Halloween is a great concept, but it often suffers from the curse of heightened expectations. There’s a lot of pressure on Halloween, not the least of which is coming up with a sweet costume. It’s especially difficult when the people you roll with fancy themselves artists, because artists are better at making things than you are. As a writer, I’m really good at describing things, but not so skilled at making them. If Halloween only existed on paper, I might stand a good chance at winning first prize in the costume contest, but not so much in the real world where you’re expected to actually assemble the things you see in your head.
I’ve only experienced a handful of really good Halloweens in my adult life. My first Halloween in New York, back in 1998, was a good one. The evening began at my friend Matt’s friend Matthew’s place in the East Village. That isn’t a typo, Matt’s friend was named Matthew. I didn’t know anyone, but there were a couple of cute girls there. I don’t remember my costume. I’m sure it was something that was supposed to be conceptual, because at the time I thought the best thing you could be on Halloween was a punchline. The year before I had dressed like a hobo in a shirt that said “She didn’t look 16.” I was a poor excuse. It was a poor costume.
When we got to Matthew’s place, everyone was watching a Gallagher comedy concert that Matthew had on tape. This was before DVDs. I looked at his tape collection and he had a lot of Gallagher tapes. I think he liked Gallagher ironically, but it was that kind of ironically that was only there to make it okay for him to really like Gallagher. Like how I pretend to think Lady Gaga is awesome because I really think Lady Gaga is pretty awesome. It’s a thin line. The interesting thing is, if you asked Matthew if he liked Gallagher ironically, he would say, “no, I really like Gallagher,” because if you admit that you only like something ironically, then you’re just trying too hard. So he pretended to like Gallagher for real to cover up the fact that he liked Gallagher ironically but underneath it all, he really liked Gallagher for real. Phew. Being cool is hard.