The Art of Mixtape by Sun Tzu
When your enemy is downstream you must put Train songs in the water.
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Like everyone, I came of age during an in-between period. My particular generation had a few in-betweens: VHS switching to DVDs, the changing of Regan-era Republicanism to the miserable centrism of “Third Way” Democrats, and whatever you call the period between the “End of History” and what History did next. The creation of digital music libraries and the phasing out of physical CDs makes up the crux of the in-between period that this newsletter covers. During this period, say 2003-2008, the culture as a whole lost all sight of what makes a good playlist. Unfettered from the restraints of physical media, playlist makers became unmoored losing the best of part of a playlist – the time constraint. With the ability to burn multiple album’s worth of MP3 files on to a CD-R, and eventually the ability to share and send them digitally, playlists have metastasized, growing exponentially. I submit that the maximum length for a playlist – what I in middle school used to call a “mix” – should be 90 minutes, and that the best length is around 30-45 minutes.
The scourge of overlong playlists has not passed me by unfortunately. At this moment any person near me could hear song 167 of a 198-song playlist coming from my headphones. “Burn It” by Joshua Ray Walker if the title interests you. The playlist is named, quite cleverly, “Starred.” This playlist is too long. I created it in 2011. If I wanted to send it to someone it would take that person 11 hours and 21 minutes to listen to the whole thing. And this playlist pales in comparison to my “Summer Jams” playlist which has ballooned to 362 songs compromising a length of 21 hours and 18 minutes. I originally made this playlist in 2014 as a place to keep songs that didn’t go on the Starred playlist, because that “was getting too long.” It did not work.
Playlist-smithing did not always have such a crisis of identity. Back in the early aughts CD-Rs hard-capped at 90 minutes of music if you wanted it to play on a CD-player. That meant one could include about 20-23 songs at most. Picking 20-23 songs, especially when someone could use that CD to judge your coolness level? Probably one of the hardest things I’ve ever done in my life. Being forced within a limit forces the playlist-wright to make a choice. Similar to how haikus work. Rather than just throwing in 8 songs that all do the same thing in slightly different ways, a limit requires picking the perfect song as to not squander the limited digital space.
Short playlists have other benefits besides their rigid structure. A good playlist gets better from repeated listens. Unheard connections between songs on a well-designed playlist become apparent on multiple listens. Cool little musical flourishes reveal themselves. If you hear a song from your playlist in a different context you get disappointed when the next song isn’t from the playlist. Getting any of this from a 36-hour “Good Songs” playlist is impossible. With a 30-minute playlist, you can listen to it multiple times, fully ingesting the music, deciding whether the person who sent you the playlist wanted you to notice just how many of the songs contained lyrics about love, or heartbreak. Listener and Creator both benefit.
In the spirit of this newsletter I’ve created a 30-minute playlist. Every song sounds the same. You’re welcome.
Oh and here’s a funny video.