Why Allstate's Mayhem Commercial Guy Looks So Familiar

Few faces are as recognizable in television advertisements as the stars of insurance commercials. Everyone knows Flo from Progressive, and the Geico Gecko and Aflac Duck were smart branding moves. There's also Jake from State Farm, as well as newer additions like LiMu Emu and Doug from Liberty Mutual. But there's one mascot that continues to come back again and again, and that's Allstate's Mayhem, played to perfection every time by the one and only Dean Winters.

If Winters looks familiar to you, that's because he's been on your screens since the mid-1990s, long before Mayhem's first appearance in the summer of 2010. The New York native has appeared in various feature films and television shows throughout his near-three decade career. What may surprise you is that Mayhem isn't a typical character for Winters — while he's adept at comedy, he's actually best known for his dramatic roles. Here's where you may have seen him in action before.

Dean Winters had been in a few shows and movies before the HBO prison drama "Oz," but this was the actor's big break. Producer Tom Fontana wrote the part of Irish inmate Ryan O'Reily for him after getting to know the up-and-coming actor at a bar. Winters was working there at the time, and the pair hit it off. "When I was a bartender, I was a total hustler," Winters told AV Club. "Like, if you walked out of my bar with cab fare, then I failed, because I would do everything I could to make sure you were broke."

Like many of his former "Oz" castmates, the HBO series was just the start of a bigger career for Winters. Unlike many of the people held in the Oswald State Correctional Facility, Winters' O'Reily is one of the few to make it through the entire series still breathing, though he had a few close calls. Credited for 56 episodes, Winters' "Oz" character is the actor's most prolific role, an exceptional performance that firmly established him in the business.

While "The X-Files" was always the more popular show, in the mid-90s, Fox greenlit a second Chris Carter-helmed series titled "Millennium," which followed former FBI profiler Frank Black (Lance Henriksen) as he meditated on the nature of evil. While the first season primarily saw Frank go up against various serial killers and religious zealots, the show's sophomore year took a more supernatural approach, more akin to the sister series. In the trademark Halloween episode, "The Curse of Frank Black," Dean Winters appears as the ghostly Mr. Crocell, who confronts Frank about his life choices.

Winters' performance here is great. In the flashbacks to Frank's childhood, he plays Crocell as a World War II vet with survivor's guilt, a man whom his neighbors see as something of a spectral figure. Sure enough, by the episode's end, Crocell's ghost appears to Frank, tempting him to give up the fight and succumb to darkness. It's an interesting performance from Winters that plays on his theater roots as an actor. The creatives behind "Millennium" must have liked working with Winters, as they brought the actor back for the following (and final) season to play another character: He appears as the young version of FBI agent Michael Lanyard in the episode "Matryoshka."

After playing smaller parts in movies like "Conspiracy Theory" with Julia Roberts and "Lifebreath" with Luke Perry, Dean Winters headlined a "Hellraiser" sequel that harkens back to the original films. Despite the long-awaited return of Ashley Laurence as Kirsty Cotton, the sixth film, titled "Hellraiser: Hellseeker," was a direct-to-video production that was trashed by critics – it has a 0% rating on Rotten Tomatoes. Dean Winters and his co-stars, especially Sarah-Jane Redmond (who also previously appeared in "Millennium"), weren't the problem here: A poor script and even worse direction sealed the fate of "Hellseeker."

"That was a brutal, brutal job," Winters said of the film years later while speaking to AV Club, noting that he was sick for much of the filming and experiencing nightmarish visions. "But it ended up being a really good experience. I wanted to do a horror film — I'd never done a horror film — but we ended up shooting in a real psychiatric hospital, which completely f***ed with my head." He added that working with Doug Bradley as Pinhead was a dream come true, and although the film is known as a disaster, the actor is happy to have ticked the horror genre off his bucket list.

Every generation seems to get their own version of "The Twilight Zone." While the original Rod Serling-created series ran for five seasons between 1959 and 1964, it eventually spawned a feature film in 1983, a three-season revival from 1985-1989, another season in 2002-2003, and a two-season return in 2019-2020. And that's not including the made-for-TV film from 1994. During the brief one-season stint on the UPN in the early 2000s, Dean Winters made an appearance, popping up in the episode "Future Trade." While Winters doesn't play the episode's main character (Frank Whaley takes that role), his appearance is memorable nonetheless.

Winters plays Gordon, a deadpan sales rep for a corporation named Future Trade, which specializes in switching the lives of its customers. Basically, you pay to switch futures with another person, which can go either way depending on who you switch with. Convincing Whaley's Martin Donner to trade with someone else (in this case, a wealthy man with a trophy wife) proves to be a bit more challenging than most, but Gordon eventually gets Martin to partake. Of course, this being "The Twilight Zone," things don't go as planned, though Winters' character is unaware of Martin's grisly fate.

One of Dean Winters' most famous television roles is Dennis Duffy from "30 Rock." The Tina Fey-led series ran for seven seasons on NBC between 2006 and 2013, and, unlike some of Liz Lemon's other horrible boyfriends, Dennis appeared in every season of the New York-based sitcom. Winters got to try his hand at straight comedy for the first time with "30 Rock," which changed the course of his career. "Next to 'Oz,' that's the best job I've ever had," Winters explained to AV Club after the series ended. "And it was the first time that anybody ever let me be funny. Tina took a real chance in giving me that job."

Unlike many of Winters' more mature roles, "30 Rock" allowed him to revel in immaturity. The show was a major career boost for the actor, who appeared in 15 episodes in total. While most people know him as Mayhem, Dennis "The Beeper King" Duffy is his next most recognizable character, and he has Fey to thank for that. "She didn't have to give me that job, because I had done nothing in my career to prove that I was funny," Winters reflected during his candid AV Club interview. "But she gave me that shot, and it opened up a whole new bunch of doors for me."

If you're a fan of "Law & Order: Special Victims Unit," then you'll no doubt know Dean Winters as Detective Brian Cassidy, who he played in the first 13 episodes of the show. Fans were shocked when Cassidy –– who was the partner of Richard Belzer's John Munch –– decided to leave the SVU in favor of narcotics. So what happened? It turns out that Winters' contract with HBO prevented him from appearing on the NBC series again. He had no choice but to drop "SVU" for "Oz," though Winters always hoped to return to "Law & Order."

Winters eventually did come back over a decade later for the Season 13 finale "Rhodium Nights." This brought him back into the fold and he remained on the cast for the next two seasons, but another contractual situation got in the way: CBS kept him from returning to "SVU" once again in favor of the series "Battle Creek." However, since Season 15, Winters has returned as Cassidy on a handful of occasions. He appeared three times during Season 19 when he was promoted to DA Investigator, as well as in the Season 20 episode "Facing Demons."

Additionally, Winters has appeared throughout the "Law & Order" universe in other roles. His first acting gig was actually as recurring guest character Tom Marans on three episodes of sister show "Homicide: Life on the Street," and he also appeared in a 2008 episode of "Law & Order: Criminal Intent" as dirty cop Mike Stoat.

Dean Winters has played his fair share of cops over the years. While "Rescue Me" is primarily a firefighting drama, the New Yorker appeared as Johnny Gavin, an NYPD detective who just so happens to be the brother of Denis Leary's FDNY firefighter Tommy Gavin. While Johnny is only a recurring character to begin with, his appearances gradually increased and he became a regular fixture on the show — until he was killed off in shocking fashion. After that, Winters made a handful of appearances as Johnny's ghost.

Things often get heated (no pun intended) when Tommy and Johnny are in a room together. They fight over women, and they both believe themselves to be the father of Wyatt Gavin, a major source of conflict in the fourth season. "Rescue Me" was Winters' first big job after "Oz" (he appeared in an impressive 33 episodes in total), though, luckily for him, it wasn't too big a change. Both shows deal with mature and often explicit themes, and Winters plays highly questionable characters.

In 2008, Dean Winters ventured back into the arena of genre shows with "Terminator: The Sarah Connor Chronicles." Appearing in a total of nine episodes, he played Charley Dixon, a paramedic and ex-boyfriend of Sarah Connor (played this time around by future "Game of Thrones" star Lena Headey). Charley is introduced in the pilot as Sarah's latest squeeze, but one that, for the first time since Kyle Reese, she actually loves. Charley considers marrying Sarah and is given John Connor's (Thomas Dekker) blessing to do so. In fact, Charley is the closest thing John has to a father in this world.

When Sarah and John are thrown from the 1990s into the future, everything changes. For the Connors, the trip forward was instantaneous, but for Charley, Sarah and John (whom he loved as his own) were gone for over a decade and presumed dead after a bank explosion. Eventually, Charley (now married) reconciles with Sarah and becomes an uneasy ally in the fight against Skynet. Sadly, Charley is killed near the end of the show's second season, and Fox canceled the show right after. "I loved 'The Sarah Connor Chronicles' and I loved that character," Winters told AV Club. "That was also the first job where I played a really nice guy."

His vast experience playing cops and his proven comedy chops on "30 Rock" made Dean Winters the ideal actor for Detective Keith Pembroke (aka the Vulture) on "Brooklyn Nine-Nine." The Andy Samberg-led series became known for the electric chemistry of its cast across its run, which lasted from 2013 to 2021. Originally on Fox, it moved to NBC for its final three seasons after a surprise cancellation. Winters followed Jake Peralta (Samberg) wherever he went, and even became the Nine-Nine's worst captain at one point. Thankfully, that didn't last forever.

Winters plays the Vulture with the same deadpan gravitas he does Mayhem, and it's easy to see where the two characters might overlap. A foil for Jake and his team, the Vulture (called that because of the way he steals already nearly-solved cases) showed up in a total of nine episodes. Though, frankly, it always felt like he was in the show more, such was the presence that Winters created. Sadly, just like with "Law & Order: SVU," Winters was barred from returning to "Brooklyn Nine-Nine" long-term as a result of his contract with CBS for "Battle Creek," which itself only lasted 13 episodes.

Although best known for shows like "Law & Order: SVU," "30 Rock," "Oz," and "Rescue Me," Dean Winters has been a television staple for a long time, appearing on plenty of other well-known shows over the years. From procedurals like "CSI: Miami" and "New York Undercover" to shows like "Life on Mars" and "American Gods," Winters continues to delight whenever he's on the small screen, even if only for a single episode. If Winters can make an impactful impression in a 20-second Allstate ad, there's no denying that he can excite audiences with some meatier roles on television. And boy, does he have a lot of work under his belt.

Winters starred with Josh Duhamel in the aforementioned "Battle Creek," another notable addition to his television resume (despite being canceled pretty quickly). He also played Tony Silvercreek on HBO's "Divorce," Bobby Luccetti on Amazon Prime's "Wayne," and Jeff Lowe on Peacock's "Joe vs. Carole" mini-series, centering around the pandemic-influenced Joe Exotic phenomenon. More recently, he had a recurring role as Nick in the musical comedy series "Girls5eva" and he played Father Morgan in AMC's France-set thriller "Monsieur Spade." No doubt, there will be plenty more electric roles for Winters down the line.

If none of his TV roles mean anything to you, you may know Dean Winters from several small parts in big movies. Take "John Wick," for instance, where he played the sniveling lawyer Avi, who gets directly in the way of Keanu Reeves' titular assassin. While most of Winters' characters are tough, Avi is the exact opposite. The actor has his time on "Oz" to thank for getting the role, because "John Wick" co-directors Chad Stahelski and David Leitch are big fans. "They were like, 'When you walked in the room you had the job,'" Winters revealed to Esquire. "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."

Winters has played other small parts in well-known movies. He was a bartender in "Teenage Mutant Ninja Turtles: Out of the Shadows," a fun callback to Winters' former occupation, and he played Tom in the romantic comedy "P.S. I Love You." Winters also played federal agent John Valestra in the documentary/drama "Framing John DeLorean," which tells of the true story of the automobile executive's life and his involvement in a controversial CIA sting operation via interviews and re-enactments. Netflix subscribers may know him for his role as bank manager Vince Millen in the 2023 action comedy "The Out-Laws."

No matter what he does in the future, for many people, Dean Winters will always be best known as Mayhem. Winters has starred in over a hundred different Allstate commercials as Mayhem, and some of the best of the bunch get us laughing every time they air. Regardless of how many different roles he plays (a teenage texter, a raccoon, or a lost cell phone ringing in the backseat), Winters' mischievous smile and bandaged face keep us coming back for more. Even if he doesn't convince you to switch to Allstate ("and be better protected from mayhem"), the ads are some of the best in the insurance game — the figures prove it.

According to one case study, Allstate raked in as much as $7.9 billion during the first two fiscal quarters of the Mayhem campaign, which represented a sales jump of almost 5% for the company. That's a great return on investment, and the relationship works both ways — Allstate gets more customers, and Winters' Mayhem character becomes ever-more ingrained in American pop culture as a result. In fact, Winters' swagger and charisma make us wish that Allstate would pull the trigger on a Mayhem feature film. It's unlikely, but we can always dream. Until then, check out the 20 best Allstate Mayhem commercials to get your fix.