“Oz” was Dean Winters’ first long-running acting gig and when it ended in 2003, he was unable to land another role right away. “My first job was on ‘Homicide’ and Tom Fontana wrote the Ryan O’Reily role for me in ‘Oz’ two years later and then after that I thought I punched my ticket and it was going to be easy. Talk about a cold-water plunge. I didn’t work for a year after ‘Oz,'” Winters admitted in a 2015 interview with Esquire. When the Mayhem opportunity came along, he wasn’t interested in it but was finally persuaded after meeting the director. “If someone told me an insurance commercial was going to be the thing that resuscitated my career, I would have laughed in your face,” the actor stated.
Since his Allstate role, which reportedly pays Winters a fortune, he has gone on to star in “Battle Creek” and “John Wick,” as well as several episodes of “Brooklyn Nine-Nine.” However, he didn’t forget that prior to his upward trajectory, Tina Fey took a chance on casting him for “30 Rock,” which helped Winters fuse comedy and drama for his Mayhem character.
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Nicki
