What To Know About Allstate Mayhem Commercial Actor, Dean Winters

You may not fully recognize Dean Winters without scrapes and bandages covering his pretty face, or disheveled locks spiking up as he wreaks havoc on everyday situations. With them, he's Mayhem, the black-suited character featured in a host of commercials for the insurance company Allstate. After initially turning down the role multiple times, Winters made his ad debut in 2010 and has filmed more than 100 commercials for the brand in the years since. 

But you won't just see the actor in 15- or 30-second increments — the native New Yorker also has a prolific career in both TV and film. He starred in "Oz," "Rescue Me," "30 Rock," and has had recurring roles in "Law & Order: Special Victims Unit," "Girls5Eva," and "Brooklyn Nine-Nine." On the big screen, "John Wick" and "P.S. I Love You" are included on his resume.

Here's what you need to know about some of those credits: In one, he has strong family ties and a lack of wardrobe. For two of them, a mean-girl mentor was involved. 

Before Dean Winters turned into Mayhem, he was the Beeper King of New York City. The actor joined the cast of the TV series "30 Rock" in 2006, playing Dennis Duffy, one of Liz Lemon's legendary boyfriends. He and the show's creator Tina Fey (who also played Lemon) hung out for over a dozen episodes over the course of the show's run, with Winters appearing in at least one episode every season. However, even though Liz and Dennis didn't live happily ever after, Winters and Fey kept their friendship going.

In 2019, the two stars flipped roles, with Fey coming to hang out in Winters' Mayhem territory; the duo appeared together in two Allstate commercials. They then joined paths again in 2021 when Winters was cast as Nick in the Peacock original series "Girls5Eva," with Fey as one of the executive producers. 

"Tina's in my top two favorite people in Hollywood," Winters told Backstage about their relationship. "I tried to repay the favor: I brought her into the Mayhem world. Then when 'Girls5Eva' came around, it was a no-brainer. I'll do anything for Tina."

Mayhem and beepers aside, Dean Winters actually has another role he considers a personal favorite more than any other, that of Ryan O'Reily in the HBO series "Oz." Debuting in 1997, it was one the cable network's first big drama series, and a show Winters still feels a kinship with — literally. 

Not only was it his first regular acting gig, but the series played host to multiple members of Winters' family. Playing his brother, Cyril, on "Oz" was none other than the star's real-life sibling, Scott Winters (above right). Behind the camera, his other brother Bradford Winters (above, middle) was one of the writers on the show. To complete the sibling connection, his sister Blair Winters married one of the executive producers. It's no wonder the actor labeled it one of his most favorite roles. "'Oz' is the closest to my heart," he admitted in a behind-the-scenes interview for "The Arte Lange Show."

Then, of course, there's Winters' claim to fame, courtesy of the HBO series. "I was the first male to ever be full-frontal nude on American television," he shared on air on "The Arte Lange Show."