While that band was taking a break in late 2008, O’Regan 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 O’Regan 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 O’Regan more publicity. However, reactions on blogs alerted Sony to their error; the label formally apologized to O’Regan 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 Sebadoh’s “On Fire.” Around this time, O’Regan'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, June’s “Show Me Your Stuff” and September’s “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. ~ Heather Phares