"Yeah, it's kind of funny," he says. "We met at a birthday party back in 2002. Literally the minute I met her a bachelor friend turned to me and said, 'Dude, you're fucking done.' I remember one of our first conversations was about food. She asked—maybe she was testing me—but she asked if I liked to cook. I said, 'Yeah, last night I got some tilapia, deglazed it with cilantro and Negra Modelo beer.' She probably thought I was gay, but that wasn't the case, obviously."

At the time, Ray was on the cusp of morph-ing into the anti-Martha Stewart conqueress she is today. "She just had a show on the Food Network, which I'd never seen," says Cusimano, who was then providing legal counsel to a struggling independent-film company and playing on and off in the Cringe. But soon her show took off, the book deals started coming (they haven't stopped), Oprah called (Ray's frequent appearances on the show led to a partnership with Winfrey and King World Productions for her own syndicated talk show), and Cusimano found himself as entwined with Rachael Ray the brand as he was with the human; they got married in Italy in September 2005. Somewhere in there, Cusimano had an epiphany: "I was like, 'Do I want to lose money in independent film or make money in the Rachael Ray business?'"

Today, Cusimano plays a somewhat nebulous role in the Rachael Ray franchise. Unlike Martha and Oprah, Ray has yet to consolidate her businesses into one company; she is contracted talent—with CBS and the Food Network for the television shows, with Reader's Digest for the magazine, with knife and cookware manufacturers for the products. Cusimano, who works from home, doesn't collect a salary; he is co-owner of their nascent production company, Watch Entertainment, which he hopes to build into something like Oprah's Harpo Productions, though at the moment they have only one full-time employee.

One of the things he likes about the work is that it gives him ample time with his band. Since 2004, the Cringe have released two albums, neither of which sold particularly well, despite an appearance on Ray's talk show. ("Different demographics, I think," Cusimano says.) The group's latest effort, Tipping Point, has received from online music magazines reviews ranging from the vicious ("Oh, baby, this is one hot smoking turd of an album") to the slightly more kind ("Everything on this album you've heard before from someone else—and most likely you've heard it done better"). But like the gossip, this does not have any discernible effect on Cusimano's demeanor. He's an optimist. A guy having a good time. But don't get him wrong: He takes his day job seriously.

"Oh, I'm intimately involved with every aspect of the company," he says one day, standing inside a massive white-walled loft where his wife is being photographed for the packaging and ad campaign for a new Rachael Ray product. "It sounds clichéd, but every day is kind of different. I mean, maybe I'm at a photo shoot like this, making sure everything goes smoothly. Or maybe I'm looking over contracts. Or merchandising deals. I'm really the one who does all of that. I work real hard. If people want to be in the Rachael Ray business, they have to talk to me—"