What ever happened to Diamond Rings?

"How did you find my new email?" 

When I first reached out to John O'Regan to see if he would be interested in talking about his musical career as Diamond Rings, he seemed surprised that someone in the music industry had actually found him. He had made "a bit of a French exit" when he decided to walk away from music shortly after his 2012 sophomore album, Free Dimensional. Since then, with the exception of a few cover songs that surfaced in 2017 under the moniker JG Ballad, O'Regan has stayed completely silent.

"If you say no for a while, eventually people just stop asking," he says of interview requests over the years. "But, yeah, it felt like maybe time to say yes for once."

It's a question that comes up occasionally in Canadian music circles: where did Diamond Rings go? Regarded as one of Toronto's most exciting acts of the early 2010s, O'Regan's solo project (he was previously the singer of the local rock band the D'Urbervilles) appeared to be a hit. He had garnered the attention of taste-making sites like Pitchfork, Stereogum and Spin Magazine; he signed to Astralwerks in the U.S. (now home to electronic heavyweights Marshmello and Alison Wonderland); he even opened for Robyn. 

But at the tail end of his Free Dimensional tour in 2012, he was dropped by Astralwerks. "The record wasn't selling, not that anyone's records were selling," he reflects. Even though being dropped was crushing news, O'Regan felt some relief, suddenly realizing that this was an opportunity and a possible way out. "I didn't really know what I wanted more: for them to tell me I could make another album or to let me go." 

Diamond Rings' last show was in Toronto at the end of 2013. He didn't have a proper plan for what to do next and he felt it would've been too silly to post any official announcement. That type of grandeur is reserved for larger acts or bands, he thought. Instead, he informed his band, packed his bags and bought a one-way ticket to Warsaw, Poland, with his partner, Zosia Mackenzie. 

Fast forward to 2020: on a sunny mid-September weekend, O'Regan is calling from a hotel room in North Bay, Ont., where he is working as the art director on Phillip Noyce's new film Lakewood starring Australian actress Naomi Watts. Wearing a black sweatshirt, black glasses and his hair — now a chestnut brown compared to his days as a platinum blond pop star — swept back, O'Regan could easily blend into any crowd if it weren't for his signature towering height. The reality is that O'Regan hasn't really gone anywhere. Other than "not getting out much," the man behind Diamond Rings has shifted careers. Instead of being in front of the camera, he now works behind it. "I get to go and be a part of something that's bigger than me," he says. "It's been really refreshing just being able to tell someone else's story."

O'Regan says he accidentally fell into the film world, mostly thanks to Mackenzie, who is a fellow art director. When the two first started dating (they met at a Diamond Rings video shoot), she introduced him to the films of Errol Morris and other celebrated filmmakers, which made O'Regan realize "there was more to film than what I've been exposed to, which was a sort of hodgepodge of good and bad films. It was a really big awakening for me." 

Thanks to Mackenzie and some other connections he had in the film industry, O'Regan found his way onto the sets of some independent Canadian productions such as Matt Johnson's Operation Avalanche and Nathan Morlando's Mean Dreams. O'Regan is credited on those films as a set decorator, but has since moved into overseeing set designs as an art director for films like 2018's Giant Little Ones and last year's Castle in the Ground.

"If you want to dissolve your ego quickly, there's nothing like packing a cube truck for 12 hours a day, five days a week for five weeks," O'Regan says. "It's like a tour where you just don't go anywhere." 

The 'surreal' beginnings of Diamond Rings 

O'Regan hasn't thought much about Diamond Rings in the intervening years. When I informed him of this year's 10th anniversary of his debut album, Special Affections, he confesses that he hadn't listened to it in a long time. But he still looks back at that time fondly, perhaps even more grateful now than before. "That was a really special time," he recalls, "That process, from the first video on, was really pretty sudden and pretty surreal."

Diamond Rings came to life in 2008, after O'Regan was hospitalized with Crohn's disease. Having "touched my own mortality," as he describes it, O'Regan was forced to take a step back and recalibrate everything in his life, including his music career. "I knew I wanted to do something that was going to scare me a little," he says. Part of his inspiration came from a painful past of getting bullied, where kids at school would tease O'Regan by calling him gay. "I was on the receiving end of a lot of crap," he recalls. "I guess, with Diamond Rings, I embraced those sorts of insults in a way that, aesthetically, kind of embodied those stereotypes that people were throwing at me."  

What came out of that was a new persona, a colourful, androgynous look that was inspired by chameleons like David Bowie, and a sound that combined lo-fi garage rock with earworm pop melodies. Sporting tights, a pink tank top underneath a denim jacket and a face adorned with rainbow makeup, O'Regan's debut single and music video for "All Yr Songs" epitomized a DIY spirit that powered much of Toronto's indie-rock music scene at the time. Just based off that single alone, Diamond Rings unexpectedly got the attention of music fans outside of the city. "It's fun to hear a gulping James Murphy-esque voice doing those Amanda Palmer/Regina Spektor hiccups," Pitchfork wrote in its best new track writeup of "All Yr Songs." 

By the time he released Special Affections on Oct. 25, 2010, there was a palpable buzz surrounding Diamond Rings. But critics across the board accepted his brand of "laptop rock," as the A.V. Club called it. "O'Regan gives his transformation a thrilling edge," Spin Magazine praised. Pitchfork gave the album a flattering 8.2 score. O'Regan himself is little harder on himself in retrospect: 

"In terms of the sound of music now, the songs aren't really anything that I think stand out, but I'd like to imagine that that was still an era where the idea of just seeing one person onstage with a backing track was not as normal."

'Poster boy for queer art rock' 

Another part of Diamond Rings' success that O'Regan hadn't prepared for was the immediate interest in his personal life. Due to his androgynous presentation, and some close reading into his music — for example, he sings about "living double lives" on Special Affections opener "Play By Heart" — he was quickly branded as "a poster boy for queer art rock," as Xtra wrote.  

I just don't think I was prepared for the degree in which that conversation shifted.- John O'Regan

But in interviews, O'Regan shied away from topics of sexuality and never defined himself. Part of that is because he saw Diamond Rings as an asexual figure, but the other part was because he was admittedly in the middle of a journey of self-discovery. 

"I would say a lot of what I do and feel in life, for many people, would qualify under the banner of queerness," he says now. "But I was figuring out my shit and I was doing it in public. I do think a lot of folks didn't want queer to be the answer; they wanted either gay or straight. It was sort of a didactic and binary time. And fans and journalists wanted to reduce that to some sort of salacious quote or soundbite. I just don't think I was prepared for the degree in which that conversation shifted." 

In many ways, the whirlwind nature of O'Regan's rise added to the anxiety he had around these discussions. Often, he would get swept into a room, be told to perform a handful of songs, and given five minutes to answer rapid-fire questions. "There's a lot of nuance that gets lost," he explains, now over an hour into our conversation. (During our call, he often looks to his right, staring outside his window, taking long pauses to carefully select his words.) He commends artists today who are able to be more open about topics like gender and sexual fluidity, but in his experience, asserts that "these types of conversations didn't exist then." He adds, "Whether I would describe myself as queer now … fortunately, as an art director, it's not really something that anyone ever asks."

A return to music? 

By the time he found out he had been dropped by his label, O'Regan felt stuck in a number of ways. In addition to the pressures of answering personal questions, musically, he believed that he had "stalled out in this kind of weird middle ground," unable to imagine a bigger (or smaller) potential for his sound. On Free Dimensional, O'Regan dialled up the synths and club beats, polishing any lo-fi edges he had into a more pristine pop package. But without a major label backing him, his sound had reached its ceiling. 

The internet was also evolving during that time, which presented a problem to the shy, soft-spoken artist. "The part that I really grew to despise was anything pertaining to social media," he says. "I think it really started to affect me negatively to the point where I just didn't want to do it. I didn't want to engage with it and it started feeling really vacuous and kind of gross." O'Regan, whose online presence is pretty bare nowadays, doesn't shame anyone who uses these platforms, but given the compromised state of social media now, he's glad that he stepped away from that aspect both personally and professionally. 

While O'Regan loves what he does now, he hasn't completely shut out the idea of returning to music. Even now, he says he has hard drives full of music that he'll sometimes pull out and play for friends, but there's still a strong sense of hesitation and anxiety around putting himself out there again. (Privately, he has been working with Mackenzie on a new album she's spearheading called Szaio; a proper release has now been pushed back to 2021 due to COVID-19.) 

"I would say I have had far more success than I ought to have," O'Regan jokes. The key moving forward, he says, is "just waiting for a moment where, if and when I want to do something, it can be on my own terms."