Newsletter 153: On Woody Allen in the Year 2019

I’ve decided to start putting some of the best newsletter essays here on Medium, so more people can read them. You’re still better off just subscribing. This one’s from April 2019, when I finally had my Woody Allen reckoning. Seems apt at this particular moment.

The summer after high school graduation is one of the more memorable periods in anyone’s life, the final stretch where you are a child before you head out to the world to discover who you really are. (Or at least whom will you pretend to be for four years.) Some kids travel; some have one final high school fling; some just sit at home and stare at the wall until September comes and they get to leave.

For me, it was the summer of 1993. My best friend Tim Grierson had learned in April that he had been accepted to the film school at the University of Southern California; I was going to the University of Illinois 45 miles up I-57. I’d be an entirely different, much worse person today had Tim not been my best friend in high school. In high school, in many ways, you are your friends; there were a ton of shitheads at Mattoon High School I could have been best friends with, and it was just my good fortune that I found the thoughtful kid who was as obsessed with movies and Kurt Cobain and the Cardinals as I was. (These people aren’t easy to come across in rural IIllinois.) I’d hung out with Grierson every day…