"Gypsy Lou" is a story about "a ramblin' woman with a ramblin' mind" who is always bouncing around the country and "leaving' somebody behind." It's a silly, fun song about a wild, rootless woman, sung in the spirit of Woody Guthrie's 1938 song "Gypsy Davy."
"Gypsy Lou" also happened to be a real person.
With her husband Jon Edgar Webb, "Gypsy Lou" Webb owned and operated Loujon Press in New Orleans. That press produced The Outsider magazine, historically significant because it was instrumental in exposing the work of Charles Bukowski, the "Nobel Laureate of Skid Row," a poet and author whose cultural impact has lasted long after his 1994 death.
The Outsider also published notable Beat writers like Jack Kerouac and Lawrence Ferlinghetti. The writers it printed were people who were writing about life on the street and the underclass at a time when such a thing was revolutionary. It was countercultural before that word became widely known.
Gypsy Lou was known as a fierce, uncompromising character. A well-known French Quarter artist named Noel Rockmore called Lou was his muse. The story of Lou and The Outsider is told in the 2007 book The Outsiders of New Orleans: Loujon Press.