Arts & Entertainment
4 min

Why you will love Diamond Rings

(if you don't already)

Diamond Rings Credit: David Hawe

In the indie clubs of Toronto, the idea of the pop persona was pretty much taboo until 25-year-old John O’Regan donned rainbow eye shadow and rechristened himself Diamond Rings.

Last year, the boyish-looking Oshawa native landed on the radar of the international music press when Pitchfork bestowed its “Best New Music” distinction on his single “All Yr Songs,” calling it an irresistible example of straightforward pop songwriting. Taste-making music pubs Stereogum and NME have covered subsequent singles and music videos for “Wait & See” and “Show Me Your Stuff,” and all that attention has helped Diamond Rings land gigs in the UK and Europe.

At the end of October, he’ll release his debut LP, Special Affections, via Montreal-based indie label Secret City Records. Its 10 tracks run a gamut of moods, from clubby to introspective, but are united by a reliance on choruses and hooks that aim big.

O’Regan wrote and recorded the entire album in his bedroom studio, with some engineering help from Ohbijou drummer James Bunton.

“He didn’t want it to sound like he was trying to do anything other than he was capable of,” Bunton says of Special Affections’ DIY sound. “I don’t think he wants to stay in the garage band realm forever. When opportunities and resources come his way to take it to the next level, he’ll go there and it’ll sound different.”

So despite the hype, Diamond Rings remains very much a one-man bedroom project. At 10:30am on the day of our interview, O’Regan answers the door to his apartment dressed in Chicago Bulls basketball shorts and a colourful poncho. He is slightly bleary-eyed, but his demeanour is bright. Inside, the scene is one of domestic harmony.

His roommates and long-time friends, brothers Colin and Adam Medley, are fully dressed and have started their days. Colin is eating breakfast as coffee brews, and Adam is glued to a computer screen in his bedroom. The spacious apartment is perfect for throwing house parties. Earlier in the summer, riot grrrl Emma McKenna held an album launch in their pad; she performed in front of a colourful mural of a blossoming tree that artist Sojo Truth painted on the wall.

Next to the mural, a life-sized cardboard cutout of Michael Jordan silently guards boxes full of seven-inch records for Tasseomancy, a freak-folky twin sister duo whose single O’Regan will launch on his Hype Lighter imprint at a party later that night. A mix of sports books, vintage music mags and recent Archie comics are laid out on the coffee table.

As a six-foot-five teenager growing up in Oshawa, O’Regan was destined to play basketball.

“I wanted to quit one year, so I didn’t go to the tryouts,” he explains. “But when they posted the list for the team I was still on it.”

Though his burgeoning music career has relegated basketball to the sidelines, O’Regan keeps his inner jock active by incorporating athletic imagery into Diamond Rings’ glammed-up pop persona. He’ll often mix and match high-tops and jerseys with tights and Technicolour eye makeup for his stage costumes, and he recently set a music video in a high school gymnasium (and locker room).

The style is a reflection of the fact that people have a multiplicity of influences and interests. Just because he identifies as queer and wears eye makeup doesn’t mean he can’t also wear plaid shirts, listen to prog rock or enjoy sports — or any number of other things.

He says his transformation has been received with some cynicism by his plaid-clad peers. During the interview he states repeatedly that his over-the-top pop persona comes from a desire to make an honest connection with his audience.

“For this tour I’m making an effort to keep it just to myself,” he says. “It’s a DIY sound and that’s how the album was put together and that’s still how I work. I think there’s something honest and real about that, and I haven’t totally maxed out with what I’m doing right now. There’s still stuff that I want to try.”

Prior to The Emancipation of Diamond Rings, O’Regan was best known as a guitarist for The D’Urbervilles, a band he formed with friends while studying art at the University of Guelph. He’s a regular in Toronto’s west-end indie-rock club scene and cites like-minded electrodance acts such as Kids on TV and Peaches as major influences.

When asked about his future goals, he responds cautiously.

“It should never be the kind of thing where sales or the number of people you’re pulling in to the bar becomes the goal. That’s when the music and the art start to suffer,” he says. “At the same time, you want to strive to grow and develop. I don’t want it to be, five years from now or even two years from now, just me up on-stage by myself.”

O’Regan uses a lot of metaphors to describe his ambitions. When explaining why he released Special Affections via a small label rather than a larger one — indie or otherwise — he likens most music execs’ plan for his growth to throwing up a cheap condo overnight.

“Let’s start with a bungalow and we’ll maybe add a garage with a bedroom over it in a few years if it makes sense,” he says. “It can work really well, but for every Lady Gaga there’s a number of people who don’t make it.”

He explains his desire to seem larger than life but still approachable by musing on the metaphysical appeal of Kylie Minogue. The veteran pop star released her 11th album, Aphrodite, this summer and he loves it. Moreover, he admires the way she manages to appear gracious while projecting an air of untouchable glamour.

“She’s almost like an essence more than anything physical or real or tangible — more than anyone I can think of right now in the capital P pop landscape,” he says. “She just seems to exist and sprinkles this magic around the song. There are songs that are great, and I’m sure any number of people could sing them just as well or similarly, but there’s something different about the fact that it’s her that completely changes the context of everything.

“I’m really fascinated with this idea of embodying this presence or being that’s greater than the bounds of your own physicality,” he adds. “You know she’s tiny, but it doesn’t feel that way.”

Diamond Rings’ Special Affections drops on Oct 25. Catch him on tour across Canada this fall. Check out for details:

Oct 26: Toronto
Oct 27: London
Oct 28: Hamilton
Oct 29: Ottawa
Oct 30: Kingston
Oct 31: Montreal
Nov 1: Guelph
Nov 18: Edmonton
Nov 19: Calgary

Watch Diamond Rings – “Something Else”: