In his home in rural Texas, on the eve of his final tour in 2017, the singer-songwriter Daniel Johnston told me that he wanted to have a big song someday, what he called “a real hit.” That smash eluded him, but the cascade of poignant, often slyly funny songs he compulsively churned out over the past four decades garnered him a cult fan base that included Kurt Cobain, Beck, Jeff Tweedy and Lana Del Rey. His lyrics chronicled universal themes like loneliness, despair and unrequited love, but did so on almost uncomfortably personal terms. His struggles with mental illness were rarely far from the surface, and though he wrote about his world with childlike wonder, the emotions coursing through his music were often complex and heartbreaking. Here are 12 of his essential songs.