The Saddest Breakup Songs Of All Time

Illustrated by Sydney Hass.
The Ronettes had it all wrong. The best part of breaking up is not the making up. That rarely happens, and when it does, it often leads to more breaking up.
No, the real pleasure in having your soul shredded by another human being comes in the days, weeks, months, or maybe even years of wallowing that follow. It’s a chance to wear pajama bottoms past noon and indulge in some serious self-reflection — the type that makes you a stronger, better person. This journey into the self can be scary, but luckily, generations of musicians have written songs to soundtrack the plunge.
What follows are the saddest (and therefore finest) breakup songs of all time. On this list you’ll find no TSwizz “We’re Never Ever Getting Back Together" (too empowering) or Alanis Morissette “You Oughta Know” (too angry). These songs are plain and simple, rip-your-heart-out sad. Play ‘em just loud enough to drown out the sobbing.