MEET MAYHEM: The Man Who Made Insurance Interesting

Dean Winters as Mayhem

When Allstate’s marketing chief, Mark LaNeve, resigned “for personal reasons” in February it left much of the ad industry wondering if the brand’s star spokesman, Mayhem, would be going with him.Since the Mayhem campaign was launched in June 2010, he has been an industry favourite and loved by consumers, who find the mischievous character hilarious.

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In the first year of the campaign, Allstate’s CEO, Thomas Wilson, thought that Mayhem was helping move business. “It’s working. If you look at our quotes and our new business, it’s way up,” he said on an earnings call in early 2011.

But at the time of LaNeve’s resignation, Allstate was losing market share and revenue from property-liability insurance premiums was flat in 2011, at $25.9 billion.

The campaign, which was edgy and entertaining for a financial services client, seemed to overshadow the very product it was trying to sell. 

But while Mayhem may not have brought the success that Allstate hoping for, Dean Winters has reaped the rewards of his dark comedic performance.

The actor, who declined to be interviewed, has been on a steady stream of TV shows since the late 1990s (including 30 Rock). But he often talks about the decision to play the destructive Mayhem as one of the best he has ever made.

Although he joked with Ad Age in 2011, “I wanted to become an actor so I didn’t have to put on a suit and sell insurance.”

Dean Gerard Winters was born July 20, 1964, in New York City.

He grew spent his early childhood in Long Island with his father, his former-model/dancer mother, two younger brothers, and his younger sister. Winters spent the majority of his formative years, however, in Arizona.

Winters is of Irish and Italian descent.

And he is fluent in Italian.

His brothers are also in the entertainment business.

Scott Winters is also an actor. Besides starring in several popular TV shows, he is best know as the guy who Matt Damon asked, 'How do ya like them apples?' in Good Will Hunting.

Brad Winters is a TV writer and producer.

Before Winters became an actor, he studied English at Colorado College.

In a 1999 article in The Arizona Republic, Winters said of his college experience:

'Mostly, I majored in trying to get the hell out of school,' he said. 'School and I never seemed to walk hand in hand.'

After graduating, he traveled the world before moving back to New York.

Winters hung out on the West Coast, Hong Kong, and Europe before meeting up in New York with his brother Scott, according to The Arizona Republic. By then, Scott had already settled on a career as an actor and convinced Dean to take an acting class with him.

He and his brother were bartending when they got their big break.

'The brother-bartenders were kind of like a gimmick around town,' said Winters. 'We had a pretty big following back in that day.'

The pair, however, had a habit of giving their following to many free drinks, which got them fired several times.

Fortunately, they managed to make a good impression on one of their regular customers, Tom Fontana. Fontana would go on to create the HBO series OZ.

Oz was a family production for the Winters.

Dean and Scott starred as brothers Ryan and Cyril O'Reilly on the critically acclaimed drama that follows the lives of inmates in a maximum security prison.

Brad Winters has writing credits on 6 episodes and miscellaneous crew credits on 16 episodes.

And their sister's husband, Jorge Zamacona, was a producer on 8 episodes of OZ.

After 6 years, OZ ended and he moved on to Rescue Me.

He played Dennis Leary's cop brother, Johnny Gavin, from 2004 until 2011.

And then landed the role of Dennis Duffy on 30 Rock.

You have probably seen Winters on a lot of other shows, where he tends to play bad boys.

He told one site:

'They're so much more fun. You're able to go to work and just kinda be an arsehole for twelve hours. Look, who doesn't wanna be an arsehole for eight hours a day?'

A few of his other credits include:

  • Casey Brinkley, the brother of Will Arnet's Chris Brinkley, on Up All Night
  • Detective Brian Cassidy on the first season of Law & Order: Special Victims Unit
  • John McFadden, Carrie's friend with benefits on Sex and the City
  • Charley Dixon on Terminator: The Sarah Connor Chronicles

In 2009, Winters died ... for 2.5 minutes.

After he recovered, he was offered the role of Mayhem.

Now Mayhem, has his own action figure.

You can buy the Mayhem action figure (or The Most Interesting Man in The World or The Old Spice Guy) for $79.99 on

And people dress up like his character for Halloween.

Since his debut in 2010, Mayhem (in his various costumes) has been a popular Halloween costume for men. You can often find a Mayhem paired up with his female rival, Progressive's Flo.

Mayhem has proved so popular that there is also a Spanish language version.

Since there is no direct translation of 'mayhem,' the Spanish-language character is called 'Mala Suerte,' or Bad Luck.

The role has been lucrative for Winters.

Although we cannot determine how much Winters makes for playing Mayhem, the New York Post reports that it is his highest-paying role to date. As of June 2011, he had already filmed a dozen commercials, recorded dozens of radio spots, and appeared in both print and online ads. That is a lot of residuals for the actor.

So if Stephanie Courtney makes about $500,000 a year playing Progressive's Flo, Winters could make at least that and possibly much more.

While he loves his three-piece Mayhem suit, he has another favourite fashion accessory.

While Winters doesn't like shopping, fashion is in his blood. His grandmother wrote for Vogue in the 1950s.

His signature piece is his boots:

'I've been wearing these Wesco boots my whole life. If I ever go onstage at the Oscars you can guarantee I'll be wearing my motorcycle boots.'

He thinks the Mayhem ads are really, really great.

He told the Chicago Tribune that if someone criticised his commercials it wouldn't bother him.

'I really don't care, because our commercials are better than 90 per cent of the movies that are out there, 95 per cent of TV.'

And he has no intention of stepping away from the role any time soon.

While Winters has experienced success on a number of hit TV shows, taking the role of Mayhem 'may be one of the smartest decisions I've ever made in my life. It's become an iconic campaign,' he told the Chicago Tribune.

But as iconic as it is, Mayhem has not succeeded where it counts. Allstate continues to lose market share. Let's hope Mayhem doesn't go the way of Priceline's Negotiator--off a cliff.

Mayhem might be dark, but The King is just plain creepy.

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