Born and raised in Hamilton, Ontario, Caplan moved to Halifax for college but stayed when he discovered the city’s rich and interwoven music scene. With his band The Casual Smokers, Caplan released two acclaimed albums, In the Time of the Great Remembering (2011) and Birds with Broken Wings (2015). The sound is rooted in Caplan’s resonant baritone voice, at times sounding like lamb’s wool, and in another moment like steel wool, supported by a wide-ranging tapestry of piano, accordion, organ, clarinet, saxophone, violin, drums, and the occasional acoustic guitar.