After bouncing around the country writing songs and honing his craft, McCombs' work caught the ear of Baltimore label Monitor Records, which released his first EP, 2002's Not the Way. His debut 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. Recorded in studios and at home, McCombs' third album and Domino label debut, Dropping the Writ, appeared in October 2007, followed by Catacombs in 2009. The latter album featured backing vocals by actress Karen Black and found McCombs co-producing with Ariel Rechtshaid. For 2011's Wit's End, McCombs opted for a dark, chamber music-inspired sound that landed him in the Top 15 of Billboard's Heatseekers and Americana/folk charts. It was also co-produced by Rechtshaid. Before the year was out, McCombs returned with the "Bradley Manning" single, which he premiered on the Democracy Now News Hour, and another new album, Humor Risk (produced by the songwriter, Rechtshaid, and John Webster Johns). 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 again featured vocals from Karen Black on one track and contributions from musicians Mike Gordon (Phish), Joe Russo (Furthur), and Joan Wasser (Joan as Police Woman), saw the singer digging deep into Americana and exploring a wide range of sounds and styles. Domino then released an anthology of McCombs rarities and B-sides called A Folk Set Apart in late 2015.
His eighth studio full-length, 2016's Mangy Love, took on sociopolitical topics with accompaniment that dipped into psychedelia, reggae, Baroque pop, and funk. His debut for Anti-/Epitaph, it featured over a dozen guests, including fellow indie songwriter Angel Olsen, guitarist Blake Mills, and Stuart Bogie (Hiss Golden Messenger, Antibalas). He followed that with Tip of the Sphere in 2019, resulting in his first Top Ten placement on the Billboard Heatseekers chart. With a backing band that included keyboardist Frank LoCrasto, bassist Dan Horne, drummer Otto Hauser, and several guests, it was engineered by Sam Owens (aka Sam Evian). The crew of McCombs' tenth long-player included the likes of Wynonna Judd, Cactus Moser, Danielle Haim, and Shahzad Ismaily, among others. A playful examination of both music and the human condition, Heartmind arrived on Anti- in mid-2022. ~ Tim Sendra & Marcy Donelson, Rovi