Application Essay Tips from a Broadway Lyricist

With three little sisters who love musical theater, and long car rides on summer vacations to drill song lyrics into my head, I suppose turning to Hammerstein for application essay tips was inevitable. I know more musical theater lyrics than I care to admit, so I won’t. Today's application essay tips come from Hammerstein's essay entitled "Happy Talk."

6 Application Essay Tips Courtesy of Oscar Hammerstein II

What application essay tips can we learn from Hammerstein’s essay? Here are six to consider:

Application Essay Tips | Tip #1: Mix short and long sentences.

In the first paragraph, Hammerstein opens with four short sentences and finishes with two longer ones. The second paragraph opens with a long sentence and finishes with several short ones. As you read the essay, note how Hammerstein varies sentence length to keep the essay moving. When you write your essay, you’ll want to mix short and long sentences, too. Otherwise, an essay of short sentences gets choppy, and an essay of long sentences gets unreadable.

Application Essay Tips | Tip #2: Ask the reader a question.

In the first paragraph, Hammerstein states, “I am a man who believes he is happy.” In the second paragraph, to follow up on his initial statement, Hammerstein asks, “Why do I believe I am happy?” A thoughtful question – by which I mean a question that the reader is already asking herself – engages the reader. In a previous post on application essay tips, I compared the application essay to a monologue. But unlike an actor performing a monologue, you, the essay writer cannot see the audience and confirm the reader is paying attention. Asking the reader a question can help you connect with your unseen reader.

Application Essay Tips | Tip #3: Use contrasting language.

Hammerstein makes comparisons by using contrasting language. For example, he writes, “It is a modern tragedy that despair has so many spokesmen, and hope so few.” The contrast is between the “so many” spokesmen of despair and the “so few” spokesmen of hope. He could have omitted “and hope so few” from the sentence, but doing so would weaken his comparison.

Later, Hammerstein writes, “You cannot isolate virtue and beauty and success and laughter, and keep them from all contact with wickedness and ugliness and failure and weeping.” The contrast is between the four good things in the sentence’s first half and the four opposing bad things in the sentence’s second half. Virtue is the opposite of wickedness, beauty the opposite of ugliness, success the opposite of failure, and laughter the opposite of weeping. The listing of opposite concepts strengthens Hammerstein’s comparison. When you make a comparison in your essay, consider how to employ contrasting language.

Application Essay Tips | Tip #4: Use a simile.

A simile is a comparison that uses “like” or “as.” Hammerstein writes that arguing he is unhappy would be creating a “false picture, as false as if I were to describe a tree only as it looks in winter.” This simile succeeds for two reasons. First, it refers to an image we all understand: a tree as it looks in winter. Second, it is original. “Dumb as a doorknob” is a simile with a clear image, but because it is a cliché, you do not want to use it. Be creative, and choose an original yet familiar image.

Application Essay Tips | Tip #5: Use repetition.

The more I read these essays, the more I decide that repetition is one of my favorite things. Consider how Hammerstein uses “have disappointed” at the end of the second paragraph or “I would be leaving…” in the third. Why not make your life easy? Once you find a sentence structure you like, repeat it.

Application Essay Tips | Tip #6: Be optimistic.

Hammerstein writes about being happy, but he does not pretend every moment is happy. Instead, he acknowledges his imperfection before resolving not to allow it to destroy his hope. Optimism indicates maturity because it shows you can identify the instructive aspect of your experience. (Naturally, I say this as someone who was previously the most pessimistic person I knew.)

Think about what type of students colleges want. Do they want complainers or blamers or whiners? No. So try not to write like one. You do not have to pretend every moment of your life is happy, but whatever topic you choose, at least put a positive spin on it. You had a challenge, but you overcame it (or maybe you didn’t, which is fine), and you learned something in the process.

Enjoy Hammerstein’s essay, and see if you agree that it suggests some application essay tips you can use. If you liked today's application essay tips, please recommend them to your friends. Thank you!


Jon Perkins holds a B.A. in English from Stanford University and a J.D. from Harvard Law School. He helps students with their college, law school, and medical school applications.