5 Insane Celebrity Jack-o'-Lantern Stencils (Tested)

5 Sylvester Stallone

I started my adventure by choosing a modest 20-pounder from my local pumpkin store, one with a significantly flatter side to make it a bit easier. I laid it out on my trash-bag table and eyed it as Michelangelo did the marble that would become David, in that I suddenly had the urge to cut a tiny dick out of it.

Since I forgot to buy an actual pumpkin-carving kit, I improvised with some nearby kitchen tools, and also a wine corker, because there was no way this was happening without drinking.

As I cut the lid, I thought to myself, "Pumpkin insides didn't look like this when I was 8." It resembled the scene from Aliens where they discover the Xenomorph cocoon. I'm now convinced that, in the intervening years since my childhood, thanks to Monsanto, pumpkins have become taxonomically classified as animals.

After washing my hands of pumpkin guts, I got to work. First, I placed a printout of what is supposedly Sylvester Stallone's flat face over the round pumpkin, which according to my schooling should be a violation of geometry. Then, I painstakingly poked holes through the outline and cut. I'm pleasantly surprised the end result was at least somewhat recognizable.

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4 Buckminster Fuller

For my second attempt, I tackled a stencil of the late, great inventor Buckminster Fuller, because if there's anything that kids love on Halloween, it's neo-futurist geodesic dome enthusiasts who died 31 years ago. For Buck, I ventured into the "specialty pumpkin" section, which was just filled with gourds with acne.

I grabbed a small, stemless, white one, as the guy apparently had a forehead that you could project a movie onto. I'm not bragging, but the template claimed it was a "Level 3 Advanced" carve, and the final product was actually pretty good, maybe even better than Sly. I also felt bad about picking a stemless pumpkin, so I accessorized him with a gourd hat, because if you're not going to take October seriously, go live in another month.

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3 Luciano Pavarotti

With Stallone and Buck done, I put them on my porch so that my neighbors knew how much I love Philadelphia and/or cars shaped like giant pickles. But my joy was short-lived: it took mere days for Fuller's head to collapse under his own genius and for Sly's mug to oxidize into a silent scream. I was forced to euthanize them both via garbage chute.

My next pumpkin tribute to scare the kids silly was the opera singer Luciano Pavarotti, who has been dead for seven spooky years. I have no idea why the hell you would want him on your front porch unless you were the conductor of the Turin Symphony Orchestra, but All Hallow's Eve was rocketing toward us like an out-of-control steamroller. There was no time for questions. I'm proud to say I got the basic shape, but the more intricate cuts eluded me. The only way I could do Pavarotti's hairline was to just scrape his forehead with a steak knife, just like barbers do in real life.

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2 Spanky From The Little Rascals

If you're the kind of Cracked reader who remembers the Great Depression in vivid detail, chances are you're acquainted with The Little Rascals and its lovable cast of grime-smeared orphans and racial stereotypes. My next pumpkin to win over trick-or-treating millennials would be gang leader Spanky, whose cherubic countenance was made for a pumpkin.

I began by picking (what I thought was) the most Spanky-shaped pumpkin possible. Unfortunately, I didn't really measure beforehand, so the stencil could comfortably fit in only one horrifying direction.

I shortly ran into trouble with the shading. Going along the open cuts was easy enough, but I don't understand what tool you could possibly use for those tiny outlines, as my pumpkin had what appeared to be mammalian veins. Also, the shaved portions were not nearly thin enough to allow candlelight through, so I hid it in the corner of my porch, away from mortal eyes.

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This carve was the one I dreaded most. The cuts were absolutely ridiculous, and the pattern looked like a plague victim rather than an amiable sasquatch who reaps in way more 1980s nostalgia than he actually deserves. My pumpkin's four-inch-thick walls stymied any attempts to carve an outline. When forks and corkscrews barely made a dent, I actually began drawing freehand. Remember how I mentioned I'm not an artist?

As this pumpkin was genetically spliced with concrete and shadows, I didn't even bothering with a candle and just covered the outside with what I assume were wacky catchphrases from the movie. I have never seen the movie.

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Chris is never going to carve a pumpkin ever again. Follow his other antics over at Laffington.com or tell him how awesome these are on Twitter.

For another DIY scary story, check out 7 Gross Foods Your Grandparents Ate (That We Taste Tested).