Hunter S. Thompson for sheriff!

"In 1970 Thompson ran for sheriff of Pitkin County, Colorado, as part of a group of citizens running for local offices on the "Freak Power" ticket. The platform included promoting the decriminalization of drugs (for personal use only, not trafficking, as he disapproved of profiteering), tearing up the streets and turning them into grassy pedestrian malls, banning any building so tall as to obscure the view of the mountains, and renaming Aspen "Fat City" to deter investors. Thompson, having shaved his head, referred to his opponent as "my long-haired opponent", as the Republican candidate had a crew cut.

With polls showing him with a slight lead in a three-way race, Thompson appeared at Rolling Stone magazine headquarters in San Francisco with a six-pack of beer in hand and declared to editor Jann Wenner that he was about to be elected the next sheriff of Aspen, Colorado, and wished to write about the Freak Power movement.[15] Thus, Thompson's first article in Rolling Stone was published as The Battle of Aspen with the byline "By: Dr. Hunter S. Thompson (Candidate for Sheriff)." Despite the publicity, Thompson ended up narrowly losing the election. While actually carrying the city of Aspen, he garnered only 44% of the county-wide vote in what became a two-way race as the Republican candidate for sheriff agreed to withdraw from the contest a few days before the election in order to consolidate the anti-Thompson votes, in return for the Democrats withdrawing their candidate for county commissioner. Thompson later remarked that the Rolling Stone article mobilized his opposition far more than his supporters."

Source: http://en.wikipedia.org/wiki/Hunter_S_Thompson