Why it Matters: Songs that shaped the music industry and our modern world


Credit: Best Classic Bands

Ruby Voge

Breakup songs: From “You’re So Vain” to “All Too Well”

For almost seven decades, the break-up song has remained one of the most ubiquitous and consistent staples of 20th and 21st century pop music. Sometimes they’re angry, meant to be screamed in the car and shouted in the shower. Think: “You Oughta Know” by Alanis Morrisette. Other times, they’re solemn and regretful, mourning a relationship that was gone too soon or simply happened at the wrong time. Think: “River” by Joni Mitchell. They may even be bittersweet, reminiscing on past love while also acknowledging that the break-up was meant to be. Think: “Ivy” by Frank Ocean. Regardless of the song’s tone, we keep coming back for more to because we love to experience the emotional catharsis of the songwriter through their music. Breakup songs specifically allow us to reminisce upon our own past experiences and reflect on the good, the bad, and the ugly of the ghosts of lovers past. However, it’s not only the emotional release that we are addicted to, but also the mystery. Many of the most famous break-up songs contain subtle, or not so subtle, references to real life spouses, partners, and flings. And, because we’re all a little bit nosy, we enjoy piecing together the hints and clues to try to sleuth out

Carly Simon’s 1972 folk-rock classic, “You’re So Vain,” was the ultimate pre-Twitter subtweet. Since its release, critics and fans have pondered the identity of its cocky, self-obsessed subject, all while being entranced by its distinctive guitar introduction, clever lyrics, and Simon’s strong vocals. The true genius of the song is in the simplicity of its chorus: “You’re so vain/You probably think this song is about you/You’re so vain/ I bet you think this song is about you.” No one in their right mind would dare claim that they were who Simon was singing about, thus allowing her to remain silently cryptic on the issue. So, for over forty years, members of the press speculated that the song referred to an array of famous musical men, including James Taylor, Cat Stevens, David Bowie, and David Cassidy, which Simon denied. When, in 2015, Simon finally confirmed that the second verse was written about Warren Beatty, an infamous womanizer, no one was particularly surprised. However, she has remained hushed on the topic of the song’s other two verses, leaving plenty of room for continued theorizing about trips to Saratoga and apricot scarves.

Fifty years later, we are still doing the same thing, only with new songs, new artists, new exes, and different colored scarves — they’re red this time, not apricot. Ever since her fast and early rise to fame at the mere age of 16, Taylor Swift’s love life has been examined and scrutinized under the magnifying glass of the modern media’s hamster wheel-esque gossip cycle. The re-release of her 2012 album, Red, provided avid fans with not only 9 new “From the Vault,” but a 10-minute version of her masterpiece, “All Too Well,” along with a short film, starring Sadie Sink and Dylan O’Brian. Rife with new details and piercing word choice, the release of Red (Taylor’s Version) has ignited a whole new era of internet discourse surrounding Swift’s relationship and subsequent breakup with Jake Gyllenhaal. However, Taylor’s prowess in this area did not begin, nor end, with “All Too Well”. In fact, she has been penning spectacular breakup tunes since the release of her self-titled album in 2006. From the wistful “Tim McGraw” and satisfyingly angry “Picture to Burn” to the beautifully painful “Back to December” and the emotionally raw “Dear John,” Swift’s songs provide both the relatable feelings and intriguing mystery necessary for a perfect heartbreak pop hit.

Check out the playlist below for some of my favorite breakup songs, in chronological order: