In 1958, Hunter S. Thompson applied for a job with the Vancouver Sun. He was fresh out of 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.
Read the full letter below.
TO JACK SCOTT, VANCOUVER SUN
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.
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.
Hunter S. Thompson
Note: An earlier version of this post appeared on our site in April 2015.
Jonathan Crow is a Los Angeles-based writer and filmmaker whose work has appeared in Yahoo!, The Hollywood Reporter, and other publications. You can follow him at @jonccrow. And check out his blog Veeptopus, featuring lots of pictures of badgers and even more pictures of vice presidents with octopuses on their heads. The Veeptopus store is here.