This feature was originally published in November 2013.

nos·tal·gia noun [no-stal-juh, -jee-uh, nuh-] : pleasure and sadness that is caused by remembering something from the past and wishing that you could experience it again.

Rob Sheffield once compared music to a time machine. Songs remind us of times in our lives, and familiar sounds trigger familiar images in our heads. Subconsciously, the music attaches itself to the context in which it was experienced most intensely, and by listening to it, we are taken back to that moment. Music and nostalgia are intertwined in this way.

Yet nostalgia is a universal human emotion, so we decided to flip the scenario. Instead of listing the songs we found nostalgic, what about compiling a list of songs that are nostalgic? Many songwriters have made a career off tales of troubled pasts and old girlfriends, but then there are those certain songs that epitomize the idea of nostalgia. Most of them are frankly very sad, as the past is always dotted with could’ves, should’ves, and would’ves, which are easy to dwell upon.

Some, however, reflect with resignation, accepting that one can’t change the things that’ve already happened. The 21 songs here depict 21 distinct ways of coping with, embracing, and analyzing the past. View this list less as a “best of” and more as a psychological breakdown of nostalgia in pop music.

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