After bouncing around the country writing songs and honing his craft, singer/songwriter Cass McCombs’ insightful and emotionally rich work caught the ear of Baltimore label Monitor Records, who released his first EP, 2002’s Not the Way. McCombs’ first album, A, was released early the following year and was distributed in Europe and the U.K. by 4AD. Early in 2005, the “Sacred Heart” single revealed the more polished and poppy direction of his second album, PREfection, which arrived that spring. Recorded in studios and at home, McCombs’ third album, Dropping the Writ, was released in October 2007, followed by Catacombs in 2009. For 2011’s Wit’s End, McCombs opted for a dark, chamber music-inspired sound. Before the year was out, he returned with the “Bradley Manning” single, which he premiered on the Democracy Now News Hour, and another new album, Humor Risk. The following year, his song “Love Thine Enemy” was performed by the National and Bob Weir. McCombs released the sprawling 22-song double album Big Wheel and Others in 2013. The record, which featured vocals from actress Karen Black on one track and contributions from musicians Mike Gordon (Phish), Joe Russo (Furthur), and Joan Wasser (Joan as Police Woman), found the singer digging deep into Americana and exploring a wide range of sounds and styles.