In the late 1960s, Leon teamed up with guitarist Marc Benno to form The Asylum Choir. The two went on to record a pair of albums that, while never commercial successes, became critical darlings and blueprints for the kind of musical trailblazer Leon would become over the course of his career. Rolling Stone magazine called the duo's debut album, "Vital, Freaky, and Exciting," and went on to name the album one of its 20 Albums Rolling Stone Loved in the Sixties That You've Never Heard

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After their 1968 initial release on Smash records, the two would go their separate ways, with Leon going on to pursue solo work and Benno adding to his resume as a session guitarist with performances on The Doors "L.A. Woman" album. Their second recording was released in 1972, a few years after their disbanding. Leon released it on his own label, Shelter Records, and it went on to peak at #70 on the Billboard 200, in large part due to the success that Leon had found in his solo career.