Actor Johnny Depp is reportedly docked outside of Puerto Rico on a 156-foot yacht, shooting an adaptation of the Hunter S. Thompson‘s novel, “The Rum Diary.”

During a recent trip to Puerto Rico, one GalleyCat editor re-read the book and explored vintage footage of the island. This video essay retraces Thompson’s footsteps around 1959, when he struggled as a reporter at a Puerto Rican newspaper–long before his famous drug-fueled reporting during the late 1960s and 70s.

Literary Traveler describes the period: “Puerto Rico was like another West, where people dreamt of staking out a piece of paradise and getting rich. Young Hunter S. Thompson tried to get a job at The San Juan Star, but was rejected by the editor, William Kennedy, who went on to become a successful writer and recipient of the Pulitzer Prize for his novel, Ironweed. (Despite rejection, the two remained lifelong friends.) Still desperate to get down to San Juan, Thompson accepted a more dubious position at El Sportivo, a fledgling English weekly about sports.”