10/11/2011 11:38 am ET Updated Dec 06, 2017

A-Sides with Jon Chattman: Diamond Rings Gives It Up

Diamonds are forever, and Canadian musician Diamond Rings is hoping his career lasts, well, for a very long time. Apologies for the crappy introductory sentence, but it makes sense when you chat with the artist who could be pegged as a cross between David Bowie and Lady Gaga. A few hours before his final tour date (a sold-out show Oct. 7 at Webster Hall in New York City), the man born John O'Regan discussed his career game plan and performed an intimate piano-acoustic version of "Give It Up" off his debut album "Special Affections" within a practice studio in the Music Conservatory of Westchester in White Plains, NY.

Diamond Rings' plan is essentially to keep making music and to not stop doing so until he's -- at the very least -- in his 40s. In other words, to rest is to die in this industry so don't expect the lipstick-wearing Canuck to take a long break between his well-received debut and its follow-up. Watch and listen below... preferably in that order.

"Give It Up" Live and Not Giving Up

About "A-Sides with Jon Chattman"

Jon Chattman's music series features artists (established or not) from all genres performing a track, and discussing what it means to them. This informal series focuses on the artist making art in a low-threatening, extremely informal (sometime humorous) way. No bells, no whistles -- just the music performed in a random, low-key setting followed by an unrehearsed chat. In an industry where everything often gets overblown and over manufactured, I'm hoping this is refreshing.