254 MINUTES WITH ...Dean Winters

His Allstate commercials pay his mortgage, and playing cops keeps him “from working behind a bar.”

- BY NATE JONES

THE HOUSE THAT MAYHEM BUILT is afifth-floor penthouse in Tribeca. Finding it was a labor of love for Dean Winters, who arrives on bicycle after getting his will notarized. The 61-year-old actor explains that there were three qualities he sought: outdoor space, a wood-burning fireplace, and an elevator that opened into the apartment. “I was being a real princess,” he says. He looked at 114 apartments over the course of four years before discovering this one. Today, it’s getting a proper face-lift. Winters introduces me to the contractors, Cesar and Oscar, working on his guest room. They are the first two of the roughly 25 people I will meet in the course of an afternoon hanging out with him.

In 30 years of acting onscreen, Winters has tended to personify a particular kind of outer-borough rage. Usually Irish or Italian, frequently a cop, spiritually a Jets fan. He often gets cast as the star’s boyfriend (or ex)—most famously on 30 Rock and Law & Order: SVU—or their brother, a part he played on both Rescue Me and Girls5eva. For the past 15 years, though, the bulk of his income has come from his side gig as Mayhem, the literal embodiment of chaos, in a popular series of ads for Allstate Insurance. His latest role, as an ornery detective antagonizing Denzel Washington's mogul in Spike Lee's Highest 2 Lowest, is basically the exact midpoint of all these characters: There's just something about Winters that makes directors want to put him behind the wheel of a speeding car and have him go nuts.