The Allstate Mayhem Commercial Guy’s 5 Best Movie And TV Roles, Ranked

Despite having a substantial acting resume under his belt, Dean Winters is still best known as Mayhem from the eminently rankable Allstate Insurance commercials. That’s where he warns viewers about absurd-yet-possible worst-case scenarios that might happen, in order to encourage them to buy insurance. From scenarios about being a disastrous raccoon to being an unaware teenage girl, Winters drolly unleashes chaos on unsuspecting drivers and homeowners in the ads, before providing the closing kicker where he says, “Be better protected from mayhem, like me.”

Winters has been starring in the successful ad campaign since 2010, becoming a household fixture on the level of Flo from the Progressive Insurance ads. But while this role may take center stage for him these days, his IMDb page is filled with high-profile gigs on TV shows like “Law & Order: Special Victims Unit,” and in movies like Spike Lee’s “Highest to Lowest.”

So, if you’ve ever wondered where you’ve seen Winters before — or want to check out more of his work — we’ve got you covered with this list of his five best roles. Outside of his famous “Allstate Mayhem Guy,” of course.

Yes, Dean Winters is a bona fide, card-carrying member of the expansive “John Wick” world, portraying the villainous mob crony Avi in the original 2014 film that kicked off a wildly popular film franchise. As a close friend of and legal assistant to Russian crime lord Viggo Tarasov (Michael Nyqvist), Avi plays an integral part when it comes to instigating the blood-fueled action in the first “John Wick” film, when he personally sends henchmen on the hunt to kill John Wick (Keanu Reeves). Of course, in the end, Avi personally suffers the effects of John Wick’s wrath, earning a memorable conclusion to his character.

“John Wick” became a surprise hit that changed action movies for the better, earning $86 million at the box office off of a $20 million budget and spawning a massively successful franchise that includes three sequels and the spin-off film “Ballerina.” Altogether, the franchise has earned over $1 billion at the global box office — and Winters can lay claim to being there to help get the ball rolling.

Who could forget the character Keith “The Vulture” Pembroke on the long-running cop comedy series “Brooklyn Nine-Nine?” Yup, that was Dean Winters, bringing his tour-de-force, low-brow obnoxiousness to the playful precinct every time his abrasive self swooped in and scooped up a case. It happened exactly nine memorable times during the series’ acclaimed eight-season run.

Whenever Winters popped in to boss around Detective Jake Peralta (Andy Samberg) and Lieutenant Terry Jeffords (Terry Crews), Pembroke stole the show with his arrogant penchant for inserting himself into the middle of a flourishing investigation. He’d even go on to steal the credit for closing the case, hence earning himself the insulting scavenger nickname of The Vulture. And a promotion.

From lewdly planning to hit on his dead brother’s widow to flippantly referring to his fellow cops as turds and wieners, The Vulture rubbed everyone the wrong way — except for “Brooklyn Nine-Nine” viewers, who couldn’t get enough of the crass copper.

When the Denis Leary-starring series “Rescue Me” premiered in 2004, the New York City-based dramedy centered around firefighters quickly became a critical darling. It earned positive reviews and numerous award nominations for how it handled a post-9/11 New York setting, while blending it all with dark humor.

For seven seasons of the series, Dean Winters wove in and out of the storyline as the New York police detective Johnny Gavin, brother of Tommy Gavin (Leary), himself a member of the New York Fire Department. Even though the brothers’ lives are intertwined, they mainly have a contentious relationship. Especially after Johnny sleeps with Tommy’s estranged wife Janet (Andrea Roth), potentially fathering a child with her.

During Season 3, Johnny meets a surprising fate. He continues to haunt Tommy throughout the remainder of the seasons, regardless, leading Tommy through some dark times. The unexpected storyline twist led to a rumor that Winters and Leary had a rough relationship, although there was never any concrete evidence to back that story up. As Winters continued to make appearances all the way to the end of the series in 2011, things seemed just fine.

Dean Winters first flexed his comedic chops on the critically acclaimed comedy juggernaut “30 Rock,” as Liz Lemon’s (Tina Fey) totally awful-but-strikingly funny on-off boyfriend Dennis Duffy. He would show up to drop crass one-liners while proudly being a self-referential Irish-American stereotype. Winters’ powerhouse performance helped take him to new heights in his career.

From 2006-2012, Dennis Duffy inserted himself into Liz’s life, appearing in a total of 15 episodes. He often left everyone scratching their heads as to why a smart, thoughtful woman like Lemon would keep gravitating back to a low-brow dullard and borderline bigot like Duffy. The man’s nickname for her was “dummy,” and he smugly anointed himself as New York City’s “Beeper King,” even though the technology had clearly become obsolete. Still, he manages to live on as one of the most memorable “30 Rock” recurring guest stars to ever grace the satirical sitcom, leaving behind a lasting legacy of teaching viewers of a certain age about what a “rat king” is. He even reunited with co-star Fey, in 2019, for one of his famous Allstate Mayhem commercials.

Dean Winters’ time in the spotlight dates back to 1997, when he grabbed viewers’ attention by playing the compellingly manipulative Ryan O’Reily on the ground-breaking HBO show “Oz.” For six seasons, “Oz” helped shape modern television, opening the door for other game-changing series like “The Sopranos” and “Six Feet Under.” The compelling prison drama was a turning point for HBO, revitalizing the cable brand and stealing viewers from the standard primetime networks that had maintained a stronghold on the scripted television market for decades.

As O’Reily, Winters quickly became a fan favorite. He was both easy on the eyes and thrillingly cut-throat behind the guarded walls of the fictional Oswald State Penitentiary (also known as “Oz”), where he wheeled and dealed to come out on top at the ruthless prison. Viewers caught him committing casual horrors like sneaking ground up glass into another inmates food in order to kill him, and orchestrating the murder of the husband of a prison nurse that he had a crush on. All in all, it was a wild career start for a guy we know better today as the physical embodiment of mayhem.