Who’s That Man Riding A Horse On The Streets Of Chicago? The Dreadhead Cowboy.

Chicago dreadhead cowboy Adam Hollingsworth
Adam Hollingsworth, known as the dreadhead cowboy, takes a ride on his favorite horse, Prince, outside of the Cook County Criminal Courthouse at 26th Street and California Avenue on May 12. Hollingsworth has gained notoriety for riding his horses through Chicago neighborhoods during the COVID-19 pandemic. María Inés Zamudio / WBEZ News
Chicago dreadhead cowboy Adam Hollingsworth
Adam Hollingsworth, known as the dreadhead cowboy, takes a ride on his favorite horse, Prince, outside of the Cook County Criminal Courthouse at 26th Street and California Avenue on May 12. Hollingsworth has gained notoriety for riding his horses through Chicago neighborhoods during the COVID-19 pandemic. María Inés Zamudio / WBEZ News

Who’s That Man Riding A Horse On The Streets Of Chicago? The Dreadhead Cowboy.

On a recent sunny Thursday afternoon, Adam Hollingsworth rode his horse in Chicago’s Roseland neighborhood.

Hollingsworth held his iPhone and recorded himself — and everyone’s reactions to him and his horse, Bella. A group of people gathered around and asked questions, and he encouraged them to take photos and videos.

He’s better known as the Dreadhead Cowboy.

A woman yelled that she’d seen him on TV. Hollingsworth laughed and said it was actually a popular social media account, WorldStarHipHop.

The Dreadhead Cowboy is an entertainer at heart and loves the attention. And now that the weather is warming up, Chicagoans will start seeing him more often, riding his horse throughout the city.

He’s become a little bit of a local celebrity on social media. People see him riding around, take his photos and share them. Some have even made memes.

He started riding his horse last summer, but as Chicagoans remain under lockdown during the coronavirus pandemic, this modern day cowboy is riding more often.

“I ain’t going to say I don’t like attention. Everybody loves attention, that was one of the reasons I started doing it,” Hollingsworth said. “But as I started doing it more, I started seeing the kids like it. … They love it.”

And now, he said, he loves making people smile during the pandemic. He said he checks the weather and, if it’s warm enough for his horse, he goes on social media to ask where they want him to ride. He picks a neighborhood and later documents all his rides on social media. And his images and videos are popular.

The 33-year-old father of four has more time to ride because he said he lost his job as an exotic dancer. “It’s bringing something different to the community, and I start liking that it brings happiness to a lot of people,” Hollingsworth said.

Dreadhead Cowboy
Adam Hollingsworth on his favorite horse, Prince, near the Cook County Jail on May 12. María Inés Zamudio / WBEZ News

This week, Hollingsworth rode around Cook County Jail in Chicago’s Little Village neighborhood. During his ride, he said he spent 18 months in jail. He was charged with possession of a firearm and possession of a stolen motor vehicle in 2006. He was a teenager then and said he was wrongfully charged.

He said he rode around the jail for “all the innocent people” inside the county jail.

Hollingsworth, who grew up on Chicago’s East Side, didn’t grow up around horses. He fell in love with horses four years ago and started this new adventure with his uncle. “I was at his job one day, and we was talking about doing something different, he said we should get some horses,” Hollingsworth said.

His uncle did just that, and it allowed Hollingsworth to interact with a horse for the first time. He said his connection with the horse was immediate. He knew he wanted a horse, so his uncle helped him get one.

And as his connection with the horses grew stronger, so did his bond with his uncle. They went from talking a few times a year to speaking a few times a day. Hollingsworth said his uncle has become like a father to him. “Anytime I have life problems, I call him and he’ll tell me what’s going on. He’ll be real with me,” he said. “He ain’t sugarcoating it. He’s going to be 100 with me, blunt.”

Hollingsworth now has four horses and a pony.

“Every horse has their own personality. You just have to pay attention to it,” he said. “You have to spend time with a horse to see the personality.”

Hollingsworth’s favorite horse is Prince, whose personality is especially useful during his rides through the city. “If a car come past and blow their horn, the horse won’t jump or anything like that,” he said.

As he rides Prince through the city, he said he wants to share his love for horses with other Chicagoans. They love me out there,” he said. “It warms my heart when I see kids smiling, laughing.”

And when asked if he’s concerned about being out during this pandemic, Hollingsworth noted that it’s always dangerous to leave the house as a black man living in Chicago. As for the threat of COVID-19, he said he’s six feet apart when he’s up on the horse.

María Inés Zamudio is a reporter for WBEZ’s Race, Class and Communities desk. Follow her @mizamudio.