“And What Are You Supposed To Be?” The Halloween Costumes That Haunt Me

I was the most neurotic child you’d ever meet. I’ve had anxiety for as long as I can remember. It was particularly manifested each and every October. There was a decision to be made of significant measure. The stress would get to me. It drove me to the bottle – mostly Squeeze-its and Sunny D. Not that purple stuff. I had to consider functionality, practicality, and most importantly originality. What footprint do I want to leave? Do I want to be the hero or the villain? To be alive or amongst the dead? Would I be someone people truly remember throughout history or just a topical flash in the cultural pan? This decision would determine social standing amongst my peers for months, and if not executed carefully it may determine the course of my youth. Intense, isn’t it? This is the childhood crossroads of choosing a Halloween costume.

What’s astonishing about putting all of this weight into my decision? I repeatedly botched it. If Halloween costumes were judged like candy, I was a Mounds bar. And just like a Mounds bar, nobody liked me. Even when I thought, “Mike, you are totally crushing it this year,” I look back now and find a litany of my choices to be hilariously awful. Even if the idea was adequate, the execution failed (a minor precursor to the story of my life). I always made odd choices for a kid (for instance, morning cereal of choice: Cracklin’ Oat Bran; first celebrity crush: Bonnie Hunt; musical preference: Meat Loaf). Halloween was no exception. Allow me to outline some of my poorer costume selections:


Fat Ninja (1992)

You cannot go wrong being a Ninja. I consider being a Ninja now. There’s only one way being a Ninja goes wrong: A massive cold front comes in bringing freezing rain, snow and bitterly cold wind on Halloween night. No mother is letting their child out in those conditions wearing only party store polyester. Therefore I had to add layers of thick clothing, a winter coat, gloves and a scarf to my armor. I was as nimble and elusive as a fire truck. My all-black Japanese mercenary attire was pulled over all of this insulation truly making me…a fat ninja. I essentially was better off going as a char-burnt Stay Puft Marshmallow Man.

Dracula (1993)

This is as typical a Halloween costume there is, but my fake fangs led to one thing: saliva everywhere. I was insistent on staying in character and leaving the plastic novelty teeth in my mouth at all times. This resulted in parading around my neighbors Halloween party spitting and drooling on everyone and everything. I was a great Dracula, if Dracula were to be shot with a horse tranquilizer and heavily sedated.

Phantom of the Opera (1994)

You read that right. I was indeed the darkly romantic, whimsical title character of Andrew Lloyd Webber’s Tony award-winning Broadway play…at the age of 9. My mom had given me the idea and yes, I loved it. We went to see the play as a family a few years before and outside of some boring musical acts (it is a musical? I’ve been had!), there was nothing about Phantom I didn’t like – a cool mask, ominous horror, a falling chandelier – I was sold. So for the 4th Grade Halloween parade I put on my black jeans (one of my many pairs), a white dress shirt, the black cape, and the iconic white half-face mask. I went to school and needless to say…the teachers loved it. My fellow students didn’t have a clue. During the school parade I heard them shout, “Two Face!” and “Confused Batman!” And in dark, fanciful form as only the Phantom could, I turned to them with my cape drawn over my forearm and proclaimed, “No, no. I’m Phantom. Phantom of the Opera.” It was at that moment I wish the mask covered my entire face. Sure, it bought me some ridicule and name calling because as we all know kids can be dicks, but my attitude about that costume now? I’d say it was ahead of its time, but you probably want to avoid any costumes synonymous with Broadway musicals when you’re 9 years old and walking in a Halloween parade between an X-Men and a Power Ranger.

Robber (1996)

My idea of a thief at that time was less Danny Ocean and more Tom & Jerry. I wore black wind pants, because an assailant always wants to be heard swooshing around the target’s house sounding like an early 90’s mom chaperoning a field trip. I put on a plain black Turtleneck. Nothing says “member of the criminal underworld” like a form fitting turtleneck by OshKosh B’Gosh. After trying to put pantyhose over my face and realizing it was both itchy and disturbing, I sponge painted a fake light black beard and donned a hamburglar mask and black knit cap. I thought I looked coarsely intimidating, but my parents thought I was just the cutest little cat burglar.

Laurel & Hardy (1998)

You would think I learned my lesson about being somewhat obscure adult characters as a child for Halloween with the Phantom of the Opera fail, but I was at it again, this time with my twin brother. We had grown up going over to our Grandparents and watching their old movies. Our favorite was Laurel & Hardy’s Way Out West from 1937. So we thought, why not do this for Halloween? Why we asked that rhetorically I’ll never know. I now have a dozen reasons why we shouldn’t have done that for Halloween. Only one neighbor recognized who we were and she was 74 years old. The next best guess came from parents who called us Charlie Chaplin. Among the many troubles of 12 year olds trying to be Laurel & Hardy (we may have been the only ones ever) is Laurel was a slender man and Hardy was obese with a petite old fashioned mustache, but my brother and I were both just the chubby kid kind of fat. We also didn’t sell our roles enough so each house opened its door to what only looked like a couple of plump little Hitler’s. This was a time of boy bands, MTV, and Dawson’s Creek. Who would have thought being pre-World War II silent movie actors wouldn’t be a hit amongst the tweens? Everyone. Everyone would have thought that.

Bob Slydell (2003)

I looked forward to this for 4 years in High School. Every Halloween the seniors got to dress up for school. It was finally our time. I was coerced into joining my friends in our attempt to be the character ensemble from Mike Judge’s cult classic Office Space. The problem here was that I joined the group late, so the good characters were all taken. I was only left with the choice to be one of the Bob’s. The other Bob dropped out which should have been my time to wave the white flag, but I stayed on to portray Bob Slydell of the two Bob’s. As critical and hilarious as Bob Slydell was to the movie (“I gotta say, I am a Michael Bolton fan”), being him for Halloween was worthless and confusing. Impersonating this Bob required me to wear suspenders, a white short-sleeve dress shirt, slacks, and mat down my hair with gel in an attempt to mimic his hairline. I also had to sport a small trimmed mustache. Once again I was more likened to Hitler. I’m going out on a limb here, but I’d venture to say the majority of people never want to be likened to Hitler. I managed to do it twice in the span of a few years. Sure I had the office look, but when you don’t actually have the facial features or haircut of John C. McGinley’s Bob Slydell and you walk around school with your backpack on in slacks and a short sleeve dress shirt, and without the rest of the cast, you end up looking like Hitler, the Travelling Bible Salesman.


I’ve had my fair share of flops. Halloween costume stress is now a thing of the past. These days if I ever have to dress up for a party I respond like an adult by drinking until I’m not self-conscious about it. This is no matter. I’ve totally got this year locked down. It’s between Senate Majority leader Harry Reid, Carl Winslow, Dame Judi Dench, or America’s favorite lesbian superhero He-Man. If I really want to put a scare into all the women and children I could go as the corpse of Chris Berman, but we’re subject to that freak show every Sunday on ESPN.

One day I’ll have children and they’ll be faced with making Halloween costume decisions. I pray they won’t have their father’s neurosis, but that they choose wisely to avoid ridicule and embarrassment. And if they ask their dear old Dad for ideas I’ll be ready with my list of Broadway icons, Hitler look-alikes, depression-era silent film actors, and the fat version of otherwise acceptable concepts.

Happy Halloween everybody.

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2 thoughts on ““And What Are You Supposed To Be?” The Halloween Costumes That Haunt Me

  1. Omg! This was great, Mike! I, too, felt your pain when it came to Halloween costumes. I would start stressing about what my four kids would wear in early August. (I couldn’t sew and back then the store bought costumes were not like they are today!). Your article brought back lots of fun and funny memories. Enjoy Friday!!!!👻


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