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Hyde Park, Woodlawn, South Shore

This South Side Cowboy Has Become A Viral Video Star During Pandemic

"A lot of people from my community have never seen a horse in real life, let alone be on top of the horse," said Adam Hollingsworth, a Woodlawn native who rides as Dreadheadcowboy.

Left: Adam Hollingsworth, who rides as Dreadheadcowboy, with Spirit the horse. Right: Hollingsworth on top of a horse on 71st Street.
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WOODLAWN — Numerous viral videos in recent weeks have shown a cowboy riding through Chicago’s neighborhoods.

That cowboy is Adam Hollingsworth, who rides under the name Dreadheadcowboy. When temperatures rise above 55 degrees, he’s likely to be riding his horse Prince through the streets of Chicago.

He’s been spotted near the courthouse on 26th and California, on 79th Street and on 87th Street on the city’s South Side.

The 33-year-old, who makes his living as a boxer, learned how to ride from his uncle two years ago. He started doing it for attention, but the smiles he’s seen from kids and adults on recent rides have convinced him to do more than just show off his horses.

He’s started a GoFundMe with the goal of teaching Chicago kids how to ride, groom and care for a horse. If his $50,000 goal is met, he’ll take his riding workshops across the Midwest.

“A lot of people from my community have never seen a horse in real life, let alone be on top of the horse,” Hollingsworth said.

Warning: These videos contain explicit language

Taking care of another animal can be therapeutic, he said. He credits his horses for helping to improve his own mental health.

“I’m riding with a purpose now,” Hollingsworth said. “I was down, depressed, at rock bottom in November, December and January. When I started going out to ride my horse, it uplifted me.”

He now lives in Crete, but grew up “a bad little kid” at 62nd Street and Kimbark Avenue in Woodlawn. Until four years ago, the only horses he’d ever seen were at the Bud Billiken Parade or police horses.

Though there’s a thriving community of Black cowboys in Chicago, Hollingsworth prefers to ride solo.

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He went to last year’s High Noon ride in Washington Park with his uncle, who rides as Big Bopper. But the annual gathering of Chicago’s cowboys “wasn’t my element,” he said.

“I got a horse just so I could show the youth something different, show my guys something different,” Hollingsworth said. “They done seen everything. Fancy cars, big houses, people with money … but they’ve never seen one of their homies on a horse.”

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