In the late 1940s, a young woman moved to New York City and quietly began writing a body of starkly original folk songs under the name Connie Converse, recording them at home on a Crestwood 404 reel-to-reel recorder. Later she met the artist Gene Deitch, who began recording Converse himself, struck by her spellbinding alto and strange, sophisticated songs about loneliness, freedom, and self-realization. More than half a century later, Deitch’s 1950s recordings would become How Sad, How Lovely—the first collection of Converse’s songs, released in 2009. Unearthed along with the music was an unsolved mystery: In 1974, Converse packed her belongings into her Volkswagen Beetle, left a message to her loved ones asking them not to look for her, and disappeared without a trace, never to be seen again. Though her songs remained unheard until the 2000s, Converse’s intensely intimate DIY songwriting anticipated generations of folk singers to follow, from Joni Mitchell to Karen Dalton to Angel Olsen. Themes of loneliness loom large, though almost never as a negative: “We lived alone/My house and I/We had the earth/We had the sky,” she trills on “We Lived Alone,” while “Roving Woman” finds rollicking humor in an unusually itinerant life. Nearly lost to history, Converse’s songs live on in this expanded reissue by Third Man Records, which features a new remix of “Playboy of the Western World” and a previously unheard original track, “House.”