Most people try to be as polite and flattering as possible when writing a prospective employer to ask for a job. It's really the only medium where being obsequious is seen as a virtue. But when Hunter S. Thompson applied for a job at the Vancouver Sun in 1958, the famously wild and inventive author wrote a cover letter that, like Thompson himself and the "gonzo journalism" that would make him famous, broke all the rules. He is insulting, dismissive, narcissistic ("don't think that my arrogance is unintentional"), and trumpets as his greatest asset the fact that his editor wrote a formal letter to the publisher complaining of the young journalist's behavior. In short, classic Thompson. Here's the letter:
The Ottawa Citizen's Andrea Woo adds, "In 1958, Thompson was still a struggling journalist, living in a tiny basement apartment in New York's Greenwich Village, burdened by crippling debt. ... Self-professed to be in a 'frenzy of drink,' Thompson penned a letter of application to the Vancouver Sun. He had heard about the paper through an article in Time magazine — where he worked briefly as a copy boy for $50 U.S. a week — that praised the paper's new editorial direction under Jack Scott."
Thompson never got that job at the Vancouver Sun, but he did go on to pioneer a wholly new style of first-person journalism, exemplified by such reportage as the 1970 masterpiece "The Kentucky Derby is Decadent and Depraved" (which you can read here), which is not a bad concession.