With Dempsey Bolton’s upbeat anthems it’s hard to tell if it’s his heart that’s breaking or if he’s the heartbreaker. Introspective lyrics layered with punchy beats defines Dempsey’s self-produced indie pop hits. Coming off winning a YYC Music Award for Pop Single of the Year with his song “Couple Minutes” and having recently showcased at Breakout West and MUSEXPO LA, Dempsey is looking to continue this momentum into with the release of his sophomore album, “i’m not sad, u are” in April of 2025. The album is a self-produced tour-de-force, featuring anthemic choruses and dynamic arrangements, cathartically tackling themes of isolation and heartbreak.

Press

"From the hand of Dempsey Bolton we get funny indie for battered souls" – Mickey’s Weekly

"Canadian singer and songwriter Dempsey Bolton is currently one of the most exciting R&B / soul newcomers on the international music scene" - Music AllNew

“With a sense of melody above all, a production of beauty and a talent that transpires and leaves no chance for doubt, Dempsey Bolton plunges us into a musical world that will have an effect on you” – Iggy Magazine

“[Dempsey] offers wonderfully engaging R&B pop with beautiful melody and production” - POPMUZIK

Hype

Charting

NACC Top 200 Chart - i'm not sad, u are, 6 weeks, #111 peak

Spotify Editorials

New Music Friday Canada, Mood Ring, It’s a Bop

Apple Music Editorials

New In Pop, Breaking Pop, Pure Pop Radio, New Music Daily, Breaking Alternative, New in Alternative,

New In Indie

YouTube Features

dynmk (980k), Discovering Music Club (150k)

Sled Island