38. Into It. Over It., 'Intersections' (2013)
Early into his run as Into It. Over It., Chicago troubadour Evan Thomas Weiss was known mostly for the sheer volume of his work. His most ambitious project, 2009's two-disc compilation 52 Weeks, found Weiss writing and recording one song per week for a year. But those salad days also allowed Weiss to woodshed, and by the time he got to Intersections, he sounds controlled, comfortable and confident in his own skin. "I don't think I've ever had so much fun making such a sad record," he says in Intersections' accompanying Web documentary, and for sure, the album finds magic in contradictions. Weiss' amicable, off-the-cuff delivery is the sugar that makes Intersections' heartbreaking lyrics go down, while his crystalline guitar figures dart and dance around the misery. A.B.