Dean Winters

It’s rare that selling insurance ranks among the funniest or most entertaining topics, but Allstate’s series of "Mayhem" commercials has proven a consistent exception to the rule over its years on the air— in fact, this collection of ads ranks among the most successful campaigns in recent memory. It’s easy to understand why they’ve caught on: combining deadpan humor and violent, Jackass-style set pieces to illustrate the importance of a dependable insurance company, they take something most people actively avoid thinking about and turn it into something viewers actively look forward to seeing between their regularly scheduled programming. If you’ve watched these spots and felt like the guy playing Mayhem seems familiar, you’re right—aside from his steady gig as TV’s most violently abused incentive to buy insurance, he’s popped up in a number of shows and films over the last couple of decades. Here are some surprising facts you didn’t know about Allstate’s Mayhem man, Dean Winters.

He actually died (but he’s feeling much better now)

Dean Winters

One morning in June 2009, Winters awoke with a fever and stayed in bed all day. The next morning, he still felt terrible and noticed he’d turned "the color 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.

He tried to avoid Mayhem

Winters almost didn’t make those Mayhem ads. First off, after his medical nightmare, he had to re-learn how to walk. "I was feeling sorry for myself — I had lost toes and half a thumb and the tip of my nose fell off — and this nurse took me to the children’s burn unit," Winters recalled. "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."

Encouragement came from colleagues, and Denis Leary cast him in Rescue Me. And then Allstate Insurance sought him out to play the Mayhem guy in its huge commercial campaign. But at first Winters turned down what he later called "the best job [he’s] ever had." "When they offered me the commercial, I said no," Winters said on HuffPost Live. "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.’"

A ‘Conspiracy Theory’ believer

Winters landed his first movie role in the 1997 Mel Gibson/Julia Roberts thriller Conspiracy Theory. Up to that point, Winters 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 The A.V. 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. Because I wanted to make sure when I quit that I wouldn’t have a way back in!" He asked anyway…and was denied.

A guy walks into a bar…and hires Dean Winters

Conspiracy Theory wasn’t Winters’ first screen acting gig overall. During the 1995–96 TV season, he had a recurring role as Tom Marans on NBC’s acclaimed police drama Homicide: Life on the Street, which he landed through his connection with Homicide creator and producer Tom Fontana. That friendship started when Fontana, when Homicide was in its first season, walked into Winters’ Upper East Side bar at about 2AM one night. Fontana offered to write a role into the show for Winters, but he passed; as he recalled, "I told him I wasn’t ready to be on TV yet, because I was still living downtown and doing theater." Eventually, he relented. When Fontana moved on to create the searing prison drama Oz for HBO, he wrote the role of Ryan O’Reily specifically for Winters.

Winters isn’t the only guy in his family with an Oz connection. His brother, Scott, is also an actor — he and Dean played brothers on Oz. And then there’s Bradford Winters, who served on the Oz writing staff.

He’s raising a ruckus up and down the dial

Shooting a string of 30-second TV commercials is Dean Winters’ most widely known gig, but it leaves him enough time to do lots of acting in movies and on TV shows, where he often plays street-smart tough guys and cops. Since the Mayhem campaign began in 2010, Winters has surfaced on sitcoms like Up All Night (well cast as the brother of Will Arnett’s character), Brooklyn Nine-Nine (a recurring role as a hotshot detective known as "The Vulture"), Divorce (as a foul-mouthed divorce lawyer), and Unbreakable Kimmy Schmidt (as the voice of a cop bunny in a police drama called Bunny and Kitty). In addition to his recurring roles on 30 Rock, Rescue Me, and Law & Order: SVU, Winters starred on Battle Creek, a short-lived CBS crime dramedy co-created by Breaking Bad‘s Vince Gilligan. Winters has also appeared in films like The Devil You Know and John Wick.

Only a dummy wouldn’t audition for ’30 Rock’

For viewers of the Tina Fey sitcom 30 Rock, Winters will always be Dennis Duffy, Liz Lemon’s arrogant, sleazy, odious, pager-selling, on-again, off-again boyfriend. Duffy’s many quirks — including his use of "dummy" as a nickname for Liz — made him a fan favorite, but he almost didn’t get the gig.

"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," Winters later said. "I’m not going to mention any names, but they were all a bunch of funny guys my age." Faced with that level of talented competition, Winters bolted.

Later on, his agent’s assistant called to ask how his audition went. Winters lied and said "it went good." The assistant called him out. "He said, ‘Really? That’s interesting. Because they’re waiting for you. They said they haven’t seen you yet.’" The agency also issued an ultimatum: Go back to the audition, or they’d drop him as a client. Needless to say, Winters went back — and got the gig.

He had a horror-able horror movie experience

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 later recalled.

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. It wasn’t necessarily a dream come true, however. In fact, Winters didn’t have the best time shooting the movie.

"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, but one bright spot was that the film was shot in a real psychiatric facility. "I was having nightmares and seeing visions in the hospital," Winters said. "It was just bananas."

He’s been in and out of the criminal justice system (on TV)

During his time on Homicide, Dean Winters developed a friendship with co-star Richard Belzer, who portrayed sardonic detective John Munch. That show ended in 1999, right around the time Dick Wolf was casting for Law & Order: SVU, a spinoff of his show Law & Order. He wanted Belzer to reprise his role as Munch, and Belzer said he would under the condition that Winters portray his partner in the NYPD sex crimes division. Wolf complied, and Winters got the role of Det. Brian Cassidy. Unfortunately, due to his commitments to Oz, Winters had to leave SVU after just 13 episodes. (They wrote him out by explaining that Cassidy grew overwhelmed with the sick, sad world of investigating rapes and murders, and he transferred to elsewhere in the NYPD.)

After years of feeling like he had unfinished SVU business, Winters finally returned for the Season 13 finale in 2012 and subsequently remained part of the recurring cast.

Allstate was in good hands with Dean Winters

The Leo Burnett advertising agency conceived the Mayhem ads, and in 2011, Burnett executive vice president Nina Abnee told Ad Age that one of their inspirations was "to kick Flo’s ass." She’s speaking about Allstate rival Progressive’s extremely popular advertising mascot. Thanks in part to the Flo ads, Allstate’s market share dropped for two straight years. Also not helping: the company’s previous sober, conservative ads featuring 24 actor Dennis Haysbert calmly and seriously reminding TV viewers of the importance of insurance. Progressive and Geico wooed a younger audience with fun, funny, and memorable commercials emphasizing their product’s low cost.

The Mayhem campaign reversed Allstate’s fortunes with Winters’ character and an emphasis on value over price. (Mayhem frequently belittles "cut-rate" insurance and the fools who buy it.) In 2011, 502 Americans were surveyed on 11 insurance company ad campaigns. After the Geico Gecko and Progressive’s Flo, Allstate had the most correctly identified ads, thanks to Mayhem. Considering that the Geico and Progressive characters had been seen on TV for years, and Mayhem had only been around for months, that’s some remarkably quick-setting brand awareness.