Back in January, when I asked high school seniors to send in college application essays about money, class, working and the economy, I wasn’t sure what, if anything, would come in over the transom.

But 66 students submitted essays, and with the help of Harry Bauld, the author of “On Writing the College Application Essay,” we’ve selected four to publish in full online and in part in this column. That allowed us to be slightly more selective than Princeton itself was last year.

What these four writers have in common is an appetite for risk. Not only did they talk openly about issues that are emotionally complex and often outright taboo, but they took brave and counterintuitive positions on class, national identity and the application process itself. For anyone looking to inspire their own children or grandchildren who are seeking to go to college in the fall of 2014, these four essays would be a good place to start.

Perhaps the most daring essay of all came from Julian Cranberg, a 17-year-old from Brookline, Mass. One of the first rules of the college admissions process is that you don’t write about the college admissions process.

But Mr. Cranberg thumbed his nose at that convention, taking on the tremendous cost of the piles of mail schools send to potential students, and the waste that results from the effort. He figured that he received at least $200 worth of pitches in the past year or so.

“Why, in an era of record-high student loan debt and unemployment, are colleges not reallocating these ludicrous funds to aid their own students instead of extending their arms far and wide to students they have never met?” he asked in the essay.

Antioch College seemed to think that was a perfectly reasonable question and accepted him, though he will attend Oberlin College instead, to which he did not submit the essay.

“It’s a bold move to critique the very institution he was applying to,” said Mr. Bauld, who also teaches English at Horace Mann School in New York City. “But here’s somebody who knows he can make it work with intelligence and humor.”

Indeed, Mr. Cranberg’s essay includes asides about applicants’ gullibility and the college that sent him a DHL “priority” envelope, noting inside that he was a priority to the college. “The humor here is not in the jokes,” Mr. Bauld added. “It originates in a critical habit of mind, and the kind of mind that is in this essay is going to play out extremely well in any class that he’s in.”

Admissions professionals often warn people not to think that they can write their way into the freshman class. “The essay is one document that, even in the best of circumstances, is written by an individual telling one story,” said Shawn Abbott, the assistant vice president for undergraduate admissions at New York University. “I don’t believe that any one writing sample should trump what they did over four years.”

Still, he acknowledged that his staff had been taken with the story told by Lyle Li, a 19-year-old Brooklyn resident who applied this year. He wrote about his family’s restaurant and his mother, an immigrant from China who once wanted to be a doctor and now works behind a cash register.

“When I visit my friends, I see the names of elite institutions adorning the living room walls,” wrote Mr. Li, a senior at Regis High School in Manhattan. “I am conscious that these framed diplomas are testaments to the hard work and accomplishments of my friends’ parents and siblings. Nevertheless, the sight of them was an irritating reminder of the disparity between our households. I was not the upper-middle-class kid on Park Avenue. Truth be told, I am just some kid from Brooklyn. Instead of diplomas and accolades, my parents’ room emits a smell from the restaurant uniforms they wear seven days a week, all year round.”

Twitter: @ronlieber