An album full of characters struggling against dead-end jobs, drug addiction and depression doesn't exactly sound inviting, but in the hands of John Darnielle, it's magic. Darnielle is a former psychiatric nurse; his catchy, gracefully appointed chamber-pop songs paint portraits of dread and paranoia with empathy and precision. "Harlem Roulette" – which jump-cuts from Frankie Lymon's final recording session, in 1968, to the 21st-century Pacific Northwest – is as close as a pop song gets to philosophy. The title track brings sumptuous horns and a glimpse of, yes, transcendence: "Clutch those broken headboards, ride the highest wave/Dusky diamonds shining in the far depths of the cave."

Listen to 'Transcendental Youth':

“I'm Yours”

Jason Mraz re-emerged after his disappointing second album with this lead single, a Jack Johnson-esque ditty about giving yourself fully to someone else. The success of the reggae-tinged song (it earned two Grammy nods and a spot on the Billboard singles chart for well over a year) was something the folk-pop singer never predicted when he wrote it in 15 minutes at home. "I played a happy-hippie chord progression that would probably work without 50 different Bob Marley songs," he told Rolling Stone. "I thought, 'It's too novelty. This is a nursery rhyme,'" concluding that "you can never guess what's gonna be a hit."