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Diamond Rings is the glammed-up solo project of Toronto musician John ORegan, who is also the singer/guitarist for indie rock band the DUrbervilles. While that band was taking a break in late 2008, ORegan started writing, recording, and performing as Diamond Rings. Instead of the post-punk of his group, he took inspiration from queer theory, androgynous trailblazers David Bowie and Grace Jones, and Stars on 54's cover of Gordon Lightfoot's If You Could Read My Mind. He also donned glitter, makeup, and spandex -- all of it a far cry from his years growing up as a jock. Diamond Rings made its debut in August 2009 with the limited-edition split single All Yr Songs, which ORegan released on his own Hype Lighter label; the video, which was directed by his roommate Colin Medley, received buzz from outlets like Pitchfork, CBC Radio, and Exclaim! A run-in with Sony Records, who had the video removed from YouTube because they thought it infringed on the copyright of their artist Chipmunk's song Diamond Rings, earned ORegan more publicity. However, reactions on blogs alerted Sony to their error; the label formally apologized to ORegan and Medley, and the clip was reinstated on YouTube. Diamond Rings returned with the Wait & See single -- which featured like-minded Toronto fixture Gentleman Reg -- in March 2010, released by Tomlab and featuring a radically reworked version of Sebadohs On Fire. Around this time, ORegan's profile was also rising, thanks to gigs with Owen Pallett, La Roux, Think About Life, and Woodhands, and dates at South by Southwest. Two more singles, Junes Show Me Your Stuff and Septembers Something Else, preceded Diamond Rings' first full-length, Special Affections, which arrived in October via Secret City. The album was issued in the U.S. a year later on Astralwerks, right as O'Regan was finishing up a tour opening for Robyn.
John O'Regan (born July 6, 1985) is a Canadian artist and musician best known by his stage name Diamond Rings.
Music career 
Early years (2003–2008) 
O'Regan got his start in music as one of the founding members of post-punk quartet The D'Urbervilles (later named Matters), where he was known as John O alongside Tim Bruton, Kyle Donnelly and Greg Santilly. He also formed the Casio-pop duo Habitat in 2006 with his partner at the time, Sylvie Smith of The Barmitzvah Brothers.
O'Regan began writing Diamond Rings songs in the summer of 2008 after graduating with a degree in Studio Arts from the University of Guelph. The inception of the new moniker and his earliest songs were written during a lengthy hospital stay while being diagnosed and treated for Crohn's disease.
According to O'Regan, the roots of Diamond Rings came from wanting to challenge people's expectations for a male pop star: “I wanted to do something that would unsettle not only me, but the audience too... I spent my whole life up to that point as an artist playing relatively nondescript indie rock. But I felt there was a part of me that really needed to get out. I wanted to express myself in ways that were beyond just musical—something that was dramatic and flamboyant and beyond myself in a way. And that became Diamond Rings.”
Singles (2009–2010) 
His first release was a limited edition split 7" vinyl single titled "All Yr Songs" that was distributed through his own boutique label Hype Lighter in August 2009. His friends PS I Love You were featured on the opposite side of the single. A music video for "All Yr Songs" was featured by CBC Radio 3, Exclaim!, and Pitchfork Media. The music video attracted controversy in December 2009 when it was removed from YouTube at the behest of Sony/BMG on grounds of copyright infringement. Apparently this was due to confusion between O'Regan's stage name and the song "Diamond Rings" by UK based rapper and Sony UK artist Chipmunk. When word of the slip up caught on throughout the blogosphere Sony/BMG withdrew its claim and issued O'Regan and video director Colin Medley a formal apology.
In March 2010, Diamond Rings released a new 7" single with German label Tomlab entitled "Wait & See", which features backing vocals from Toronto musician Gentleman Reg. The B-side features a cover of Sebadoh's "On Fire". The video for "Wait & See" was premiered on Pitchfork Media in February 2010. His next single was a 12" Chicago House inspired dance track titled "Show Me Your Stuff", which was released in June 2010 on Fucked Up guitarist Mike Haliechuk's One Big Silence imprint. The corresponding video also featured a cameo from Fucked Up vocalist Damian Abraham and has drawn comparisons to disparate artists such as Klaus Nomi, Nirvana, and Britney Spears
Special Affections (2010-2011) 
His debut full length album, Special Affections, was released in North America on October 25, 2010, by Montreal's Secret City Records. Thus far it has attracted positive reviews from Pitchfork, Exclaim!, and AllMusic. Lead single "Something Else" was released a month prior and features a cover of the Milla Jovovich song "The Gentleman Who Fell," with string arrangements by Canadian musician and Polaris Prize winner Owen Pallett. Following the album release Diamond Rings opened for Swedish pop star Robyn for the duration of her North American Body Talk tour in the winter of 2011. He also toured with PS I Love You in support of "Leftovers," a single that was cowritten by both O'Regan and the band and released on Toronto-based Paper Bag Records.
In May 2011, Diamond Rings began a six-week remix series titled "Remix Rainbow," which was conceived as a thank-you to a select group of musicians whose recent work gave Diamond Rings a sense of new-found inspiration. Among those featured in the series were Theophilus London, Junior Boys, and Handsome Furs. The artwork for each remix represents a different color of the Diamond Rings rainbow.
Diamond Rings has since signed with New York City-based Astralwerks Records, a division of Virgin/EMI Records, which rereleased Special Affections on June 21, 2011.
Free Dimensional (2012) 
In May 2012, Diamond Rings was featured on the Kids On TV song "Bobby", which appears on their album "Pantheon".
Diamond Rings released his sophomore album, Free Dimensional, on October 23, 2012. He and his band appeared on the Late Show with David Letterman on October 27, 2012 to perform its first single "I'm Just Me"; they also performed the song on The Tonight Show on November 7, 2012.
The second single "Put Me On" was listed as the Free Single Of The Week on iTunes Canada during the third week of November 2012.
In support of the album, Diamond Rings toured North America with a full live band. He began as the opening act for Stars on their fall tour starting in Portland, ME on September 20, 2012; his own cross-Canada tour, accompanied by Gold & Youth, concluded in Quebec City, QC on December 8, 2012.
Diamond Rings performed as opening act for Orchestral Manoeuvres in the Dark in North America in April and July 2013. The tour stopped in a number of U.S. cities, plus a gig in Vancouver and two shows in Toronto. He performed a number of additional solo dates during this time as well.
Personal life 
O'Regan is frequently questioned about his flamboyant persona and subjected to numerous insinuations about his personal life: "[A]s my profile grows and as more people hear my music and see my videos, it’s something that I realize: people want to know more. And I guess it’s up to me to really decide how much more I want to give.”
He has stated that he would prefer to let his work speak for itself: “I think right now for what I’m doing, I want my music and I want my lyrics and I want the songs and what I do on stage and in my videos hopefully to speak for [themselves]... I think some of the magic and mystery in music has been lost in contemporary culture. I think we as people have lost a bit of that sense of mystery or that sense of wonderment about the world and about each other. If anything, I hope what I do can help preserve some of that.”