Career advice from the great Hunter S. Thompson

In 1958, Hunter S. Thompson applied for a job with the Vancouver Sun. He was fresh out the Air Force and struggling to make a living in New York City, though from the tone of the letter you wouldn’t know it.

People who are experts in such things say that good cover letters should match the employer’s needs with the applicant’s abilities, should be tailored specifically to the job in question and should show some personality. By those yardsticks, Thompson’s letter to the Vancouver Sun is a model to be followed. He lays out his eagerness to work: “I can work 25 hours a day if necessary, live on any reasonable salary.” Any HR manager would be tickled with lines like that. He succinctly describes his work experience: “most of my experience has been in sports writing, but I can write everything from warmongering propaganda to learned book reviews.” And for any other fault you might find with the letter, it definitely doesn’t lack in personality.

Yet the letter somehow failed to charm his would-be employer; Thompson never moved to Vancouver. Perhaps they were given pause by Thompson’s steady stream of insults directed towards his former editor — “It was as if the Marquis De Sade had suddenly found himself working for Billy Graham” — and towards journalism in general: “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.” Or perhaps it was his intentionally off-putting arrogance, “I’d rather offend you now than after I started working for you.” In any case, it’s a hoot to read. More people should write job application letters like this.

October 1, 1958 57 Perry Street New York City 
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....more