Would You Hire These Famous People Based On Their Former Job Applications?

Could you be passing over the next Hunter S. Thompson or Madonna? These famed artists and writers had to start somewhere.

Would You Hire These Famous People Based On Their Former Job Applications?
[Image: Flickr user Kathryn Decker]

Everyone has to start somewhere. Even the rich and famous often come from humble beginnings. Jennifer Hudson worked at Burger King. Jon Bon Jovi made Christmas decorations. Demi Moore was a debt collector. Before they were famous, they were just trying to make a buck.


Without the credibility of success, one can’t help but wonder what the best and brightest minds might have looked like to potential employers. Would you have hired them? You be the judge.

Below are excerpts from four job applications from famous people before they made it, with some hiring expert insight into what they’re doing right and wrong.

Image: JoJan via Wikimedia Commons


Leonardo da Vinci

Our first job application dates back to the 1480s. A 32-year-old Leonardo da Vinci was trying to get a job working for Ludovico Sforza, the then ruler of Milan.

“My Most Illustrious Lord,” he begins–not exactly the kind of language you’d find on a cover letter these days. But da Vinci goes on to offer a numbered list of 10 skills ranging from: “plans for very light, strong and easily portable bridges with which to pursue and, on some occasions, flee the enemy” to ” methods for destroying every fortress or other stranglehold unless it has been founded upon a rock or so forth” to “means of arriving at a designated spot through mines and secret winding passages constructed completely without noise, even if it should be necessary to pass underneath moats or any river.”

Only after his exhaustive list of 10 almost superhuman skills, does da Vinci mention his biggest strengths: “I can execute sculpture in marble, bronze and clay. Likewise in painting, I can do everything possible as well as any other, whosoever he may be.”


Da Vinci was hired and eventually commissioned by Sforza to paint “The Last Supper.” But what can we learn from his job application?

“The problem with it is that it’s not targeted,” says Dan Schawbel, author of the book Promote Yourself and managing partner of the New York-based consulting firm, Millennial Branding. Still, adds Schawbel: “Bullet points and numbering is actually pretty effective,” especially since people spend about eight seconds on a resume.

Even 500+ years ago, da Vinci was onto something when it came to resume writing.


Eudora Welty

In 1933, an inexperienced 23-year-old Eudora Welty wrote to The New Yorker asking for a job. She would go on to become a Pulitzer Prize-winning novelist, but at the time she was just another hopeful looking to break into the magazine world. From her cover letter:

“I suppose you’d be more interested in even a sleight-o’-hand trick than you’d be in an application for a position with your magazine, but as usual you can’t have the thing you want most,” she opens the letter. She then offers a rundown of her background and time in New York – “six weeks on the loose.”

Welty goes on to list some of what she’s got to offer:


“As to what I might do for you–I have seen an untoward amount of picture galleries and 15¢ movies lately, and could review them with my old prosperous detachment, I think; in fact, I recently coined a general word for Matisse’s pictures after seeing his latest at the Marie Harriman: concubineapple. That shows you how my mind works–quick, and away from the point. I read simply voraciously, and can drum up an opinion afterwards.”

And a shot of her enthusiasm for the job:

“How I would like to work for you! A little paragraph each morning–little paragraph each night, if you can’t hire me from daylight to dark, although I would work like a slave. I can also draw like Mr. Thurber, in case he goes off the deep end. I have studied flower painting.”


The New Yorker didn’t hire Welty. What did she do wrong? “She talks about herself too much and not enough about the employer,” says Schawbel.

Of course, The New Yorker did go on to publish Welty’s stories down the line and she won much recognition for her work, including a 1973 Pulitzer Prize.

Image: MDCarchives via Wikimedia Commons

Hunter S. Thompson

In 1958, Hunter S. Thompson applied for a newspaper job at the Vancouver Sun. If you’ve read any of his work, the brazenness of his cover letter should not surprise you. Still, is it the kind of thing that could score him (or anyone for that matter) a job?


Thompson’s cover letter is unabashed in its frankness:

“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.”

What’s more, he isn’t afraid to fess up to his bad rep with former employers:

“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.”

He’s also not afraid to badmouth the industry:

“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.”

From the perspective of a hiring manager today? “There’s too much rambling,” says Schawbel. “He put down the industry he wants to get into, which comes down as very negative.”


Of course it’s that very attitude that earned Thompson his writing fame. But for a first impression job applicant–maybe not the best approach.

Image: Flickr user David Shankbone


Before she made it to icon status, Madonna Ciccone was a drummer from Detroit. When she was 20, she handwrote a three-page letter, applying for a role in the low-budget erotic thriller A Certain Sacrifice.

“Please excuse the informal resumé,” she wrote in her bubbly cursive. “I have been out of the country for several months and upon returning discovered many important papers misplaced. My resumés included.”


She then goes on to detail the story of her life from birth to fifth grade to being a college dropout. And ends:

“After 2 months of restaurants & nightclubs everyday, being dragged to different countries every week and working with business men and not musicians I knew this life was not for me. I hung out in Paris for one more month, feeling miserably unproductive, but I couldn’t bear the Parisian sterility or my homelessness any longer, so I came back to N.Y. I’ve been here 3 weeks now, working with my band, learning to play the drums, taking dance classes and waiting for my 20th birthday.

Is this all?”

Good thing for her career, the answer was a resounding, “No.”


About the author

Jane Porter writes about creativity, business, technology, health, education and literature. She's a 2013 Emerging Writing Fellow with the Center For Fiction