Best and Worst College Application Essay Prompts, Supplements and Common App Questions

As the college application essay writing season draws to a close, with only a short time left before most regular applications are due, I'm looking back on some of the most interesting -- and most annoying -- essays prompts I've seen this year.

I'm also taking a moment to marvel at how revealing the essay prompts are about what kind of students the colleges are looking for when they devise the questions that help them distinguish between tens of thousands of applicants. Precisely because there are so many hugely accomplished, talented students, and because the Common Application has devoted itself to making it easy to apply (and increasing its own coffers in the process, let's not forget), the essays are one of the tools used by the schools to make distinctions. And the essay questions, which vary enormously from institution to institution, tell us some of what each institution values in its applicants.

The University of Chicago's famously demanding, quirky prompts are there to help them select the kind of students who would thrive in this highly cerebral atmosphere. By the same token, the essay prompts are information for the applicants, too. If you're not comfortable writing an essay inspired by this prompt: "Joan of Arkansas. Queen Elizabeth Cady Stanton. Babe Ruth Bader Ginsburg. Mash up a historical figure with a new time period, environment, location or occupation, and tell us their story," it's a safe bet that this isn't the right university for you. I frequently have clients who are eager to apply there, until they read the prompts.

Cornell University's College of Arts and Sciences, by contrast, asks a straightforward question that is demanding in a very different way. It requires a lot of intellectual curiosity and deep study of Cornell's course catalog and curriculum, and it can be up to 650 words long, not the 100 or 150 words that the usual Why This College question usually is. The word count is a tip-off that Cornell wants a thorough answer: "Describe two or three of your current intellectual interests and why they are exciting to you. Why will Cornell's College of Arts and Sciences be the right environment in which to pursue your interests?"

Tufts' several supplementary essays are demanding in an entirely different way. Pomona's prompts are looking for precise evidence of critical thinking, while Barnard's are going in search of a candidate's fearlessness and interest in women of accomplishment.

It's hard to choose my favorite of the essay prompts I encountered this year, but easy to choose the one I thought the most off-putting. That prize goes to the University of Rochester: "Students here who thrive in white winters wonder how can you make Rochester 'ever-cooler'?"

In general, I'm partial to accentuating the positive in these matters, but it rankles me every time I read it. It sounds as though whoever came up with it -- a dean, a PR firm? -- was working too hard to make the University of Rochester sound "cool." The idea that "students" are looking for the "ever-cooler" applicants, rather than the Office of Admissions, is condescending.

And who cooked up the hopelessly uncool expression "ever-cooler"? It's not in the Urban Dictionary. None of the students I worked with had ever heard it, and they all scratched their heads about how to answer. As with most of these questions, the universities want to know what makes you stand out, what you'll bring to the place that's unique, what might be your best qualities or your most passionate interests. Let's just say that that's probably what they're getting at. My suggestion was to answer by talking about a unique quality or interest you have -- never mind who thinks it's "cool" or "ever-cooler."

Why does a university end up with a question like this? They admissions people want to attempt to stand out by asking a slightly off-beat question. They want to see what kind of answer a student will give to a question that isn't straightforward. Perhaps they even want to limit applications, by asking a question that might turn applicants off -- and thereby keep only the most serious students applying. It's hard to know. I'll be looking next summer to see if they keep this prompt.

My favorite prompts go to Barnard, Colorado College, Lehigh, Tufts, University of California and the University of Chicago, and I'm fond of Prompt 4 on the Common Application Essay. I like them because they're open-ended inquiries that students can make their own. They can answer in ways that reveal who they are, whether they're highly academic, highly creative, science nerds, music lovers and anything in between. I also want to single out a few top colleges and universities that have figured out how to distinguish between students without using any supplementary essays at all: Middlebury, Wesleyan and Washington University.

Here are my favorites, in alphabetical order:

Barnard: "Pick one woman in history or fiction to converse with for an hour and explain your choice. What would you talk about?"

Colorado College: "Design your own three-and-a-half week course and describe what you would do."

Lehigh: "What do you and Lehigh have in common?"

Tufts: "What makes you happy?"

University of California: "Describe the world you come from -- for example, your family, community or school -- and tell us how your world has shaped your dreams and aspirations."

University of Chicago: "Orange is the new black, fifty's the new thirty, comedy is the new rock 'n' roll, ____ is the new ____. What's in, what's out and why is it being replaced?"

Prompt 4, Common Application: "Describe a problem you've solved or a problem you'd like to solve. It can be an intellectual challenge, a research query, an ethical dilemma -- anything that is of personal importance, no matter the scale. Explain its significance to you and what steps you took or could be taken to identify a solution."

I'd love to hear from you about what prompts have been your least favorite and your most favorite from this year or previous years -- and why?

Elizabeth Benedict is the founder of Don't Sweat the Essay and the author of five novels and a classic book on writing fiction. She tweets at @ElizBenedict.