What if Hunter S. Thompson applied to work for Don Draper of Mad Men?

If you’ve read Hunter S. Thompson’s cover letter from 1958, and you like Don Draper on Mad Men, you might enjoy my new mashup letter:

To Donald Draper, Sterling Cooper Draper Pryce

November 12, 1964

57 Perry Street

New York City


I got a hell of a kick reading the piece Advertising Age did this week on your new agency. In addition to wishing you the best of luck, I’d also like to offer my services.

Since I haven’t seen any of your new work yet, I’ll have to make this a tentative offer. I stepped into a dung-hole the last time I took a job with an agency I didn’t know anything about (see enclosed portfolio) 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 your latest work. 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 general manager.) 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 portfolio should give you a rough idea of who I am. It’s a year old, however, and I’ve changed a bit since I created those pieces. I’ve taken some writing courses from Columbia in my spare time, learned a hell of a lot about the ad business, and developed a healthy contempt for advertising as a profession. As far as I’m concerned, it’s a damned shame that a field as potentially dynamic and vital as advertising 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 SDCP away from, then I think I’d like to work for you.

Most of my experience has been in sports marketing, but I can write everything from warmongering propaganda to vacuum cleaner copy. 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 an agency I was ashamed of.

It’s a long way from here to Midtown, 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

Would I hire someone who sent a letter like that? I’m not sure… but I’d definitely schedule a phone-screen!

Mashup by Karl Sakas of letter originally published in The Proud Highway: Saga of a Desperate Southern Gentleman, 1955-1967 (Ballantine, 1997), published online at TheFutureBuzz.com.


  1. says

    Dear Hunter,
    Thanks for your letter. Any communication from you always helps me smile and have a chuckle. Not sure if you saw our friend Mr. Depp’s film novella of that trip long ago to a place far away is finally inching its way to a cineplex near you: http://huff.to/oA8KmI.

    Memories from that trip and anything else we ever did are a tad fuzzy. Can’t imagine why, can you?

    :). Martin

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