Model Cover Letter… Not!

As a humorous but also totally serious model of what not to send to a potential employer, I submit Hunter S. Thompson’s letter to the Vancouver Sun from 1958.


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


Now that we’ve had a good laugh, let’s talk about cover letters in general. As a rule, I don’t think they are necessary when you work with a good recruiter because the recruiter IS the cover letter (for more information on when a cover letter is not necessary, click here). However, when applying to a position through an ad, a cover letter is what fleshes out the CV and is important. As we review the worst cover letter ever written (see above) let’s pull out some key problems with this letter.

Hubris ( h)yo͞obrəs/- excessive pride or self-confidence): This is the biggest flaw throughout the whole letter. The other problems pale in comparison but we will address them as well. No employer responds positively to arrogance in a cover letter. You must strike a delicate balance of industry knowledge / confidence, and a humble, factual presentation of specific skills matching what the company is seeking in an applicant. Resonance of humility without diminishing your strengths is ideal.

NEVER bad-mouth your former boss place or of employment! This is the child of arrogance and has the same result of leaving a bad taste in the mouth of those who hear or read it. This may seem like a no-brainer, but let me spell it out – speaking badly about a former boss makes you look unprofessional and causes a potential employer to worry that they may become the focus of your badmouthing in the future. Most of us have had negative employment experiences, but keep your emotions in check. If you want to get that face to face interview then in your cover letter (and phone interview) keep your statements about past employment professional and respectful, focusing on the positive only.

Over-reliance on Humor: An upbeat attitude, yes. Hints at humor showing you’re no Debbie Downer, perhaps. But sarcasm and sardonic humor are unlikely to attract a good employer. Best to be specific and clear, allowing your skills and experience to stand out versus your sense of humor.

Lack of Specifics! In his cover letter, Mr. Thompson unabashedly positions himself as an expert in his field but in truth Mr. Thompson had done little more than sports writing for his high school. A cover letter needs to be truthful in every detail. Otherwise, if discovered, one small fabrication or exaggeration will undermine the veracity of the whole document. Determine the skills and experiences that specifically qualify you for the job to which you’re applying and flesh out, in detail, your strengths.

While we all enjoy reading this cover letter we can all agree that it would not compel us to interview Mr. Thompson.  For more about when a cover letter is important, click here.

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