Rum Diary, The
In fact, Thompson was only 22 when he wrote The Rum Diary, but his fear of winding up like Moberg was well founded. What saved him was the fantastic conflagration of the 1960s, a fiery wind on which the reptilian wings of his prose style could catch and soar to the cackling heights of Fear and Loathing in Las Vegas. Puerto Rico in 1959 doesn't have bad craziness enough to offer Thompson--just a routine drunken-reporter stomping by local cops and a riot over Kemp's friend's temptress girlfriend, a scantily imagined Smith College alumna who likes to strip nude on beaches and in nightclubs to taunt men.
Thompson's prose style only intermittently takes tentative flight--compare the stomping scenes in this book with his breakthrough, Hell's Angels--but it's interesting to see him so nakedly reveal his sensitive innards, before the celebrated clownish carapace grew in. It's also interesting to see how he improved this full version of the novel from the more raw (and racist) excerpts found in the 1990 collection Songs of the Doomed (available on audiocassette, partly narrated by Thompson). --Tim Appelo