Hunter S Thompson

Cracker letter! Hunter S Thompson's cover letter applying for a job at the Vancouver Sun in 1958.
Read it here.
Whether it worked or not, it was a stepping stone in Thompson's legend as reporter, author (Fear and Loathing in Las Vegas, Hells Angels) and founder of 'Gonzo journalism' - a subjective style of journalism whereby the writer insinuates himself into the story.
The letter was sent to the editor, Jack Scott, who was famous for spectacular stunts in the newsroom - sending the women's page editor to Cuba to cover the revolution and the sports guy to Formosa to interview the leader of the Republic of China. 
Perhaps unsurprisingly, Scott had a brief but formidable reign...would love to have seen his response to Thompson's letter.