Masquerade

My mission for Halloween 2007 was simple. Since I've moved to Chicago and learned to cope with the rigors of waking up in the morning consistently for the first time in six months, I've been playing things close to the vest. I've yet to go to work with a hangover, and more often than not I've been getting an appropriate amount of sleep each night. Clearly, this had to stop, and what night was better for ending this trend than this? With that in mind, I headed to the Metro for what turned out to be an ass-kicking show from Art Brut and The Hold Steady. Both bands brought it hard in the costume department, although Elvis jumpsuits are not always flattering. The Hold Steady also announced that the show was being recorded for a live album/DVD, which should be outstanding as the show was epic.

As I was walking to the Metro, I thought I would swing by and check out the big gay Halloween parade careening up Halsted. This year marked the 11th annual North Halsted Parade, and I applaud any event that combines a costume contest for children with the shenanigans of Boystown. Where else can you combine the cuteness of this......with the subtlety of this...
In case you're wondering, the collective pictured above dubbed themselves "The Cockettes." They were pretty tame compared with some of the more adventurous parade-goers.

But try as they might, Santa's not so little helpers did not win me over for best costume of the evening. That honor belonged to another attendee. I don't think I've ever been jealous of a kindergarten-aged lad, let alone jealous of their wardrobe, but I was in complete and unadulterated envy of this tyke's get up:
What kid this age has any basis to know who Conan O'Brien even is? I guarantee when I was his age I wasn't begging my mom to let me dress up as Tom Snyder for trick-or-treating. Kudos to you kid. You've set the bar high for Halloween 2008. Hope you weren't planning on dressing as a Cockette. That costume is taken.