5. Jonathan Richman, "That Summer Feeling" (1983)

(listen)

I like how Jonathan Richman comes at us like a kind of wide-eyed innocent, an outright naif even, charming and boyish and silly. But let him close and the game becomes more evident. Perhaps nowhere more so than in "That Summer Feeling," from the 1983 album Jonathan Sings! The whole album is worth tracking down. The song that opens it is a kind of nursery inversion of Alice Cooper's "School's Out," seemingly all about the free and easy pleasures of the warm season, with a lot of free and easy sing-songy rhymes to move it along: "When the cool of the pond makes you drop down on it / When the smell of the lawn makes you flop down on it / When the teenage car gets the cop down on it." But this is no nostalgia trip. This is about the kinds of things you live with all your life, propelled against your will through time, the pain and regrets and longing that inevitably accrue. He's serious and he makes it plain as sunshine: "But if you wait until you're older / A sad resentment will smolder one day / And then this summer feeling will come haunt you / Then that summer feeling will come taunt you / That summer feeling will hurt you / Later in your life." Who is Jonathan Richman and what does he want? What is he telling us? I'm still not entirely sure, and I'm not convinced he could even articulate it himself. But he's working on the deep levels when he's at his best, and just like that summer feeling, if you listen close enough, he's going to haunt you the rest of your life.