In the mid-1960s a twenty-something Hunter S. Thompson was just beginning his savage rise to literary stardom. Hells Angels had just been published and after several grueling years freelance writing, Thompson was attracting the attention of national magazines, publishers and agents.
In the summer of 1967 Playboy editor John Grabree contacted Thompson's Random House publicist, Selma Shapiro, about writing for Playboy. The two exchanged letters for a year, discussing various story ideas about hippies, Haight-Ashbury, the rise of Jefferson Airplane and a Scottish gamekeeper claiming to be a werewolf. Thompson was eventually commissioned to write about U.S. Olympic skier Jean-Claude Killy, and the subsequent endorsement contracts he was offered after winning Olympic gold medals. The article, however, became snared in an ugly revision process and never made it into print.
Having worked tirelessly on the piece, the experience briefly soured Thompson's relations with Playboy. Scanlon's Monthly would go on to publish the article, The Temptations of Jean-Claude Killy in the March 1970 issue. In a December 1969 letter from Hunter’s second volume of letters, Fear and Loathing in America: The Brutal Odyssey of an Outlaw Journalist, Hunter writes to the editor of Scanlon’s Monthly shortly after Playboy had decided to kill the piece:
"Some people dig it for the word-action; others hate it for the style and tone. The editors of Playboy really despised it: Their edit/memos ranged from “This is a good Esquire piece” to “Thompson’s ugly, stupid arrogance is an insult to everything we stand for” and “This is our last adventure with H. Thompson; from now on we’ll read his prose in book-form, or not at all…."
Thompson and Playboy's relations began to thaw in the early 1970s when Thompson was contacted by Playboy editor David Butler about writing a piece about a fishing competition in Cozumel, Mexico. The article, The Great Shark Hunt, eventually was published in Playboy's December 1973 issue and became the title story of his 1979 anthology of articles and essays, The Great Shark Hunt. Thompson's correspondences with Playboy document a burgeoning relationship at the height of his journalistic prowess. The handwritten addenda, feverishly scrawled on Woody Creek and Rolling Stone magazine stationary offer a fleeting glimpse into the life of not just Hunter S. Thompson, the drug-addled gonzo legend—but Hunter S. Thompson, the diligent, acerbic and always off-color journalist.