Brooklyn, NY-based Proud Simon has been, at times, a solo project; a small folk-rock band; a large ensemble with horns, woodwinds, and strings; and, in its most recent incarnation, a five-piece rock band. Mostly Proud Simon is really the songs and singing of Brian Keenan, plus whatever musical friends he can round up, and the sort of chamber pop Americana Keenan specializes in, along with his instinctive arranging skills, gives the band a unique, ornate, and atmospheric sound that still manages to sound somehow familiar. Proud Simon officially began in Rochester, NY, in 2003 when Keenan and friend Charlie Monteverde began jamming in a garage together, eventually recording and releasing an EP, Leaving, and a ten-song album, Sometimes a Stranger, in 2004. Expanding to a five-piece, the band released a second EP, Victory March Through the Brandenburg Gate, in 2005, after which that version of Proud Simon folded and Keenan moved to the Brooklyn area, rebuilding the band from the ground up and releasing the Bryce Hackford-produced Shoestring Universe in 2006, followed by Night of Criminals in 2008.