The band was influenced by the thriving music scene of nearby Chapel Hill.
A debut LP, Piles of Dirty Winters was released on Arlington Virginia indie label Simple Machines in 1995, followed by a split 7-inch.
Reviews of The Raymond Brake's releases often noted that the band's sound blended strange tunings and timings with hooks and melody, observations which in turn led to comparisons bands such as Polvo and Grifters.
However, the same year saw The Raymond Brake's final release: the Never Work Ever CD EP on Hepcat Records.
Singer and guitarist Andy Cabic moved to San Francisco, and began performing with Devendra Banhart and Joanna Newsom.