Authorities are investigating a fatal shooting that claimed the life of Chicago’s PolaBear Red Filmz videographer Troy Hollingsworth, who is also the influencer Dreadhead Cowboy’s brother, late last night. The Cook County Medical Examiner confirmed that Hollingsworth was the victim after he was pronounced dead following the incident.
According to the Chicago Suntimes, around 9:17pm on Sunday, Chicago Police responded to reports of a person shot at 118th Pl. and Michigan. When they arrived, they found the 37-year-old inside a parked car with multiple gunshots to the body. He was pronounced dead on scene.
CPD says Troy was sitting in his car when an unknown person approached and fired multiple shots at him before fleeing the scene.
The investigation remains active as detectives work to gather evidence and speak with witnesses. Officials are urging anyone who may have seen or heard anything related to the shooting to come forward.
In Chicago’s ever-growing creative scene, Troy has become a trusted name behind the camera. A professional photographer and cameraman with PolaBear Red Filmz, Troy was known for capturing sharp visuals that bring stories to life across music, events, and media projects throughout the city.
With a keen eye for detail and a strong understanding of Chicago’s culture, Troy’s work consistently reflected authenticity and quality. From high-energy shoots to intimate moments, his ability to adapt and deliver has helped solidify PolaBear Red Filmz as a respected presence in the local visual space. He will forever be remembered.
