Dougie Poole's music has been described as an "intersection of experimental pop and outlaw country." He released his debut EP
Olneyville System Special in 2016. In 2017, Poole released his debut full-length album
Wideass Highway. In a review of the album, Cameron Perry wrote that Poole "twists classic country into something strange and authentic."
The Morning News included
Wideass Highway in their list of The Top Albums of 2017. 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. Dougie Poole has shared stages with
Jerry Paper,
Sean Nicholas Savage,
Dark Tea,
New Love Crowd, and Drugdealer amongst others. Poole's sophomore album ''The Freelancer's Blues
was released in June 2020. His third album The Rainbow Wheel of Death
was released in February 2023. A live album, At Tubby's'', was released in July 2025. == Discography ==