What You Didn't Know About The Allstate Mayhem Commercial Guy

The man who would be Mayhem was born in New York City in 1964. Dean Winters resides in New York today, and much of his career has seen him starring in productions filmed in and around New York, including "Law & Order: Special Victims Unit," "Rescue Me," and "30 Rock." But, despite his close identification with the Big Apple, the five boroughs aren't where Winters spent all of his adolescent years. He has family in Arizona who he would visit often during his childhood, and in the 1970s, his parents decided to make the move permanently. Winters' dad switched jobs and they went out West, but it wasn't exactly a fairytale for the future actor and his brothers.

"Quite frankly, it was a nightmare," Winters told The Arizona Republic in 1999. "It was a cultural blast coming from cement to the desert. I had a tough time adjusting." It didn't help that the school he ended up attending (Brophy College Preparatory Academy in Phoenix) wasn't exactly next door to his new family home in Scottsdale. Winters went on to attend Colorado College, where he studied English. He didn't exactly enjoy the experience. "Mostly, I majored in trying to get the hell out of school," he later admitted. "School and I never seemed to walk hand in hand."

On a morning in June 2009, Winters woke up with a fever and stayed in bed all day. The next morning, he still felt terrible and noticed he'd turned gray, so he went to his doctor's office. That's where he collapsed. "I was turning black, and my whole head was swelling up," he later told Page Six. An ambulance raced Winters to Lenox Hill Hospital, but on the way, his heart stopped — for two and a half minutes. Paramedics revived him, and he wound up spending three weeks in intensive care to recover from a horrific bacterial infection. Over the next year, he spent a total of 95 days in the hospital and endured 10 operations, including the amputation of two toes and half a thumb — he'd developed gangrene during his ordeal.

Winters was too sick to work for a year. Right before he nearly died, he'd filmed a pilot for an ABC show called "Happy Town," and when it was picked up to series, producers replaced him with Steven Weber of "Wings." "People in Los Angeles think I'm dead!" Winters sort-of joked. However, exactly one year and one day after he almost died, his best-known work hit screens when Allstate launched its "Mr. Mayhem" campaign. "It's gonna take more than a finger and a couple of toes to keep me down," he said.

Dean Winters has admitted that his career needed a shot in the arm by the time he was offered the role of Mayhem, but he didn't believe appearing in a commercial campaign was the right move. Of course, he turned out to be wrong: The commercial was a huge hit, and Winters became a recognizable star overnight. "It premiered on June 19, 2010, and I went to visit my mom in Connecticut, so I watched it with her," Winters said during an Esquire interview. "The next day taking the train back into the city, everyone in the train car was looking at me." Soon after that, there was an incident on the subway that introduced Winters to the life of a man with a famous face with a bang.

"I got on the subway and it was the first time I ever felt threatened on the subway," he explained. "This was the next day and all these kids were on the train and they recognized me and started going insane." According to Winters, the attention "hasn't stopped" since then, with people recognizing him out and about in New York on a regular basis. However, the important thing is that he hasn't had a long stretch without work since becoming Mayhem, something he never saw coming. "If someone told me an insurance commercial was going to be the thing [that] resuscitated my career, I would have laughed in your face," he said.

Winters landed his first movie role in the 1997 Mel Gibson/Julia Roberts thriller "Conspiracy Theory." Up to that point, he had primarily paid the bills with a bartending job, which he held literally up until filming was under way. "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 told AV Club. He immediately got a taste of how frustrating the movie business can be. "I had a much bigger part, but it got completely whittled away," Winters claimed. "I spent a lot of time on the set twiddling my thumbs, trying to figure out how I was going to quit the business. It was a tough job!"

Winters actually did try to go back to his old bartending job, and he might have, had he not deliberately burned that bridge. "The owner wouldn't take me back because I told him to go f*** himself when I quit," he recalled. "Because I wanted to make sure when I quit that I wouldn't have a way back in!" He asked anyway ... and was denied. Still, even if he couldn't get his old gig back, he had his first film on his resume and he even managed to strike up a relationship with one of the stars. "I would go to Julia Roberts' trailer, and she and I became friends," Winters said. "I used to walk her dogs for her on the set."

Dean Winters has been in plenty of movies and TV shows, some of which are downright iconic. Yet, he arguably remains best known to millions as Mayhem, the chaos-inducing mascot for Allstate. Insurance isn't the only thing Winters has pitched in his career, though, and decades before he was crashing cars and smashing bars, he was the face of something very different: Colt 45 beer. It's a job he only took because he wasn't finding work on television, but it remains an interesting footnote in his long and winding career. "I've done a few jobs out there for the money and I find those jobs have come back to haunt me," Winters told Esquire in 2011. "I was the only white guy ever cast in a Colt 45 ad."

The actor went on to explain that the makers of Colt 45 were coming under some pressure from the NAACP. The company launched what The New York Times called "aggressive marketing campaigns aimed at minority drinkers" in the 1980s. According to Winters, the backlash against these campaigns is why he was cast. "They had to make a commercial with a white guy, and that was me." The commercial itself has been lost to history, much to the actor's annoyance. "[It] was before the internet, before cell phones," Winters said. "I cannot find this thing."

In a way, Dean Winters was right to be intimidated by all the comedic actors lining up to audition for "30 Rock." It's hard to remember now, after projects like "Brooklyn Nine-Nine," "Rough Night," and of course, Allstate's Mayhem, but in the early 2000s Winters was not seen by many as a "comedy guy." His best known roles at the time were "Oz" and "Law & Order: SVU," which had their moments of gallows humor, but were otherwise as grim as it gets. "30 Rock" transformed his career, and in the years since, Winters has fully given credit to that show's creator, Tina Fey. "Tina's in my top two favorite people in Hollywood," he told Backstage in 2021. "She's always been in my corner."

What was originally meant to be a three-episode stint in the first season became a recurring role, as beeper king Dennis Duffy appeared at least once in each of the show's seven seasons. Since "30 Rock" ended in 2013, Winters and Fey have remained in each other's orbit: In 2019 they reunited for a pair of Allstate ads promoting the insurance company's new Drivewise app, and over the years he has made guest appearances on the Fey-produced comedies "Unbreakable Kimmy Schmidt" and "Girls5Eva." "I'll do anything for Tina," he said to Backstage. "Just to be part of a Tina Fey production — she knows the quality is going to be good, the actors are going to be good, everything is going to be good."

As a young man, Dean Winters wrote himself an acting "bucket list" of all the different kinds of projects he aimed to perform in someday. "I was, like, 'I want to be in a horror film, I want to be in a Western, I want to be in this, I want to be in that,'" he revealed to the AV Club. One item Winters can cross off that list: He's appeared in a horror movie. He played a sleazy businessman mourning his wife and dealing with amnesia in the 2002 direct-to-video release "Hellraiser: Hellseeker."

Sadly, while he got to tick an item off his bucket list, it wasn't exactly a dream come true — Winters didn't have the best time shooting the film. "I took that movie at the last minute, I got to Vancouver, and if there were 120 scenes in the movie, I think I was in 116. And I got sick, like, at the end of the first read-through." Winters wound up being extremely ill for three weeks out of the four-week shoot, which took place in a real psychiatric facility. "I was having nightmares and seeing visions in the hospital," Winters said. "It was just bananas."

An Allstate commercial from March 2023 features Winters once again as Mayhem, here taking the form of "your highly competitive older brother," whose overly aggressive basketball playing turns a friendly pick-up game in the driveway into a potentially costly repair job. The other brother — the one whose garage gets wrecked — is mostly kept in the background as Mayhem hogs both the ball and the scene, but it didn't take long for fans to recognize the actor playing him as Winters' own brother and former "Oz" and "Homicide" co-star Scott Winters.

The two Winters brothers began their on-screen careers at around the same time in the mid-1990s, and Scott, like his younger brother, has played his share of cops and authority figures on shows like "The Dead Zone," "Dexter," and "City on a Hill." But aside from a recurring role on the Netflix renaissance drama "Borgia," his most recognizable role may be one of his earliest, as the Harvard blowhard who gets shown up by Matt Damon in the 1997 drama "Good Will Hunting." 

The scene and its instantly memorable punchline ("How do you like them apples?") was even parodied four years later in Kevin Smith's "Jay and Silent Bob Strike Back," with Damon, co-star and co-writer Ben Affleck, and Winters all reprising their roles. In recent years he has turned his attention to the non-profit foundation Merciful, which he founded alongside wife Jennifer and daughters Faith and Grace.

Dean Winters is a regular at the hallowed grounds of New York's stadiums and arenas, where his unwavering support for his ancestral city's sports teams is well known. He's a frequent visitor to Madison Square Garden, and Winters has been spotted sitting courtside with celebrity friends at New York Knicks games. He's also been seen attending Rangers hockey games, and on Instagram he talked about how sports was a big part of his childhood.

In the post, he recounted the story of how his father took him to his first hockey game when he was just five years old. His long-standing love for the Rangers made it all the more meaningful when he appeared on the jumbotron as a celebrity fan. "Where it may seem trite to few, to be on the Jumbotron is a humbling New York City moment which I couldn't be more grateful for," he said.

In another memorable moment, his role as Mayhem led to him meeting with legendary New York Yankees play-by-play man John Sterling during an appearance on the Boomer & Carton radio show in New York. Sterling even promised to watch Winters in his critically acclaimed CBS drama "Battle Creek," which no doubt made his day.

Before playing Mayhem, Dean Winters was a regular on television, appearing in several big shows. However, hit movies had always eluded him. He had a small role in 2007's "P.S. I Love You," but after becoming the face of Allstate Insurance, more movie roles started coming his way. In 2014, he finally appeared in a bonafide movie classic, taking a major role in the Keanu Reeves action-thriller "John Wick" — he plays Avi, one of the movie's main villains. The right-hand man of criminal kingpin Viggo Tarasov (Michael Nyqvist), Avi has a tough guy exterior but he's a coward underneath.

According to Winters, it was his work in "Oz" that got him the role. "I didn't have a good audition, but the directors, Chad Stahelski and David Leitch, were big 'Oz' fans," Winters told Esquire, meaning he all but had the job the moment he walked through the door. As for Avi, the actor says he liked that it was something new for him. "My character in that I feel is the opposite of what I've done in my career, so it was great making this crooked hedge-fund guy a whiny p***y." Avi meets his end at the hands of John Wick himself, which is why Winters hasn't taken part in any of the sequels.

In 2020, the COVID-19 pandemic shut down movie theaters across the country for months, and when they finally reopened, the industry had sustained damage that would take years to recover from. But the global crisis didn't just impact Hollywood via cinema closures, it essentially ground production to a halt, with the industry shuttered for much of the year. It wasn't until very late in 2020 that any new studio productions went before cameras, and one of the first featured Dean Winters.

Always on the lookout for a movie role, Winters took a part in "Christmas vs. The Walters," an independent holiday movie starring Shawnee Smith ("Saw"), Bruce Dern ("The Hateful Eight"), and Chris Elliott ("Groundhog Day"). When it began filming in November, the pandemic was still raging and vaccines were still weeks away. The production, which took place on Long Island, utilized plenty of safety precautions, including mask-wearing during rehearsal and regular testing for coronavirus among cast and crew.

Making the movie was "challenging," Winters said when he spoke to TV Meg alongside Shawnee Smith. According to Smith, the weather wasn't helping matters. "You can't really rehearse like that," she said. "I mean, you do the best that you can, but all the windows and doors are open for ventilation, and it's November. In November in New York, in Long Island; you're freezing." Despite all the hurdles, the film was completed and got a limited theatrical release the following November.

To say that Dean Winters loves New York City is an understatement. Whether he's out at a sports game or joining the SAG-AFTRA strikes at the Netflix and Warner Bros. Discovery offices in the city, the actor is usually found in the Big Apple. "I never, ever leave New York," he told The Sydney Morning Herald while promoting "Battle Creek," a rare Winters project filmed away from New York. In 2018, Winters made it clear that he still considers New York home: The New York Post confirmed that he had bought a new residence in Manhattan for $3.5 million.

According to the public records cited in the report, Winters purchased a duplex in the Tribeca neighborhood. It's the same area that superstars like Robert De Niro, Jennifer Lopez, and Beyoncé call home, and it even has a so-called "paparazzi-proof" luxury apartment building where the likes of Jake Gyllenhaal, Ryan Reynolds, and Jennifer Lawrence have all lived at one time or another.

As for Winters' Tribeca pad, the two-bedroom, two-level condo has a host of swanky features, including a real wood-burning fireplace and an entertainment area with 12-foot ceilings. "The master bedroom suite features a skylight, a walk-in closet and an ensuite spa-like bathroom with a shower and separate soaking tub," the Post revealed. "A spiral staircase leads to the second level, and showcases a den or home office that opens to the private roof terrace." There's even an entrance that is highlighted for its use as a private art gallery. And, by all accounts, Winters got quite the bargain on the unit, as it was for sale for over $5 million just two years earlier.