to be tough and do drugs. Prison changed him. That was hard for me.”

The tragedy triggered a spiritual awakening. “I got the calling after that,” he said. “I realized my mission is to spread positivity through my art. I couldn’t help my brother, but maybe I can help others with my energy.”

He also retired his birth name, a topic he avoided for weeks until we visited a facility in Harlem where he archives his work, and I noticed a label attached to his unit: “Thomas Paxton.” He was brief when I asked about it. “That’s for legal things,” he said. He visibly winced when a receptionist at the storage space addressed him as “Mr. Paxton.” Reluctantly, he offered: “People always ask me about the name my mother gave me. I say, ‘She gave me a name. Then I picked another name.’ Everything that’s real in life has a shadow. And I’m dealing with the shadow of us all.”

He soon returned to New York and he was homeless through the 1980s. He said he lived in subway tunnels and wrote his poetry on underground walls. At the height of the crack epidemic, he served a short sentence in prison for larceny. He insists he was wrongly accused and calls this period his “kidnapping.” Idling in his cell, he kept writing.

“One day I read my poetry out loud,” he said. “Then everyone wanted to hear more.” He recounted how his writings inspired inmates, and they started trading cigarette packs for his poems. Guards privately asked him to critique their own artwork. “I was touching people, and they were touching me,” he said. “They had to kick me out of that prison. I had more work to do.”

After his release, he shed his past, and sobriety became a theme of his poetry. Some years later, while studying for the GED, he suddenly felt compelled to draw in the margins of his coursework: long, flowing lines. “The gift discovered me,” he said. “The line happens and I start to feed it. People say I draw fast but each line has taken me my whole life.”

His metamorphosis complete, Sir Shadow started falling into the city’s black arts scene in the 1990s. His art hung in the homes of Isaac Hayes, Oprah Winfrey and Whitney Houston, according to The New York Amsterdam News, and it was displayed at soul food institutions like Sylvia’s and Londel’s in Harlem. The choreographer Rod Rodgers let him sketch dancers at his company in the East Village, and he designed the art for Gil Scott-Heron’s album “Spirits,” in 1994. “He was my brother,” Sir Shadow said. “We used to talk philosophical.”

- Excerpts from "Sir Shadow, Maestro of the Last of the Bowery Flophouses" by Alex Vadukul for the New York Times, Dec. 28, 2018