Why Allstate Mayhem Actor Dean Winters Looks So Familiar

There's the cheery Flo from Progressive, reliable Jake from State Farm, and then there's the troublesome, accident-inducing Mayhem for Allstate, played by Dean Winters. The character was introduced in 2010 and Winters has since starred in over 100 Allstate commercials, which almost didn't happen seeing as he turned down the role initially. "My mom calls me Mayhem. When they offered me the commercial, I said no. My smartass remark was that I became an actor so I wouldn't have to put on a suit and sell insurance. And then my agent slapped me around and said, 'Come on, get real,'" he shared with HuffPost in 2015.

We can't imagine anyone else playing Mayhem other than Winters and fans have probably placed him in other roles where he plays similar nefarious characters. Before his Mayhem role, the actor became known for his line, "Hey, dummy" in "30 Rock" as Liz Lemon's boyfriend, and as Ryan O'Reily in HBO's "Oz." While Winters is now a recognizable face in Hollywood due to his deep voice and swagger, being an actor hasn't always come easy to him, and starring as Mayhem revived his flailing career.

"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.

Before starring as Mayhem in the Allstate commercials, Dean Winters had a familiar face but was not a household name. "It definitely put my face on the map more than it was. A lot of people in the industry knew who I was, but outside of the industry, it was like, 'There's that guy from that show,' he shared with Backstage in 2021. He added, "I feel very comfortable going back and forth between comedy and drama, which has been a gift in that, when Tina Fey cast me on '30 Rock,' I didn't see that coming. I really had been known as a drama guy before that. Getting the job on '30 Rock' opened up a whole new world for me." Of course, years later when Fey invited him to star in "Girls5eva," he couldn't turn it down. "I'll do anything for Tina," Winters declared.

In 2010, the actor revealed that he feels further indebted to Fey after she supported him following a 2009 health scare, which saw him going into cardiac arrest in the back of an ambulance. After his hospital stay, Fey brought him back to "30 Rock." He shared (via NBC), "When I was going through a really hard time she pulled me out, and I have a debt of gratitude to her I'm not sure I can ever repay."