In this discussion I want to take seriously Dewey's notions that philosophy grows out of and returns to primary experience and that education as life transformation occurs pervasively outside the settings of formal educational institutions. I also want to take seriously Bruce Springsteen's suggestion that some of us "learned more from a three-minute record than we ever did in school." Using several examples, I want to show the ways in which American philosophical thought both informs and is informed by popular culture; I want to encourage serious exploration of the dialectical relations between the two. Since my own "primary experience" is from an angle of vision that is white, male, rural, and northern, the philosophies and cultural phenomena I employ reflect the same. Thus, my examples are meant only to be "representative" in an Emersonian way; that is, they are not meant as exemplary but as openings to conversations with others whose histories and perspectives are different. Among those who work philosophically in this way I would include bell hooks, John McDermott, and Gloria Anzaldua. The three examples I will use to initiate discussion are the relationship between Dewey's focus on qualitative immediacy and a kind of male mysticism to be found in Springsteen's "Born to Run"; Thoreau's emphasis on a need for wildness and examples of wildness gone awry in the lives of male country musicians, using Tammy Wynette's "Stand by Your Man" as a point of departure; and, time permitting, the respective 19th and 20th century quests for "transcendence" in experience by Emerson through an emphasis on the future and by Jack Kerouac through an emphasis on memory. Again, the aim of the examples will be to initiate conversations that look elsewhere in popular culture for philosophically-minded work.