"I'm glad that when I came out I didn't know beforehand or else I would've been way more nervous," he tells Spinner. "There's a rap part to my set and if I had known that Ad-Rock was going to be there I would've... I don't know what I would've done!"
Rest assured, the set went smoothly. But it certainly gave O'Regan a lot to think about.
"Sometimes it's not the best to hear that you're rapping in front of a member of the Beastie Boys and a member of Le Tigre and Bikini Kill," he says. "That was really crazy -- and stuff like that is way more important than getting a song on some television show. I can't think of anything more rewarding than that."
Well, how about a pop megastar using one of your songs as her pre-concert music?
"I went to Katy Perry this summer and the biggest head trip of all time was when we were waiting for her to come on and nine-year-olds were filing in, 'All Yr Songs' started playing in the pre-show," O'Regan says.
It wasn't just a "head trip" for him, though, hearing his song piping through the stadium prompted him to start critiquing his own sound. "Obviously, no one there heard the song but hearing something in that context, relative to everything else, it sounded so small and I want to do something bigger."
A bigger, poppier sound is something O'Regan is focusing on as he finishes up his follow-up to 2010's 'Special Affections.' Now working with producer Damian Taylor (Austra, Bjork, the Prodigy) in Montreal, the popsmith says his new record is "more fully-formed; it was what the last one wanted to be."
"I'm really excited about it," O'Regan says. "I'm trusting and hoping that it'll appeal to as many people as possible. I'm never trying to alienate anyone with my music -- it's not muzak!"
The "whole package" of the yet-to-be-titled record (which includes more fun music video treatments) is far from being completed, but, with any luck, new material will start to roll out soon.
"At the core, it's pretty much a continuation of a lot of the themes and styles explored in the last one," O'Regan reveals. "That last record was my bedroom record and I want to get outside of that with this record.
"I guess that one was more the sound of someone attempting to make pop with very limited means, with a very limited understanding into creating songs. And with this one, it's trying to create the archetype of what a popular song is."