At 10 minutes to midnight on February 29, 2012, I ran to my computer and compiled a list of nine songs I thought would sound good together. I began with Bob Marley & The Wailers’ “Concrete Jungle” from Babylon by Bus. That rush spawned a project: every month I would make a new iTunes mix. I wouldn’t start picking songs until the 1st and at the end of month the playlists were fixed in stone. In between, anything goes.

Flipping through my 29 completed monthly playlists I see evolution in my musical taste: more hip hop (hi, The Roots), the emergence of Sonic Youth as a favorite band, more Elvis Costello, more jazz (starting with Coltrane and Miles, then broadening to other artists like Nicholas Payton). There’s still plenty of blues-rock, but it’s a little less prevalent. Some months turn out better than others. April through June of ’14 are strong, and my Octobers are great. The Novembers don’t measure up.

My brother Tyler is responsible for all of this. He loved making iTunes mixes. He worked in a hurry, sometimes playing a new song just once or twice before he slotted it into a mix. He also liked to repeat artists in his mixes, and I think he felt it gave his lists more character. I don’t do that, and I treat random songs from compilations as key spices. But that’s the fun: the rules are arbitrary, and by imposing artificial constraints on yourself, you create something revealing.

Now to get started on July.

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