After one year of study in Chicago, he returned home to Boston to focus on music, recording his first album Sings "Walkin' and Talkin' for My Baby" and Other Smash Hits!

He recorded his first album of original material, Roll With You, in late 2007 with Q Division producer Ed Valauskas.

Speaking in March 2010 to British soul writer Pete Lewis, Reed stated the album was strongly influenced by the late 1960s/early 1970s Chicago soul music recordings of artists such as Tyrone Davis and Mel & Tim.

[3] Reed's song "Your Sins Will Find You Out" was featured in Episode 4[4] of the first season of Preacher, and "Recess" appears in both The Way Way Back (2013)[5] and Europa Report (2013).

[6] On January 22, 2019, Reed announced the April 12 release of his album, 99 Cent Dreams, via Yep Roc Records.