Boo

It's been a tough year in our business and I've endeavored to find new things to keep the group morale up. We had a barbecue one balmy summer day and we try to do the odd sundry event to encourage collective cohesiveness. We're on the precipice of the month of October so naturally, Halloween looms. We need a costume contest.

There was a time when we naturally dressed up in costume for work on Halloween. Being a product of San Francisco, many of the men I knew needed little encouragement to don their best drag and parade through the streets, through the aisles at work and through the many bars alight with post work celebration on glorious Halloween. Over the years, this tradition tapered off and less and less people did dress up for work on this unique holiday. Well, the HR people always dressed up in the hopes of fueling a dying tradition and sadly they were usually dressed as clowns.

Today as Hollaback and I drove home from work I announced my intent in reviving the Halloween spirit in the Connecticut office. I was sure this enticement would stir some of the clearly obvious spirits in the office to new creative heights but I also had to accept the fact that some of the more cautious types would resort to more safe pedestrian wear (including a facilities manager who sat close to my office--given my pathological loathing of clowns, this could be dicey).

Hollaback rose to the occasion. She agreed to trot out her bat costume, an ingenious bit of outfitting made of black garments, headpiece and a few dismantled umbrellas. Excellent. I began to imagine what costume I should attempt. I mean, I had to remember my target audience. Here, I was completely flummoxed.

We brainstormed and Hollaback suggested the late Anna Nicole Smith. That seemed tough. Enacting someone in the nth stages of rigor mortis seemed challenging and let's be honest--it would be completely lost with this audience. Britney Spears at the VMAs had HR Nightmare written all over it. Finally Hollaback suggested a pre-rehab Amy Winehouse (above). I'm all over the idea despite the fact that 80% of the staff in Connecticut won't know who I'm supposed to be (in fact I suspect only Hollaback, me, the cool dude from the mailroom and the IT guy from the Bronx will actually "get it").

So I'm kind of at a loss. What's a culturally courant costume that doesn't fall into sugary sweet territory that will convey some sly humor to a group of 40-something workers in Connecticut? If anyone has a suggestion, I'm all ears.