4. This Night (2002)

The sprawling, nearly 70-minute This Night was an audacious gesture from an artist who had only recently established his bona fides as one of independent music’s most talented exemplars. With its extensive running time and evidently intentional disjointed group of characters, This Night is a knotty, challenging affair somewhat akin to periodically difficult but hugely rewarding double albums like the Beatles’ White Album or Dylan’s Blonde On Blonde. Stylistic shifts abound, and the band often plays with first-take looseness, but all of it rings true, from the rollicking anthem to artistic ambivalence “Modern Painters” to the desperate confessional “Self Portrait With Thing (Tonight Is Not Your Night).” An adventurous album that sets the stage for later, no-holds-barred forays into experimentation such as the Archer On The Beach EP.