The Hidden Truth Of The Actor For Allstate's Mayhem Guy

Some actors achieve household name status by getting really good at pretending to be other people in big movies and TV shows, while other performers are of the character actor ilk. The latter can be so good at what they do that they may disappear into a role entirely, with only discerning viewers recognizing them when they pop up on screen, yet remaining largely anonymous. In the middle is a rarefied area occupied by people like Dean Winters. A prolific, workaday actor, he's made an impression playing police officers, tough guys, and miscreants in TV classics like "Law and Order: SVU," "30 Rock," and "Oz," but he's absolutely most famous for portraying the human embodiment of chaos in a string of funny insurance commercials going back a decade and a half.

To TV audiences, Winters is and probably always will be "Mayhem," the sarcastic, gleeful agent of doom who demonstrates everything that can possibly go wrong in life in order to sell customers on the benefits of Allstate insurance packages, including one of the best Super Bowl commercials ever created. Mayhem is just one of the characters that the actor has portrayed with a signature combination of intensity and wit. Here's a look into the professional rise and personal, off-screen life of the man behind the Mayhem, Dean Winters.

While trying to make it as an actor in New York in the 1990s, Dean Winters tended bar to pay the bills. In 1995, he landed his first credited screen role, portraying Tom Marans on three episodes of NBC's police drama "Homicide: Life on the Street." That gig was the result of Winters' job serving drinks, after "Homicide" writer and executive producer Tom Fontana entered Winters' bar late one night. "We had never met before, but he was doing the first season of "Homicide," and he and I became really good friends. He offered me a part for my 30th birthday, and I passed on it. I told him I wasn't ready to be on TV yet, because I was still living downtown and doing theater," Winters told The AV Club. 

Winters eventually accepted that offer and very soon after secured a role in the Julia Roberts film "Conspiracy Theory," one so substantial that he thought he could quit his survival job. "My last night of bartending was Thanksgiving '96, and I started filming that movie either the next day or a couple of days later," he said. But then his part got pared down during filming, and Winters tried to reclaim his old job. "The owner wouldn't take me back because I told him to go f*** himself when I quit. Because I wanted to make sure when I quit that I wouldn't have a way back in!"

Dean Winters woke up one morning in June 2009 running a fever, so he spent the day in bed. The next day, he still felt ill and noticed that his skin had turned a troubling shade of gray. And then his condition deteriorated further. "I went to my doctor's office on Central Park West, where I collapsed. I was turning black, and my whole head was swelling up," Winters recalled to Page Six. During an urgent ambulance trip to Lenox Hill Hospital, Winters technically died as his heart didn't beat for more than two minutes. Revived by paramedics, Winters was placed into the intensive care unit, where he spent three weeks receiving treatment for his medical issues and their source: a severe bacterial infection.

Winters was sent home to continue his recovery, but a month in, gangrene set in. Resuming hospitalization for another 95 days altogether, Winters endured as many as 17 surgeries, including procedures to amputate two toes and part of a thumb, skin grafts, and a reconstruction of his right hand using muscle taken from his forearm. The actor recovered, but he still copes with lasting effects from this period. "I haven't taken a step since 2009 without being in pain," he told Page Six. "I've got neuropathy on, you know, on a whole different level where I can't feel my hands and my feet. But if I stepped on a pebble, it's like I go through the roof."

The odds of one member of a family finding lasting success in show business are slim, let alone three brothers all consistently landing work in film and television. But the three Winters brothers all did, comprising a low-key family dynasty whose members have all worked in some of the most acclaimed television of the past three decades. Dean Winters is best known for his work in multiple "Mayhem" commercials for Allstate, and in a 2023 spot Mayhem engages in an intense, property-destroying game of driveway basketball with his brother. Portraying the sibling of Winters' ad mascot character was his real-life brother, Scott William Winters, a prolific actor who has appeared on dozens of TV shows and played a memorably smug romantic rival to Matt Damon's Will in "Good Will Hunting."

There's a third brother in the Winters family: Bradford Winters, a producer and writer for television since the late 1990s. The first series he worked on was HBO's prison drama "Oz"; he wrote seven episodes of the show that co-starred brother Dean and featured Scott in a recurring capacity. "It's so much f***ing fun," Dean Winters told "Black Book" (via Mister Winters) of working on "Oz" with his family.

Malt liquor is essentially beer with a higher-than-usual alcohol content. Brewers noticed in the 1960s that the product sold particularly well to Black consumers, and so they began to advertise directly to that segment of the population. Ads for malt liquors like Colt 45 appeared in Black culture magazines and on TV shows with predominantly Black casts, featuring Black models and actors. By the 1990s, the perception of malt liquor as a drink for Black people was very entrenched, and public advocates thought the celebration of the beverage in rap videos and commercials dangerously glorified drinking and denigrated Black people.

When the NAACP called out The G. Heileman Brewing Company, the Wisconsin-based producer of Colt 45, the company made exactly one commercial with a white actor: Dean Winters. "The makers of Colt 45, they were being targeted by the NAACP for only playing to the urban crowd, so they had to make a commercial with a white guy, and that was me," Winters explained to Esquire. A cultural and advertising obscurity by intent, the ad may not have survived past the 1990s. "That was before the Internet, before cell phones. I cannot find this thing," Winters said.

Nudity is highly regulated on American television, and while the Federal Communications Commission disallows nudity on ad-supported broadcast television, cable networks like HBO are free to show pretty much whatever they want. That policy has led to some of the biggest scandals to ever hit HBO, but it has also helped make TV history. In 1997, actor Dean Winters joined the original cast of HBO's prison-set series "Oz," portraying incarcerated violent criminal Ryan O'Reily. During a Season One episode, Winters' character experiences serious mental health issues while being held in solitary confinement, and the actor went completely naked for that harrowing scene.

"I was the first male to ever be full-frontal nude on American television," Winters said on "The Artie Lange Show" in 2014. Many HBO shows before and after "Oz" would feature disrobed female actors, but Winters' claim to that particular benchmark appears to be accurate.

If you or someone you know needs help with mental health, please contact the Crisis Text Line by texting HOME to 741741, call the National Alliance on Mental Illness helpline at 1-800-950-NAMI (6264), or visit the National Institute of Mental Health website.

Despite noted runs on numerous major TV series like "Oz," "Rescue Me," "30 Rock," and "Brooklyn Nine-Nine," in addition to his work as Allstate's Mayhem, Dean Winters still has to audition to secure roles in movies and television shows. That generated a number of unpleasant and disappointing experiences for the actor, even if he did wind up landing the gig, such as what happened with "John Wick." "It's funny, I didn't have a good audition, but the directors, Chad Stahelski and David Leitch, were big 'Oz' fans so they were like, 'When you walked in the room you had the job," Winters told Esquire. One of the actor's first auditions ended in an outburst. "I remember the director, while I'm reading and I'm being taped," he told Backstage, "and this guy is in the back on his phone, texting, eating a sandwich. I remember taking my script and throwing it at him, hitting him in the face."

He's also missed out on some big roles in major motion pictures. "I have never been considered for a lead in a studio picture yet, but there were some second and third roles I wanted. I remember I wanted a small role in 'Michael Clayton' playing George Clooney's brother," Winters recalled. "I read for a role in 'Winter's Bone.'"

Along with most other sectors of the American economy, the film and television production industry shut down in March 2020 as part of global efforts to help limit the spread of the COVID-19 virus. By the end of the year, production slowly began to ramp up again, with a small and independent films getting underway with numerous newly adopted safety measures in place, such as social distancing, ventilation, and the use of face masks. 

This became standard operating procedure for most movies and TV shows over the next few years, and actor Dean Winters helped figure out how all of those anti-coronavirus measures would work on a day-to-day basis. Shooting began in November 2020 on the independent holiday feature "Christmas vs. the Walters." "We were one of the first movies to actually shoot during COVID-19," Winters told TV Meg. "It was a real new experience for everybody. So that was the most challenging part."

Dean Winters' talents were needed on only three episodes of "Homicide: Life on the Street," but those appearances spanned across three seasons, making him a recurring presence on the set of the 1990s NBC police show. During his run on the show, Winters developed a friendship with one of the series' main stars, Richard Belzer, an actor turned down by "SNL" who went on to become a huge star. When NBC canceled "Homicide" in 1999, TV producer Dick Wolf asked Belzer to reprise his character, the droll and grizzled Detective John Munch, on his new series "Law and Order: Special Victims Unit." Belzer moved over to the new show only because Wolf agreed to one of his conditions — that he give his friend Winters a part as Munch's partner.

Winters played Detective Brian Cassidy for the first 13 episodes of "Law and Order: SVU," and showed up occasionally as a guest star in 20 more episodes broadcast between 2012 and 2019. Winters' prolonged absence could be an argument for why it's finally time to cancel "Law and Order: SVU."

Dean Winters' troublesome Allstate character Mayhem is similar to his previously most famous role: Dennis Duffy, a sleazy mess of a sometimes boyfriend to Tina Fey's Liz Lemon on the sitcom "30 Rock." Winters showed up to mooch off of Liz and call her a "dummy" in 15 episodes, a long-term gig he almost didn't get because he tried to preemptively remove himself from consideration.

One of the show's directors, Adam Bernstein, previously worked with Winters on "Oz" and recommended him for Dennis, even though he didn't have any prior comedic experience. He still had to try out for the job, however. "I went to the audition for '30 Rock' — I walked in, and there was, like, 30 guys up there reading for my role, and they all — they were the funniest guys in New York City. I'm not going to mention any names, but they were all a bunch of funny guys my age," Winters told The AV Club. He signed in, seized up the competition, and left. "I knew I wasn't going to get the job, and I didn't want to waste their time or my time." 

Later that day, Winters received a call from his agent's assistant, who inquired about the "30 Rock" audition; the actor lied and said it had gone well. Called out on his fib, the agency ordered Winters to return to the audition — if he didn't, they'd drop him as a client. "So I went back," Winters said, and the rest is TV history.

After he nearly died after contracting a bacterial infection and enduring a cardiac arrest in the summer of 2009, Dean Winters thought that his medical ordeal spelled the end of his acting career. "I was told I was never going to walk again," he told the Sioux City Journal. "It was the darkest period of my life." During his months-long recovery that necessitated a hospital stay, Winters was so depressed that a medical professional took a special interest in his situation. "This nurse took me to the children's burn unit. I saw these eight kids with prosthetic legs playing soccer and I thought, 'That's it.' That's the moment when I turned everything around and decided to learn how to walk again."

Just before his illness, Allstate Insurance had asked Winters to portray the personification of mayhem in a television commercial. He initially turned down the job before accepting it when Allstate approached him again, triggering a personal and professional comeback. "When they offered me the commercial, I said no," Winters said on "HuffPost Live." "My smarta** 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.'" The first ad featuring Winters as "Mayhem" debuted in 2010 — followed by more than 115 additional spots.

If you or someone you know needs help with mental health, please contact the Crisis Text Line by texting HOME to 741741, call the National Alliance on Mental Illness helpline at 1-800-950-NAMI (6264), or visit the National Institute of Mental Health website.

In upwards of 115 and counting comedy sketch-oriented advertisements, Dean Winters has portrayed the concept of mayhem as Mayhem, a darkly enthusiastic imp who makes terrible and unexpected things happen to the woefully uninsured. Since 2010, Winters' work as Mayhem has served as the public face of Allstate Insurance, the contemporary vestige of what used to be Sears stores. Winters' broadly comic go-for-broke performance has helped turn around the fortunes of the insurance giant. In the early 21st century, Allstate competitor Progressive signed up huge numbers of younger, potentially long-term insurance customers through the strength of its ad campaign, featuring an exuberant salesperson named Flo. Allstate was struggling with serious ads starring spokesperson Dennis Haysbert. Allstate's ad firm, Leo Burnett Worldwide, set out "to kick Flo's a**," as executive vice president Nina Abnee told "Ad Age."

The Mayhem commercials worked. Within a year, Allstate boasted one of the most recognizable insurance brands in the U.S. And while Allstate has potentially banked billions from Winters' ads, the actor earns a mere $4,750 per performance.