Gregory Pepper

Gregory Pepper is a Canadian songwriter, multi-instrumentalist and illustrator.

He began his artistic career selling nude Bart Simpson drawings to classmates, eventually ascending to the rank of high school ska savant in the early 2000’s.

As Gregory Pepper & His Problems, he released eight full length albums ranging from experimental bedroom twee (With Trumpets Flaring, My Bad, No Thanks), to brash power pop (CHORUS! CHORUS! CHORUS!, Black Metal Demo Tape), and baroque orchestral pop (I Know Now Why You Cry, Under a Heather Moon).

He released The Great Depression as Common Grackle in 2010, a collaborative hip-pop project with label-mate Factor Chandelier. The pair reunited in 2021 for the more introspective quarantine study Old Dog New Tricks Who This, as well as joint singles with indie rap luminaries Awol One, Kirby Dominant, Open Mike Eagle, and CESCHI.

His most ambitious musical feat, The Complete DAD YEAR Recordings (2017-2018), saw Gregory Pepper writing and recording a song every week for one entire year whilst navigating loss and newfound fatherhood. “It was the most rewarding thing I will never do again” he said of the resulting 50-track album in retrospect.

Post-Problems 2025 welcomes a new Common Grackle single (Dolores) as well as a forthcoming 10-track solo effort - tentatively titled No More Skulls - which treads the familiar path of hopeless optimism and quirky arrangements which Pepper continues to craft in spite of himself.