In this essay, I explore Jewish composer/singer/liturgist Debbie Friedman and her time in Houston (1978-1984) as a crucial moment in the history of Jewish education. Working as a music educator in two area synagogues, Friedman negotiated a changing environment as cantorial training rose to become a mark of communal musical authority. She consequently turned to a rising Jewish education counterculture (in CAJE) that increasingly warmed to popular music as a core part of its agenda. Friedman's mutually beneficial relationship with CAJE ultimately built a like-minded audience for her music, while opening a path for song leaders to rise to national spiritual leadership.