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John O'Regan, the artist latterly known as Diamond Rings, has just played his first New York show with his new band and a new album, Free Dimensional, on the way. He feels good. He says "I feel good" three times. Minutes later he tells me he's "pretty OCD," and of course: Pop music is built on repetitive fixation. So is a pop star's identity, which has to evolve recognizably, like a costumed superhero you can believe in even if he's not real. O'Regan, you should know, is pretending very seriously.

Gone is the rainbow makeup and mismatched gear and with it the half-kidding ambition that augured the 2010 Toronto fame of Diamond Rings. His bleached crop and glam-jock clothes remain, along with the arena-ready moves. Now, in white jeans, white kicks, white sunglasses and a white jacket splashed thick with rhinestones, O'Regan is Diamond Rings emerged from the rough.

The show was at Lower Manhattan's ninth circle of insufferability, Le Baron, and packed with private invitees; each got an access badge reading "The World of Diamond Rings." It's still a small world, and O'Regan, offstage, gravitates away from the centre. This event must be the work of his major, major new label, EMI. He nods. "But I approved it," he says.

"What EMI would call marketing," wrote Alex Molotkow in her August Toronto Life profile of O'Regan, "he would call art." The profile focussed on O'Regan as former indie band leader, now DIY pop star "going pro." Incidentally, it marked the point at which he became too famous and/or uncomfortable to read his own press, including the Toronto Life piece:

"Lisa [Howard, his cousin and creative boss] had to read it out loud to me, two weeks after it came out."

O'Regan wrote most of Free Dimensional last summer, with 2012 on his mind. "You're trying to give a large number of people that you've never met something that you imagine they're going to want," he says. Given the love-you-more swing of every new song, is that 'something' optimism? Really? "I think so," he says diffidently. "People know what's not right in the world. As much as I admire those artists who point out shortcomings of mainstream society, I think it's nice to have a boost, too."

If O'Regan has to choose between "mainstream society" with said shortcomings and the small, perfect world of people who recognize him as a genderqueer performance artist, I doubt he'll blink. "I didn't sign to the same label as Kylie Minogue because I wanted to make a chillwave record," he says. "You can't stay in that [independent] world forever. I've changed aesthetically and sonically, and I'm happy with it."

He's also changed his performance style. It's not just that the Diamond Rings sound is polished to a harder shine, with some songs – try the first single, I'm Just Me – sounding like genuine bubblegum, and one verse on which he raps exactly as well as Blondie. It's that where he once seemed a weird art school kid playing pop star, he now looks like a pop star performing weirdness. (Recently I spent 15 minutes in my friend's backyard talking to this super-chill, softspoken dude with a baseball hat and a beard, and not until he started talking about his new music, describing it as "Top 40 with a twist," did I clue that it was O'Regan in normie drag.)

That doesn't mean he has Katy Perryish ambitions. "In writing songs about friendship and love and empowerment, it was a challenge to not come off as self-aggrandizing or pretentious, or like I'm your camp counsellor," he says. He doesn't say Perry's name, or Lady Gaga's, but I see what he means. "I don't want to have a fan club that has its own hashtag. I'd rather have kids listen to me and feel like they can write their own songs than upload covers of mine to YouTube, any day."

O'Regan grew up in Oshawa, and he still seems to care more about teenage fans in the suburbs than the taste-making downtowners around him. The kids are why he makes pop, not visual art, although he studied the latter at the University of Guelph. He doesn't want anyone to have to go to school for four years to "get" him.

"Visual art constantly has to justify its own existence," he says. Adopting a swaggery, Vice-bro voice, he goes: "Is it art? Does it matter?" Then he shrugs. "Even the most banal, trite pop music exists unencumbered from discussions about relevancy. No one walks around with a Music Matters button. It just does."

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