Often referred to as The Allstate Mayhem Guy, Dean Winters has built a lucrative career out of causing chuckle-worthy chaos to property in his long-running ad campaign for Allstate Insurance, which has featured him as everything from an attic-destroying raccoon to an emotionally compromised teenaged driver. Since 2010, Winters has ubiquitously popped up on TV screens and on the internet playfully promoting the insurance company that offers coverage for big-ticket items like homes and cars, making him a household name like Flo from the similarly memorable Progressive commercials. In fact, the Allstate ads are so compelling that sometimes people forget Winters is an established actor with an impressive resume — and Winters is okay with that.
While some actors might be bitter about being best-known for commercials, Winters is well aware that he’s lucky to have been afforded such regular work in an industry that can be unstable and unforgiving. When he sat down for an interview with CBS Sunday Morning, the New York native said that while he found it tiresome at first, he’s now happy to be associated with his commercial role because it’s given him security, freely admitting that the ads help him pay the bills and live the lifestyle that he wants. He even went as far as calling the ad campaign “the greatest thing that ever happened” to him. Because who wouldn’t want to be remembered as the guy who earned a fortune pretending to be a vengeful cat riding a Roomba and knocking over lit candles?
Winters has been in several big films and TV shows
Of course, while Dean Winters doesn’t mind being best known for being The Allstate Mayhem Guy, he still deserves recognition for his other roles in film and television. From his breakout role as Ryan O’Reilly on the game-changing HBO series “Oz” to his recent turn as the no-nonsense cop Detective Higgins in the Spike Lee film “Highest 2 Lowest,” Winters has played numerous characters that stand out from his long career. “Law & Order” fans will recognize him as Brian Cassidy, who appeared in the first ever episode of the show and more recently popped up in the Season 27 premiere.
A lot of people forget that Winters was in the hit Keanu Reeves revenge flick “John Wick.” He plays Avi, a counselor and close friend of Russian mob boss Viggo Tarasov. Prior to that, he popped up as Tom in the rom-com “P.S. I Love You.” His other feature films include “The Devil You Know,” “Rough Night,” “After Everything,” “Father of the Year,” “Framing John DeLorean,” “Lost Girls,” and “The Out-Laws.”
Away from the Allstate commercials and “Oz,” Winters is probably best-known for his work in TV comedies, “30 Rock” in particular. He played Dennis Duffy (the on-again, off-again boyfriend of Tina Fey’s Liz Lemon) in over a dozen episodes of the hit sitcom. He credits Fey and “30 Rock” for helping restart his career after a bout of illness that almost killed him — away from the cameras, Dean Winters has actually had a tragic life.