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Meet The ‘Dreadhead Cowboy’, Chicago’s Inner-City Horserider

Colby Smith Colby Smith

Meet The ‘Dreadhead Cowboy’, Chicago’s Inner-City Horserider

The rider has been spotted galloping through the Chicago’s streets on his steeds.

As the city slowly makes it way back to some semblance of its pre-COVID-19 self, there are some that are eager for a return to normality, then, there are some who are embracing the new abnormal.

Case and point: Adam Hollingsworth AKA the Dreadhead Cowboy. You’ve probably seen him in a number of viral videos: either galloping down 79th, dancing on top of his stead, or taking his horse through the McDonald’s drive-thru.

The Chicago-born Hollingsworth saw his first horse only 4 years ago when 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.”

Soon after, with the help of his uncle the 33-year-old got a horse and soon learned how to ride — giving him a sense of pride. One day he took his horse Price for a spin around the community, and after seeing the joyous reaction of all that saw, he continued to do so.

“Not only were the kids excited but the adults as well because they identified they’ve never seen a live horse either. I started allowing the kids to ride my horse and families to take pictures with my horse. I received a lot of positive feed back from people asking if I could come to their area after seeing me on multiple people social media,” he said.

After getting such a positive reaction from the public, Hollingsworth decided to keep the positivity going. With the city in lockdown, and most people staying at home, we thought he’d continue riding in order to bring a little joy to their days. On May 12, he uploaded his first video to a new Youtube account, which he proclaimed his mission:

“The one-and-only Dreadhead Cowboy bringing to y’all a new flavor while I give y’all a tour of my city — the inner city — show you that it ain’t bad like everybody makes it out to be. I’m bringing positive back to the city,” he said.

Hollingsworth was previously an exotic dancer. After losing the job due to the pandemic, he has had more time to ride around city. Before coursing out his trot with his favorite horse, Prince, Hollingsworth takes requests from social media, and will venture those neighborhoods if the weather is nice.

“They love me out there,” said Hollingsworth. “It warms my heart when I see kids smiling, laughing.”

When asked about the name, “Dreadhead Cowboy,” Hollingsworth said: 

“If I’m going to call myself a cowboy,“I gotta put the hood in it, so I put the ‘Dreadhead Cowboy.’ So basically, I’m from the hood and I’m a cowboy.”

See this: City moves to ban horse-drawn carriages beginning next year. 

[Featured image via The Urban Cowboy on Facebook]