FINALLY! Relocated this obscure jam that I've had randomly pop back up in my head and stuck there for weeks now. Came out like 7 years ago and I couldn't freaking remember who sang it or the name of the song. Was listening to random indie sampler albums I had and bingo! Band is Blue Hawaii from Montreal. Total earworm of a song:
https://www.youtube.com/watch?v=iLVAxEYB0-Y