In 2006, Chris started writing songs for a solo project, while playing intimate shows around Chicago, and posted four demo songs on his MySpace page. Adopting the name Sundowner, he finished recording his debut solo album with the help of The Lawrence Arms drummer Neil Hennessy on bass and Jenny Choi on cello, keys and backing vocals. The record, Four One Five Two (named after his parents' house, where he did much of his songwriting), was released on Red Scare records on March 13, 2007 and features reworked versions of the popular Lawrence Arms songs "100 Resolutions" and "Boatless Booze Cruise" (retitled "My Boatless Booze Cruise"); the latter was a song originally written and sung by Lawrence Arms band mate and bassist Brendan Kelly.
McCaughan went on tour as Sundowner with Mike Park in Feb-Mar 2008 in the UK and Europe on what was known as the "Beans On Toast" Tour, because that is all the pair could afford to eat. Asian Man Records released the second Sundowner album We Chase The Waves on August 10, 2010.