Born and raised in rural Berlin, Massachusetts, he began playing Worcester-area and then Boston-area clubs after graduating from high school. For more than two decades, he worked with Boston bands like the Martells, who scored a number one hit on Boston rock radio in 1980; later in the decade, his band Push Push flirted with several major label recording deals. In 1990, a major label signed the Rhode Island act Young Neal and the Vipers, and label executives pressured them to drop their lead singer and bring in Brennan. That didn't last very long, and after other "almost record deals" fell through, Brennan took a break from his singing and songwriting to work as a warehouse foreman. After a few months, he found himself growing into an increasingly prolific songwriter; some of the results -- frequently about life's hardships, trials and tribulations -- were showcased on his 1995 debut album for Rounder, Jack in the Pulpit, on which he was accompanied by guitarist Duke Levine and drummer Billy Conway of Morphine. Iodine in the Wine followed in 1996, and in early 2000 Brennan returned with Rule No. 1. ~ Richard Skelly