A high school in the 1970s is the setting of the Richard Linklater film Dazed and Confused. (Universal Studios)

September marks the start of a new academic year, as schools across North America begin their fall terms. New students are consumed with figuring how to get around, remembering their locker combination, dropping classes that start too early in the morning and making new friends — all without appearing as clueless as they feel. Returning students look forward to renewing friendships and getting back to work. And for those who feel perpetually out of place or under-prepared, the first week of school presents an opportunity for improvement, if not reinvention.

(Little, Brown and Company)

For people who haven’t been in school for decades, the first week of September still brings twinges of vestigial excitement. Their alma mater has become a metonym, a metaphorical stand-in for a variety of anxieties and life-altering moments. To them, school is closely attached to feelings of lost youth, early oppression, conformity, a yearning to belong and first love.

It’s no surprise, then, that school is such a popular setting in books, films and even songs. Many fiction writers turn to their own feckless youth for material, be it the boarding school in J.D. Salinger’s The Catcher in the Rye or the medical school in Vincent Lam’s Bloodletting and Other Miraculous Cures. Films like Scent of a Woman and The Emperor’s Club tap into the fetish-dreams many grown-ups have of going to a boarding school with starchy uniforms, an owlish teacher and a roommate who calls you by your last name. Rockers invoke the education system in songs about rebellion (see: School’s Out by Alice Cooper) or as a wardrobe schtick — take Angus Young, the middle-aged guitarist of AC/DC who still rocks out in a schoolboy uniform.

I can’t help thinking that one of the reasons we pine for school is that the quality and quantity of time is (or was) different there. A close friend’s death or a tragic affair hits you harder in youth not only because it’s a first experience, but also because you have more time to mull it over — as you get older and more wrapped up in work, relationships and family, you end up shrugging off many disappointments and heartbreaks because you simply can’t fit them into your schedule. (When people grow nostalgic for their school days, they long not only for their youth and a sense of newness, but for all that free time.)

In honour of all those people working and wishing they were in school, here is a time-wasting list of 10 great songs, novels and films that evoke those heady days of learning. In making my incomprehensive, highly subjective selections, I decided to avoid works that fall into subgenres like inspirational-teacher movies (Dead Poets Society and The Paper Chase), frat-house sex romps (Revenge of the Nerds and Old School), campus novels dealing mostly with faculty (Kingsley Amis’s Lucky Jim and Francine Prose’s Blue Angel) — they all merit complete lists unto themselves.

Carrie, Stephen King (book)

King’s first novel, adapted into a movie starring Sissy Spacek, is about a teenage girl who uses her telekinetic powers to strike back at the classmates who’ve mistreated her. Even after a film like Elephant, which was inspired by real-life high-school shootings like Columbine, Carrie still remains a potent high-school revenge fantasy.

From left, Judd Nelson, Emilio Estevez, Ally Sheedy, Molly Ringwald and Anthony Michael Hall get detention in the John Hughes film The Breakfast Club. (Universal Studios)

The Breakfast Club (film)

John Hughes’ 1985 comedy about a group of kids in weekend detention anatomized the range of misfits roaming high-school halls and created a template for teen movies.

Another Brick in the Wall, Part II , Pink Floyd (song)

This song, from Pink Floyd’s concept album The Wall, is probably the anthem of every disaffected high-school student (“We don’t need no education”). Note: This is the only time a children’s choir has ever been used effectively in a rock song.

Dazed and Confused (film)

Richard Linklater’s mastery of dorm-room philosophy shines in this story that follows the last day of high school for a group of Texas students in 1976. It also introduced the group Foghat (Slowride) to another grateful generation.

Principal’s Office, Young MC (song)

This bubblegum rapper — less obnoxious than MC Hammer, less talented than the Fresh Prince — is better known for his one big hit, Bust a Move. This pleasant ditty captures an unlucky day in the life of a high-school student.

Rushmore (film)

The pre-psychedelic Brit rock, the droll zingers and the Byzantine hipster-kitsch of Wes Anderson’s films were still fresh and affecting when he made this story about a playwriting boy (Jason Schwartzman) who loves everything about his school, except the classes.

Never Let Me Go , Kazuo Ishiguro (book)

Ishiguro’s eerie dystopian tale is narrated by Kathy H., who speaks elliptically about her time in a boarding school. When the reader learns the real reason she’s at this institution, “school” becomes a place that’s both sinister and sad.

From left, Lindsay Lohan, Amanda Seyfried, Rachel McAdams and Lacey Chabert get nasty in the 2004 film Mean Girls. (Paramount Pictures)

Mean Girls (film)

A young(er) Lindsay Lohan stars as Kady, a girl who has moved back to the U.S. from Africa, where she was home-schooled by her zoologist parents. Kady wryly compares the habits of teenage girls to the rules of the jungles, before succumbing to her own animal instincts.

Prep, Curtis Sittenfield (book)

This bestselling first novel, about an Indiana girl who goes to a tony boarding school near Boston, helped revitalize the boarding-school subgenre, thanks to a female point-of-view and abundant humour.

Campus, by Vampire Weekend (song)

To my ears, there’s something about the clean-sounding guitar work and dweeby-clever lyrics about Oxford commas of this NYC indie band that reminds me of the more eclectic, unpolished college rock of ’80s bands like Camper Van Beethoven and the Feelies. This song seems to be about someone running into a “cruel professor” on campus and trying to conceal their crush.

Kevin Chong is a writer based in Vancouver.