Most of Freedy Johnston’s songs are populated with characters that either seem blithely unaware of their terminal shortcomings or are keenly aware of them and lack the conviction or strength to do anything about them. But the opening line of “Trying to Tell You I Don’t Know” from Johnston’s 1992 sophomore album Can You Fly is as autobiographical and real as a song can possibly get. When he sings, “I sold the dirt to feed the band,” he succinctly describes his painful decision to sell his family’s farm in Kansas in order to continue his music career. It is merely the first revelatory moment in an album that is filled with them.
Johnston is one of the rare singer/songwriters who can make melancholy and alienation seem gorgeous and powerful and appealing. Those gifts were readily apparent on his 1990 Bar/None debut, The Trouble Tree, and were almost impossibly strengthened on the indescribably wonderful Can You Fly. The resultant buzz led to a long-term Elektra association (and Johnston’s most enduring song, “Bad Reputation,” from 1994’s brilliant This Perfect World), but the label seemed incapable of understanding how to market the pithy songwriter and his gently hopeless tales of urban heartbreak. So Johnston finally moved on.
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