Earlier this summer, prospective students around the globe with an interest in the University of Chicago received an email with six unusual essay topics . The writing prompts included references to Oscar Wilde, the Transformer action movies, Susan Sontag, AB’51, and physicist Werner Heisenberg. And this little gem: “So where is Waldo, really?”
The annual release of UChicago’s essay prompts has become an eagerly awaited event — an imaginative exercise that often inspires even more imaginative responses. For many students and alumni, the essay questions help define the College’s wit and sense of intellectual adventure. It’s also a communal undertaking, with the majority of topics coming from current or past College  students.
“We want the students to write about things that don’t show up in a workshop on writing college essays,” said Grace Chapin, senior admissions counselor.
In famous past  essay questions, students have been invited to write how they feel about Wednesday, to find the meaning in the super-sized mustard at Costco, or to invent the history of an object. One essay question was simply, “Find x.” Another asked, “How did you get caught?”
Funny, poignant, thought-provoking and deadly serious essays pour in every fall and winter. Laura Castelnuovo, a second-year from New York City, chose the essay question: “Everyone knows there are two types of people in the world. What are they?” Her answer began like this:
For centuries, one thing has divided the human population like no other: the tomato. No, I don't mean the never-used alternate pronunciation or even the settled debate of fruit vs. vegetable, I mean that in my experiences I have encountered only two types of people: those who love tomatoes and those who hate them. These Newtonian-ly equal and opposing groups can be found at salad bars and dinner tables worldwide, taking their stance. Because when that fruit is sliced, battle lines are drawn.
The essay prompts are chosen from suggestions from current students and recent alumni. More than a thousand people sent in essay questions this year. Andy Jordan, a fourth-year in economics from Doylestown, Penn., has submitted a few questions for consideration since he applied to the College. “I enjoyed writing the essay when I applied in 2008,” Jordan said. “I answered the question with an entire essay of questions.”
His prompt, “Don’t write about reverse psychology,” appeared on the list for the Class of 2016. While this didn’t earn him a free T-shirt or cash prize, he said his friends were impressed.
“A good set of essay questions will give every student a chance to let their voice shine through,” Chapin said. They supplement the Common Application essay, which usually has a broad prompt like “evaluate a significant experience, achievement, risk you have taken, or ethical dilemma you have faced and its impact on you.”
Prospective students are also asked to write an essay explaining why they want to come to UChicago, and to explain some of their favorite books or media. Add those to the “uncommon” essay question and the essay for the Common Application, and each applicant writes a total of four essays.
“We learn a lot by reading these essays,” Chapin said. “You can’t write it the day before it’s due, so we see extremely high-quality writing from the applicants.” The admissions officers read tens of thousands of essays between November and March, seeing the unique personality of each student between the generalities on the Common Application and the thoughtful and often funny essays from the supplement.
Having found a fitting way to tackle the essays soon becomes a source of pride for the students. Hundreds of admitted students have posted their essays to the UChicago Class of 2016 group on Facebook, where they are met with encouragement and delight from fellow students. “It’s always a conversation topic during Orientation Week,” Chapin said. The shared experience lets people who have just met discuss something besides their hometown and course of study.
The tradition behind the unique essay questions is at least 30 years old. A question from 1984 invited the students to imagine themselves as astronauts on Mars, and asked them whether they would prefer to be teleported, molecule by molecule, back to earth, or to be the person running the teleporting machine.
The College Admissions  office usually sees a flood of questions about the essays from applying students as their deadlines approach. This year, the officers created an instant meme for their Tumblr page  with some simple advice: “Keep Calm and Study On.”