Ahhh Halloween the holiest of holidays, celebrating the demon spirits in all of us as we vandalize, binge and lament the true horror upon us, the holiday season. But before any of the “fun stuff” first thing’s first – finding a costume … a hilarious, ironic, original walking piece of art work that will put you on the hot list of whatever party/parties/galas you attend ... don't be the guy still dressed as The Joker (Rest In Peace Heath). Here are the top 5 Halloween costumes that won't embarrass you.

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October 27, 2010

#5 Mad Men’s Ken Cosgrove

Look, Mad Men costumes are now Mad Dated costumes – the conventional ones anyway. If you’re a hot busty redhead you’ve already been Joan once or twice, and dressing as Don?! Please … costume-wise that dude is a cut rate Dick Tracy.  However, if you come to a party as the milquetoast Ken Cosgrove, everyone will applaud your ironic flair. Items needed for costume: blonde hair, boring suit and a copy of The Atlantic Monthly (a magazine that published his short story) Difficulty: milquetoast

#4 Lt. James Rupert Rhodes AKA War Machine (the Terrance Howard version)

Super heroes are classic Halloween costume fodder … yawwwwn. Why do you want to go as Iron Man?! Are you 8? Are you without originality?! Go as the man behind the man behind the iron man, Lt. James Rupert Jones! PLUS you get to go in black face (depending on your own race), which is ALWAYS a party starter. Just don’t go as the Don Cheadle version, while we all thought it was better casting, it just wasn’t. Items needed for costume: war machine suit, or dress-blues and a solid Terrance Howard impression. Difficulty: Don Cheadle

#3 Chilean Miner (any of them)

It’s topical-ish, and generic enough as a costume that you can throw this one together, and hey, if the outfit was comfortable enough to last 66 days, I think you can swing it for an evening. Added bonus if you can get a whole group of dudes to come also dressed as Chilean Miners. Items needed for costume: Chilean flag, hardhat, wrap around shades to help you see in the dark tunnel (I guess?). Difficulty: subterranean 

#2 The Twitter Bird

Everyone knows this now iconic bird (although who knows what kind of bird it is really) and it will certainly garner you a few conversations about twitter thereby getting you more followers (follow @pauldanke). If you REALLY want to shine on the judges, bring a fat friend to pose as the Twitter Fail Whale – everyone will get a chuckle. Items you will need for costume: a bird costume, a blue one, you should also have a twitter account. Difficulty: for the birds

#1 Cigar Guy

The best Halloween costume is obscure enough where everyone else isn’t in the same get-up but popular enough where everyone recognizes it immediately – enter The Tiger Woods scene-stealer Cigar Guy. For whatever reason, a miracle happened recently where Tiger hit a ball directly into a camera, and that ended up being the least interesting part of the photo. A modern day Bigfoot, Cigar Guy appears in the photo, while there are still discussions as to his authenticity, obviously he did something right. This look will steal any Halloween costume contest (unless it’s judged by stupid girls). Items needed for costume: Mario mustache, Rick Ross sized cigar, a red wig WITH ponytail and an ugly ass jacket.

Difficulty: Sssssssmokin'