Photography: David Waldman / Styling: Lisa Howard / Brick Wall pin by Alynne Lavigne

John O’Regan is the kind of musician who wears his influences on his sleeve. We’re not too far into our conversation at his technicolour Roncesvalles loft before O’Regan starts pulling out his favourite covers from a stack of thrift-shop LPs: Grace Jones’ Nightclubbing, Run-DMC’s Raising Hell, Janet Jackson’s Nasty, Queen’s The Game.

Having recently reinvented himself as the gender-bending glam-rocker Diamond Rings — a far cry from his day job as the bespectacled lead singer in post-punk quartet The D’Urbervilles (see our related story), where he performs in a toque and parka — John likes to talk about queer theorist Judith Butler and why one should match one’s eye shadow to one’s purple dunks. Leading a double life does have its unforeseen complications, of course. During a recent Quebec tour with Owen Pallett, on which he had landed the coveted opening slot, O’Regan had to borrow concealer from Pallett’s stepmom. Before O’Regan’s next gig in Montreal, he was sure to make time for a pit stop at a MAC store. “We had no time to sound-check,” O’Regan says, “but I was, like, ‘I need to get some glitter.’”

In Toronto’s bearded, skinny-jeaned indie scene, such anecdotes are rare, especially coming from the lead singer of a band commonly described as flapjack-eating hosers from Oshawa (“the city that MOTOvates Canada”). That contrast hasn’t hurt the rise of Diamond Rings; it may even have helped. The kitschy video for single “All Yr Songs” was a buzz track last fall thanks to glowing props from Pitchfork, and he has recently finished recording his debut LP, Special Affections. Opening slots for the likes of La Roux, Think About Life and Woodhands across North America can’t hurt either.



With O’Regan’s sonorous Ian Curtis–like vox promising sweet nothings over confectionary synthesizers and beats he composes in GarageBand and blasts during his shows from an iPod, the album is a host of bangers whose inspiration he attributes to Starz on 54’s discofied cover of Gordon Lightfoot’s “If You Could Read My Mind.” Like Lightfoot’s paperback novel, O’Regan’s songs deal in the sublime heartbreak of moving on: “Something Else” employs the lovelorn wail of an electric guitar as John describes an unrequited crush (“I know you know just what you like, and I am really not your thing”); “It’s Not My Party” revisits Lesley Gore with the punctuated piano coda of Alicia Keys’ “Fallin’,” musing, “we’re all grown up and that is good, we’re told, but when do grown-ups just become plain old?”

An austere pastiche of R&B slow jams, punky song structures and clever internal references, Special Affections is the perfect millennial soundtrack for sweet surrender — and O’Regan’s flamboyant, glam-rock image is icing for the music blogs and clothing designers currently courting his attention. Gentlemen Reg may be Toronto’s most visible queer balladeer, but he rarely wears zebra print leggings out in public.

Though he’s only 24, O’Regan has already graduated from art school at the University of Guelph (where he was on the volleyball team), toured the country in a post-punk band, fallen in love with ex–Barmitzvah Brother Sylvie Smith (with whom he started the side project Habitat in 2006 while Smith was his girlfriend), been diagnosed with Crohn’s disease and recuperated at home with his parents while checking in and out of hospitals for half a year — his rail-thin, six-foot-tall body is still recovering. If Special Affections reflects those experiences mostly through synth-rock ambivalence (the song titles include “Wait & See,” “Give It Up” and “Something Else”), it’s only because O’Regan is still figuring out what comes next. This is normal for people in their mid-twenties, even those who aren’t poised to become Canada’s next pop icon.

“This album has really been about getting to know myself a lot better,” O’Regan admits over brunch at Aunties & Uncles, “because I think what I am doing is, to a degree, sexualized, and really overtly so. I didn’t want to make a singer-songwriter record. I wanted it to be bold and daring.”

Going your own way can be lonely, however. When it’s just you onstage in a bedazzled jean jacket, without that feeling of strength in numbers, the pressure intensifies tenfold. Friends like Montreal illustrator Jack Dylan have reminded O’Regan that he’s taking every risk imaginable — writing his own songs, performing them to audiences solo, triple-layering his eye shadow. Though it was originally intended as an acoustic singer-songwriter project, O’Regan’s glamorous transformation has taken him and the people around him by surprise. But for the first time in his life, he says, he’s also feeling completely liberated. It’s as though his alter-ego has given him the courage to play himself in everyday life. And to wear nail polish.

His D’Urbervilles bandmate Tim Bruton has known O’Regan since they were seven, and admits he’s changed since his days as a high-school-jock triple-threat, mastering basketball, volleyball and lacrosse.

“He’s definitely matured into a different person than he was eight or 10 years ago,” Bruton says. “When I first went to Guelph, I remember that John hung out with all the hippies. He hitchhiked to BC one year and came home with this gross hippie beard. A friend of mine who’s known John for just as long as I have said, ‘John’s never changed, he’s just become more John.’

“I think people really love mystery, and it’s up to them to decide whether Diamond Rings is a character or not. I’m definitely not saying one way or the other.”

In one sense, O’Regan is hardly alone — it takes an entourage to create an icon. Like the artistic collective that surrounds the Haus of Gaga, the cultivated image of Diamond Rings involves many labours of love, not all of them O’Regan’s. His roommate, Colin Medley, directed the videos for “All Yr Songs,” “Wait & See” and the forthcoming “Something Else,” collaborating on the choreographed dance routines and glittery aesthetics that garnered 71,109 views on YouTube; O’Regan’s cousin, Lisa Howard, is his personal stylist; and his album boasts appearances from friends and gurus Gentlemen Reg and Katie Stelmanis.



And, despite the headaches of scheduling around his solo commitments, The D’Urbervilles will continue. Though fans may one day pressure O’Regan to choose between his personae — is he glam-rock or post-punk? Straight or gay? — the next development of John O. is his chief concern for now.

“The big thing that I’ve [become aware of], now that I’ve been reading a lot more queer theory, is the performance of gender,” O’Regan says. “And that, to me, is what this project is about, more than anything that’s necessarily related to sexuality. I still think it’s interesting — just based on whether I’m wearing blue jeans or black tights, glasses or eye shadow — that people’s wholesale perception of my identity changes. And, right now, it’s about trying to harness the power in that. If using the word ‘bisexual’ is what it takes to get people into the headspace to explain what I’m doing – then that’s fine. I just don’t want be boxed in, I don’t want people’s first perception of me to be a thought as to who I’m having sex with. Because the answer is… like… nobody.

“When you’re 24, people really want you to have your shit figured out… and, until I really committed myself to being a musician and an artist, I didn’t realize that [by doing it, I would be] giving up a lot of things. You’re kind of condemning yourself to be with your own thoughts a lot.

“It’s like you can touch everyone and no one, all at once.”