All but one of the letters mentioned here come from the recently published book Letters of Note: An Eclectic Correspondence Deserving of a Wider Audience, an anthology of Shaun Usher’s wonderful blog of the same name. It’s well worth picking up.

Cut Through the Noise

The trouble with most cover letters is that they sound canned. Using boilerplate formalities won’t make you sound serious; it will just make it harder to tell one cover letter from another. Use your personality, even if it means channeling your anxieties about the job you hope to get. For instance, Eudora Welty opened with a bit of disarming humor when she applied for a job at The New Yorker in 1933 as an unknown 23-year-old writer with no experience:

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.

And she closes with a self-deprecating joke and an amazing pun:

There is no telling where I may apply, if you turn me down; I realize this will not phase you, but consider my other alternative: the U of N.C. offers for $12.00 to let me dance in Vachel Lindsay’s Congo. I congo on.

Both you and the person reading your application know that you’re engaged in a dull little ritual. Anything to break up that monotony is likely to get you noticed.

Be Specific About Your Skills

Da Vinci’s letter to the ruler of Milan, Ludovico Sforza, overwhelms the reader’s defenses with details of his war-waging abilities, from constructing secret subterranean passageways to designing “very beautiful” cannons and catapults:

1. I have plans for very light, strong and easily portable bridges with which to pursue and, on some occasions, flee the enemy, and others, sturdy and indestructible either by fire or in battle, easy and convenient to lift and place in position. Also means of burning and destroying those of the enemy.

and

4. I have also types of cannon, most convenient and easily portable, with which to hurl small stones almost like a hail-storm; and the smoke from the cannon will instil a great fear in the enemy on account of the grave damage and confusion.

Welty’s talents were less martial but equally impressive:

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.

Try to Show Your Skills in Action

It’s one thing to say you can do the job; quite another to show it. In 1934, Robert Pirosh was a young copywriter who wanted to break into Hollywood. The brief cover letter he sent to directors vouches for his abilities better than a lengthy CV could:

I like words. I like fat buttery words, such as ooze, turpitude, glutinous, toady. I like solemn, angular, creaky words, such as straitlaced, cantankerous, pecunious, valedictory. I like spurious, black-is-white words, such as mortician, liquidate, tonsorial, demi-monde.

And so on for another 100 or so peregrinating, bravura, gurgling words. Pirosh was hired as a junior writer for MGM, where he wrote for the Marx brothers and won an Academy award for Battleground.