His art practice spans a range of media including photography, painting, drawing and video.
[1] Dempsey later directed and co-wrote his second feature-length movie Deadman's Barstool (2018), and played lead actor in Flasher (in post-production) .
[2][3][4][5][6] In 2018, he was featured in New York Magazine's "The Cut - They Seem Cool" column entitled, "The Painter Who Loves To Hate The Art World.
He went on to do a residency at the Villa Waldberta in Feldafing, Germany in 2012, which resulted in the exhibition Next Generation: Contemporary American Photography at Munich's Pasinger Fabrik & Amerika Haus that same year.
His first two-artist exhibition in the New York City was held at the BOSI Contemporary gallery in 2012, curated by Renato Miracco and entitled Mutatio.