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An Exhausted Parent’s Guide to the 13 Spookiest Moments on Sesame Street

It's Count von Count season

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Sesame Street Scariest Moments
Illustration by Steven Fiche

    Halloween brings chaos. I don’t know about you, but we were late to buying costumes, early on eating candy, and the squirrels have ripped the faces off our jack-o’-lanterns. That attack has made them much more upsetting to look at — for me. Our toddler loves them, and cries when we don’t let him bring the rotting guts inside.

    Young children enjoy a good scare as much as adults do, and every Halloween it is a parent’s sacred duty to give them the willies without also giving them nightmares. Sesame Street has now invested over 50 years in that pursuit, and this list collects 13 of their most creepy, unsettling, and all around spooktacular sketches.

    The videos that follow showcase plenty of classic puppetry and a few horror parodies, but Sesame Street is much more than that. I’ve also included a few of the most disquieting cartoons, plus an episode that got yanked from circulation after a deluge of angry letters. And of course, there’s plenty of The Count von Count, who mellowed in recent years but used to have a lot more bite.

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    Check out all the tricks and treats below. If you’d like, you can also revisit the Exhausted Parent’s Guide to the Top 10 Musical Guests on Sesame Street.


    13. Don’t Die in The Crossing Zone (1990)

    “At the end of every street, there’s a special place,” Gordon (Roscoe Orman) says in a Rod Sterling monotone. “A place where horns honk and cars whiz by. At the stoplight up ahead, you have entered ‘The Crossing Zone.’

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    This Twilight Zone parody is built around a boy, Jonathan Wilson, who eventually “asks one of my grownup friends to help me,” across the street. Gordon can be Sesame Street‘s most stern character, and he looks the camera dead in the eye as he intones, “Never cross the street alone. Ever.” Combine this message with skin-tingling music, and you might just scare kids into staying on the sidewalk.

    12. These Jaws Are Brought to You by the Letter J (1995)

    Something lurks beneath the chlorinated waters of this community pool and no amount of shark repellent will keep it away. The “Underwater Letters” series of 1995 is an homage to director Steven Spielberg and the music of John Williams. As strings rise up the scale in a minor key, we see watery images of kids and something getting closer and closer. Suddenly, the letter of the day would rear out of the water. Instead of being devoured, the swimmers would cheer.

    The full series ran through the letters E, F, K, N, R, S, W, X, and Y with the same formula, and if you were a kid in 1995, you saw them all. But even if you know what’s coming — even with images of smiling children on a bright sunny day — that theme song combined with those camera angles can’t help but feel like doom.

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