Don’t you just love a good old fashioned Halloween costume contest? How about one held outside on a busy city street? How about one held in the year 2000? Well…

Yep, here’s a 12-minute video of a deliriously of-its-time Halloween costume contest held on Milwaukee’s Water Street 23 years ago! It’s filled with basic costumes (witches and skeletons), creative costumes (Indiana Jones w/boulder), elaborate costumes (a Borg from Star Trek), duo costumes (Hans and Franz), and extremely early-’00s costumes (Mark Chmura w/teenage girl). And while nothing jumps out as wildly offensive as a winning Aunt Jemima costume the following year, there are plenty of costumes that absolutely wouldn’t/shouldn’t fly today (Mark Chmura w/teenage girl).

Watch the video on YouTube HERE.

Here’s a partial list of the costumes seen in the video. Pocahontas and Warren from There’s Something About Mary are big no-no’s, too.

• Stormtrooper

• Yip Yips from Sesame Street

• Mark Chmura w/teenage girl

• Indiana Jones w/boulder

• A Borg

• Members of Blue Man Group

• Cuban cigar w/Zippo lighter

• Zorro

• Chewbacca

• Darth Maul

• Warren from There’s Something About Mary

• Pocahontas

• Glinda from The Wizard of Oz

• Mona Lisa

• Cruella de Vil w/Dalmatian

• Boba Fett

• Racing Sausages

• Kenny from South Park

• Beetlejuice and Lydia Deetz

• Mr. and Mrs. Potato Head

• Catwoman

• Hans and Franz

• Pinhead

And yes, this video previously made an appearance on our 66 Days of Halloween countdown. We’ve fallen a little behind on the countdown—mostly due to the site crashing when we try to edit the ever-growing article—but we promise to get back on track soon! Here’s a Hans and Franz sketch!

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About The Author

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Co-Founder and Editor

Matt Wild weighs between 140 and 145 pounds. He lives on Milwaukee's east side.