Another school year is upon us. So many songs that have become engrained in culture have been inspired by the artists’ experiences during their school days and the paths they forged for the future. Education-based reflections of the struggles, triumphs, hopes, dreams and relationships that either lasted — or never panned out the way we’d hope — can be a great unifier for groundbreaking artists and music fans alike.
From rising alternative pop act glaive on the prom experience to Regina Song’s reflections on high school romance to Chance the Rapper recalling a school suspension, De La Soul’s classic lovestruck school anthem and Columbia University’s own Vampire Weekend’s tales on “Campus,” we’ve put together your soundtrack for the bus ride, carpool, dorm room or just for some real-life inspiration.
LISTEN TO THE SONGS FOR SCHOOL DAZE PLAYLIST ON SOUNDCLOUD
glaive, “the prom”
The alternative pop vocalist and producer came up on SoundCloud, posting tracks during the pandemic. His latest album is May 2026’s ‘God Save The Three.’
Regina Song, “high school boy”
Regina Song is a Singaporean vocalist and songwriter who crafts tender pop jams about youthful love, life and heartache, as heard on June 2026’s ‘everland.’
Slyy Stone, “freshman 15”
Currently working on his debut album, Slyy Stone blends internet rap, electronic pop and indie on his hooky tracks.
Daniel Arison, “High School”
Miami-based artist Daniel Arison released his debut EP, ‘Nostalgia Really Hurts,’ in 2025.
Brielle Kaga, “Love As Good As Mine”
Brielle Kaga has been writing original songs since she was a young teenager, and those stories of school days are folded into her lyrics. Her latest is March 2026’s ‘Sober Up.’
Chance the Rapper, “14,400 Minutes”
On the cover of “10 Day,” his debut mixtape, Chicago’s Chance the Rapper looked every bit the schoolboy in his ball cap and his varsity jacket. But the opening track breaks down all the minutes he spent – 10 days’ worth – out of school during a suspension.
Fetty Wap, “Wake Up”
“Can I get five more minutes?” Fetty pleads on this 2016 reminiscence. It’s the rallying cry of anyone who’s ever wanted to roll over and hit the snooze button, instead of rallying for yet another humdrum day of school.
3 Titans (feat. Menahan Street Band), “Life of a Scholar”
Looking for some inspiration as you get back to the books? Jordan Plaines, Kahlil Jackson, and Dallas Ifill — the three young scholars — were 11 years old when they cut this single for Brooklyn’s Daptone Records.
De La Soul, “Jenifa Taught Me (Derwin’s Revenge)”
De La’s long-overdue release from bureaucratic limbo means a new generation gets to experience the joys of one of hip-hop’s all-time freshest groups. “She was in my English class,” explains the late Trugoy the Dove (RIP), and the boys take the tale from there.
Taylor Swift, “High School”
The pop behemoth reflects on her school days on this yearning track from her album ‘The Tortured Poets Department.’
Asher Roth, “I Love College”
“I want to go to college for the rest of my life,” Asher Roth declares on his 2009 debut single, which doubles as an ode to the best parts of the quintessential college experience.
Leaders of the New School, “Case of the PTA”
Proteges of Public Enemy, this Long Island group ran the gamut of a typical school day, from “Homeroom” to “Afterschool,” on their 1991 debut, “A Future Without a Past.”
Dead Prez, “They School”
For the great duo Dead Prez, the usual school learning could never take the place of being self-taught: “I was reading Malcolm / I changed my name in ‘89, cleaning parts of my brain.”
Boogie Down Productions, “You Must Learn”
Famously, KRS-One has always been about gaining that knowledge. “When one doesn’t know about the other one’s culture / Ignorance swoops down like a vulture,” he raps on this classic from 1989.
Monie Love, “Monie in the Middle”
It’s a classic tale of schooldays crushing: Monie has her eye on this one boy in class, but some other “knucklehead” won’t leave her alone. Bring back that New Jack Swing!
Juicy J, “Scholarship” (feat. A$AP Rocky)
“Say you need some extra cash to pay for college with / And it just so happens I got a lot of it,” raps Memphis’ own Juicy J on the opening of “Scholarship.”
Young M.C., “Principal’s Office”
Young M.C. ruled the roost with “Bust a Move.” One track before that all-time banger on his 1989 debut album was “Principal’s Office,” which details an unfortunate day at school.
Big Daddy Kane, “Rap Summary (Lean on Me)”
The legendary emcee samples the great Bill Withers on his second album, 1989’s “It’s a Big Daddy Thing,” spitting, “Wanna go to college, or wanna be garbage?”
Vampire Weekend, “Campus”
Has there ever been a band quite as college-oriented as Vampire Weekend? They met at Columbia University and sang about the “Ladies of Cambridge.” They even wrote a song about the debate over the “Oxford Comma.” To use or not to use?
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