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Gregory Pepper and His Problems is a moniker used by the 26-year-old musician and visual artist who still treads shallow water in his hometown of Guelph, Ontario. Focusing primarily on melody and harmony, Pepper has amassed a repertoire of five hundred or so anthems of confusion and ambivalence, ranging from punkish-indie-rock to polished-baroque-pop. Always present ,though, is the disembodied voice of a scared child lost in the supermarket, crying out for his mother and angrily kicking his legs as she finally arrives to take him home. Pepper has toured alongside Islands, Born Ruffians, and The Smoking Popes, and has collaborated on albums with Noah23, Awol One of The Shape Shifters, and slew of underground hip-hop artists. He is currently supporting himself as a freelance illustrator while completing an album with Factor (Myka 9, Kirby Dominant) and preparing for a tour with his recently formed four-piece rock band.

Armed with a handful of cheap musical instruments, pens and alcohol as well as a mobile recording studio, Gregory Pepper has managed to record an album’s worth of material for every year of his lonesome existence. One of his most recent endeavors, “With Trumpets Flaring”, dares to be of Pepper’s most ambitiously despondent examinations of hopeless optimism. Drawing upon the poppy 1960’s melancholy of Brian Wilson and Roy Orbison as much as he does from modern trends in electronic and hip-hop, Gregory Pepper creates an experimental musical landscape that is instantly engrossing yet still rewards the listener through multiple replays.