Throughout 15 epic seasons, the Winchester brothers have encountered countless villains. From demons and angels to even God himself, the show’s rogue gallery is as diverse as it is terrifying. But who stood out as the most iconic? Let’s take a closer look at the baddies that kept us—and Sam and Dean—on the edge of our seats.
It’s no surprise that Crowley, portrayed by Mark Sheppard, tops our list.
As the King of Hell, Crowley started as a crossroads demon with a quick wit and sharp tongue. His journey from a soul-selling demon to a reluctant ally—and even Dean’s bizarre “friend”—is one of the most unexpected character arcs on television. “Hello, boys!” became his signature line, and his complex relationships with both Sam and Dean made for some of the show’s most memorable moments. His sacrifice in the season 12 finale to save the Winchesters cemented his legacy as the underdog who outlived expectations.
"I guess this is goodbye," he said, in one of the show’s most emotional scenes. Crowley’s mix of humor, menace, and reluctant humanity makes him an unforgettable villain.
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