[5][6] He self-released the four-track EP Waiting Ones in 2012, a collection of "low-fi blues-influenced folk-punk recordings and handclap percussion" that gained the attention of music blog Aquarium Drunkard.

[6] Booker's self-titled debut album was recorded in December 2013 at The Bomb Shelter, an analog studio in Nashville.

[26] The title track's references to police brutality and activism garnered Booker coverage in politically-leaning outlets including Mic, which noted the album's "urgent synthesis of blues, gospel and soul — forms with long histories of translating black pain into uplifting and enduring compositions ... with a raw and unforgiving candor that's reminiscent of downtown New York punk.

"[27] The opening track "Right on You" was shared on April 19 by The Fader which called it "a staticky, high-tempo ballad that packs a punch".

[29] Since the album's release on June 2, 2017, WNYC has described Booker as "a punk & grit-infused songwriter whose ecstatic and soulful sounds channel vintage soul-rock, gospel, and blues.

"[30] On June 19, "Witness" was shared by Pitchfork alongside a review saying Benjamin "makes retro music feel modern, reflecting on racism in America while drawing on blues, soul, and gospel.

Towards the end of 2024, Booker started teasing a new album called Lower after releasing a single called "LWA in the Trailer Park", along with a music video for the track on October 16, which gave a pre-save link for his album set to release on January 24, 2025.

On January 14, 2025, Booker released "Slow Dance in a Gay Bar" as the final teaser single, as well as a music video for the track uploaded the same date.