Dougie Poole's music has been described as an "intersection of experimental pop and outlaw country."[5] He released his debut EP Olneyville System Special in 2016.[6]
In 2017, Poole released his debut full-length album Wideass Highway.[7] In a review of the album, Cameron Perry wrote that Poole "twists classic country into something strange and authentic."[8]The Morning News included Wideass Highway in their list of The Top Albums of 2017.[9] Dougie Poole's 2017 song "Don't You Think I'm Funny Anymore" was included in The Fader's list of under-appreciated songs from 2017.[10] Dougie Poole has shared stages with Jerry Paper, Sean Nicholas Savage, Dark Tea, New Love Crowd, and Drugdealer amongst others.[11][12][13][14]
Poole's sophomore album The Freelancer's Blues was released in June 2020.[15]