Jake Brennan & The Confidence Men

A Boston native whose songs fuse equal measures of passion, heart, and swagger, Jake Brennan first attracted notice as the frontman of the punk outfit Cast Iron Hike. He entered the group in 1993 at nineteen and recorded both a full-length album and an EP before the inflexible stylistic limits of punk began to chafe; exposure to country, blues, and roots music—partly absorbed from his father, Dennis Brennan, a locally revered Boston musician—prompted the shift. Eventually Brennan struck out alone and assembled Jake Brennan & the Confidence Men, whose lineup included guitarist Eric Barlow, keyboardist Scott Janovitz, drummer Rob Dulaney, and bassist Binky.

The band began working the Boston club circuit and received an early boost in 2001 when they shared a stage with a reunited Treat Her Right, Paul Q. Kolderie filling in on bass for the late Mark Sandman. Impressed by what he heard, the veteran producer invited the group to his newly launched studio for a three-day recording session. Those dates yielded most of Brennan’s debut album, Love & Bombs, issued by Yep Roc in autumn 2004; a documentary chronicling the sessions, Singer-Songriot, appeared as a bonus DVD on the first pressing. That same year Jake Brennan & the Confidence Men also claimed victory in WBCN’s Rock Rumble, the station’s celebrated Boston “battle of the bands,” and subsequently supported tours by Tommy Stinson and Evan Dando.