Yom Kippur is the traditional Jewish day of atonement but my day of penance for the past twenty-five years has come a few weeks earlier. It’s gone by several different names and has moved locations and undergone a lot of upheaval but is currently called Expo Chicago. It’s just an art fair but it never fails to stir up all sorts of conflicted feelings about the commercial and social side of the business I’ve devoted most of my life to. Every year I say I won’t go back but September comes and I can’t stay away.

Navy Pier has been the fair’s home for most of its nearly forty years of operation. Having to walk the length of that tourist-infested food court/tchotchke mall to get to the show will test even the sunshiniest souls. The $20 admission doesn’t help anyone’s mood either. This year, for the first time, there’s also a $2.50 amusement tax which isn’t noted on any signage and comes as more salt on the wound.

My usual strategy is to walk all the aisles quickly, then go back to linger with whatever caught my eye. I’m pretty inured to the gallerinas, avant-garde eyewear, and uncomfortable outfits of the attendees. I also don’t bother with much video, photography, installation, or sculpture. I’m sure there’s worthy work in those mediums but when faced with some hundred exhibitions crammed into one you have to pick and choose. I only really care about drawing and painting so that’s what I look for.

This time I was struck by how much of the stuff looked like wrapping paper or an outer shell, as if what I was looking at was hiding something more inside. Trouble is that there isn’t anything inside; visual art is all on the surface or else it’s not really visual. Of course paintings can have meanings beyond a first impression but it all has to stem from what is visible. If you have to read or have what you’re looking at explained to you the piece of art has failed.

I always end up wondering whether I’d hate the whole thing less if I was part of it. But because I rarely have a good time at my own openings I kinda doubt it. Still, it would be nice to get a little acknowledgement in my field. I saw a few people I knew. Some I’d gone to school with who have done well in this environment. I don’t envy them because I know I can’t do what they had to do to get where they are. Year in, year out I look for Robert De Niro paintings. He was the actor’s father and is mostly forgotten today but is one of my favorites. I only saw one this time around and it wasn’t a great one, but it was comforting to see it, kind of like encountering an old friend.

Like every year, after leaving the fair I feel instant relief. Even the tourists zombie-lurching from Build-A-Bear to Bubba Gump’s Shrimp Company seem to burst with life. I always wonder why I wasted $20 when I could’ve just sat on a bench and watched this parade of humanity and not feel like such a failure.

Maybe in twenty years or whatever, when I’m gone, if they still have art fairs, something of mine will be on one of these temporary walls, and maybe, if I’m lucky, someone will take the time to seek it out. But by then it won’t be my concern. All I know is I’m definitely skipping it next year.

—Seventeen years ago I wandered into the Empty Bottle from work at Bite next door and saw a schlubby guy in an ugly, multi-patterned button-down shirt asleep on the couch. A couple hours later, that same guy got up on stage with an acoustic guitar and played a bunch of his beautiful songs to the couple dozen of us in the audience. After awhile he even took requests. He said he’d play any Husker Du song that he wrote and he did. A few times he stopped mid-song to add sarcastic asides like, “Insert gratuitous guitar solo here.” It was a show I remember as much for how haunted and ravaged he seemed as for the music. RIP Grant Hart.

—RIP Harry Dean Stanton. Thank you for Paris, Texas and so many others.