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:

TO JACK SCOTT, VANCOUVER SUN

October 1, 1958 57 Perry Street New York City

Sir,

I got a hell of a kick reading the piece Time magazine did this week on The Sun. In addition to wishing you the best of luck, I'd also like to offer my services.

Since I haven't seen a copy of the "new" Sun yet, I'll have to make this a tentative offer. I stepped into a dung-hole the last time I took a job with a paper I didn't know anything about (see enclosed clippings) and I'm not quite ready to go charging up another blind alley.

By the time you get this letter, I'll have gotten hold of some of the recent issues of The Sun. Unless it looks totally worthless, I'll let my offer stand. And don't think that my arrogance is unintentional: it's just that I'd rather offend you now than after I started working for you.

I didn't make myself clear to the last man I worked for until after I took the job. It was as if the Marquis de Sade had suddenly found himself working for Billy Graham. The man despised me, of course, and I had nothing but contempt for him and everything he stood for. If you asked him, he'd tell you that I'm "not very likable, (that I) hate people, (that I) just want to be left alone, and (that I) feel too superior to mingle with the average person." (That's a direct quote from a memo he sent to the publisher.)

Nothing beats having good references.

Of course if you asked some of the other people I've worked for, you'd get a different set of answers.

If you're interested enough to answer this letter, I'll be glad to furnish you with a list of references — including the lad I work for now.

The enclosed clippings should give you a rough idea of who I am. It's a year old, however, and I've changed a bit since it was written. I've taken some writing courses from Columbia in my spare time, learned a hell of a lot about the newspaper business, and developed a healthy contempt for journalism as a profession.

As far as I'm concerned, it's a damned shame that a field as potentially dynamic and vital as journalism should be overrun with dullards, bums, and hacks, hag-ridden with myopia, apathy, and complacence, and generally stuck in a bog of stagnant mediocrity. If this is what you're trying to get The Sun away from, then I think I'd like to work for you.

Most of my experience has been in sports writing, but I can write everything from warmongering propaganda to learned book reviews.

I can work 25 hours a day if necessary, live on any reasonable salary, and don't give a black damn for job security, office politics, or adverse public relations.

I would rather be on the dole than work for a paper I was ashamed of.

It's a long way from here to British Columbia, but I think I'd enjoy the trip.

If you think you can use me, drop me a line.

If not, good luck anyway.

Sincerely, Hunter S. Thompson

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.