Disillusionment and Discord (1962-1965)

Holiff had an ambitious vision for Cash's career. He was certain that Cash could play the most prestigious venues in the world and attain a superstar status comparable to that of Elvis Presley, Cash's old friend from Sun Records.

Cash and Presley's careers so far had followed similar trajectories: they had both been signed by Sam Phillips at Sun in the early 1950s and produced hits that gained popular attention and ranked high on the country and pop charts. But Presley had more successfully established himself as a crossover artist, and Holiff insisted that this was what Cash had to do as well.

(Incidentally, Presley and Cash were both managed by Bob Neal before switching managers--in Presley's case, to Colonel Tom Parker; in Cash's, to Stew Carnall, then Holiff--just as they started to achieve serious success.

Parker was arguably the most influential manager in music history, his notoriety typified by his status as Colonel Tom Parker. Not one to be outranked, Holiff secured himself a Kentucky colonelcy in 1973.)

To this end, Holiff coined the term "Americana's Most Wanted Singin' Storyteller" for Cash, seeking to market him as a unique performer who told stories of American culture in song.

Holiff also booked major shows for Cash at Carnegie Hall in New York City and the Hollywood Bowl in Los Angeles. As Hilburn explains, “Carnegie Hall and the Hollywood Bowl were part of Holiff’s master plan to reposition Cash, in the eyes of disc jockeys and talent bookers, from a country music singer to a folksinger with strong mainstream appeal. If he could do that, Holiff figured he’d have a much better chance of getting his client booked on primetime TV shows and into the more lucrative pop market” (226).

As a venue in which no country artist had ever headlined a show before, Carnegie Hall in particular was, according to an interview with Holiff in the documentary Half a Mile a Day (2000), an "attempt to make him a one of a kind." For Holiff, these shows were intended to "set him aside" by making Cash "a distinct entity in Nashville" and catapulting him to unprecedented success.

The key to pulling off these shows was scale. Holiff wanted to put together a grand performance, so he booked Johnny Western to serve as emcee, along with five other acts--including Gordan Terry and George Jones, who often toured with Cash--to support Cash as the headliner. June Carter, along with her mother, Maybelle, and sisters, Anita and Helen, were on the bill as well. For the show at Carnegie Hall, Holiff--who was not only trying to get Cash on the pop charts but also sought to market him as a folk act--saw the potential to capitalize on the Carter Family name, which was synonymous with the American folk tradition.

Pulling off the show was a coup for a new manager, and Holiff planned it with an eye to posterity. He advertised the show heavily, commissioned elegant programs in black and silver for fans to purchase as souvenirs of the show (typical of Holiff's branding, the program inside reads "Saul Holiff presents"), and arranged with Don Law, Cash's producer at Columbia Records, to record a live album of Cash's performance. With Holiff's meticulousness in booking and promoting the show, Carnegie Hall should have been a triumph for Cash's career.