Hunter S. Thompson was just 22-years-old in 1959 when he first began writing The Rum Diary, or what he initially called "the great American rum novel." He envisioned it as something of a contemporary and rum-soaked version of The Great Gatsby, one of Thompson's favorite books. Based on the time Thompson spent working for an English language newspaper in San Juan, Puerto Rico, The Rum Diary fictionally chronicles the drunken and debauched life of Paul Kemp, an American journalist sauntering through San Juan with a savage lust for women, blood and booze. Once finished, Thompson spent nearly a decade revising and shopping it to publishers before reverting to other projects. It wasn't until 1998 that Thompson was finally able to publish The Rum Diary.
Now, more than a decade later Thompson's great American rum novel will make its way to the big screen Oct. 28, starring Johnny Depp as Paul Kemp and Amber Heard as Kemp's enigmatic love interest, Chenault. Celebrating yet another milestone in Thompson's ever-growing list of achievements, we've gathered some of Thompson's most memorable stories from Playboy magazine in one place on Playboy.com and have curated the iPlayboy "On Beyond Gonzo" Commission of Thompson-inspired pieces and articles featuring the savage illustrations of Ralph Steadman.