The Reason Jeffrey Dean Morgan Left Supernatural

During his brief stint as John Winchester, Morgan was also appearing on Grey's Anatomy and Weeds. In 2006, he marveled at his good luck in an interview with the Orlando Sentinel. "It's a complete switch, I'll tell you that," he said of balancing three roles at once. "I've been kicking around this business for a long time. Persistence pays off. You kick around long enough, and good things can happen. It's been one heck of a year. I can't complain."

Ultimately, all three of his characters were killed off, but Morgan didn't miss a beat. In 2007, he starred in the romantic film P.S. I Love You alongside Hilary Swank, and by 2009 he had landed the role of the Comedian in Zack Snyder's Watchmen. He continued to work steadily in film and on TV after that, and in 2016, he landed the role of the baseball bat-toting Negan on The Walking Dead. Given how steady his workload remains to this day — and just how big of a show The Walking Dead is — it's surprising he was able to make time for a Supernatural comeback at all, even if it was for only one episode.