Essay Questions: Where’s Waldo?

The University of Chicago is renown for their applications’ essay questions. This year one option is “So where is Waldo, really?”

Here are ten prompts from the past:

  1. Find X.
  2. How did you get caught?
  3. “Don’t play what’s there, play what’s not there.” (Miles Davis)
  4. What do pictures want?
  5. “The only interesting answers are those that destroy the questions.” (Susan Sontag)
  6. “I do not know which of us has written this page.” (Jorge Luis Borges)
  7. “The instructor said,
    Go home and write
    a page tonight
    and let that page come out of you -- 
    then it will be true." (Langston Hughes)
  8. How do you feel about Wednesday?
  9. “Mind that does not stick.” (Zen Master Shoitsu, 1202-80)
  10. Modern improvisational comedy had its start with the Compass Players, a group of University of Chicago students who later formed the Second City comedy troupe. Here is a chance to play along. Improvise a story, essay, or script that meets all of the following requirements:
    • It must include the line “And yes I said yes I will Yes” (Ulysses, by James Joyce).
    • Its characters may not have superpowers.
    • Your work has to mention the University of Chicago, but please, no accounts of a high school student applying to the University—this is fiction, not autobiography.
    • Your work must include at least four of the following elements: a paper airplane, a transformation, a shoe, the invisible hand, two doors, pointillism, a fanciful explanation of the Pythagorean Theorem, a ventriloquist or ventriloquism, the periodic table of the elements, the concept of jeong, number two pencils.