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VOICE OVER: Emily Brayton WRITTEN BY: Cassondra Feltus
These dark moments make "Over the Garden Wall" a perfect Halloween watch. Welcome to MsMojo, and today we're counting down our picks for the creepiest, most tragic, and most disturbing scenes in the autumnal cult classic. Our countdown includes Greg's tree transformation, the soul in the lantern, the Highwayman song, and more!

#10: The Highwayman Song “Songs of the Dark Lantern”

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On a dark and rainy night, Wirt, Greg, and Beatrice find a secluded tavern but, before they enter, they see someone watching them from the window. Already weary and on edge, they’re met with chatty, slightly off patrons in an atmosphere that can only be described as unsettling. The aforementioned window-watcher, aka the Highwayman, forcefully steals the show when he sings this jazzy but mournful tune, vaguely describing his penchant for theft…and perhaps murder. We’re captivated by his fluid movements, reminiscent of Cab Calloway’s rotoscoped dancing in “Minnie the Moocher.” The whole performance is instantly eerie, and honestly, it’s a perfect villain song.

#9: Meeting the Pumpkin People of Pottsfield “Hard Times at the Huskin’ Bee”

Like everyone Wirt, Greg, and Beatrice meet on their journey, the residents of Pottsfield are Strange with a capital S. The trio stumbles upon their harvest celebration and Wirt assumes it’s a cult of people donning pumpkins. Their towering leader, Enoch, doles out a lenient punishment to the trespassers, which at first seems to be literally digging their own graves. Needless to say, they’re pretty freaked out when they unearth two skeletons who start dancing with their fellow deceased comrades. That’s right, underneath their gourdy costumes, everyone is a skeleton. Despite the morbid setup, the Pottsfield-ers are a laid back community all about farming and partying in the afterlife. What the Pumpkin Girl said to Wirt makes a lot more sense now…

#8: Adelaide & the Bluebird Curse “Lullaby in Frogland”

Beatrice promises to take her new acquaintances to see Adelaide of the Pasture, the Good Woman of the Woods, who can supposedly help them get back home. But after growing fond of the boys, Beatrice tries to call off the deal she made with Adelaide – two young servants in exchange for undoing the curse on her and her family. The witch possesses the bird-shaped scissors needed to cut off their wings, a horrific method to return the bluebirds to their human forms. The finale shows that the family’s humanity has been restored, which is good…but we can’t help but think of them going through the cruel process. At least they’re able to joke about it.

#7: Auntie Whispers’ House of Doom “The Ringing of the Bell”

When Wirt and Greg meet a young woman named Lorna, they find out she’s essentially a prisoner of Auntie Whispers, a hideous witch who eats turtles and immediately gives off villain vibes. The brothers, and the audience, are led to believe Auntie Whispers is just another Wicked Stepmother… with a mind-controlling bell. However, it turns out that she’s trying to keep Lorna occupied to stave off the evil spirit that possesses her and its need to devour humans. Lorna’s sudden transformation into a ravenous demon is truly frightening. Thankfully, Wirt casts out the spirit. The ending where Auntie Whispers gets emotional sort of implies that she let Lorna stay possessed so that she wouldn’t leave... Now that’s dark.

#6: Greg Saves Wirt from the Beast “Babes in the Wood”

By episode 8, Wirt is done. He’s convinced they’ll never get home and just gives up, dismissively passing the role of leader onto Greg. The latter takes his new responsibility seriously and thinks about a plan while his brother sleeps. He dreams that he saves a place called Cloud City and is granted a wish by their queen, using it to take Wirt’s place as the Beast’s next victim. We watch as Greg willingly goes off with the Beast, believing he’s saving his brother and will get them home in the end. The endlessly optimistic boy doesn’t seem to realize the danger he’s in and we’re left with a sinking sense of dread.

#5: The Soul in the Lantern “The Unknown”

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From the first moment we meet the Woodsman, he’s carrying the Dark Lantern. He believes it holds his daughter’s soul and it’s crucial that it remains lit to keep her soul alive. But this turns out to be a lie from the Beast who manipulated the Woodsman into being the lantern bearer. This isn’t discovered until Wirt is given the same choice and he quickly realizes that the Beast must be so adamant about keeping the lantern lit for selfish purposes. The truth is a crushing blow to the distressed father who’s been working hard to protect the lantern for years. After he extinguishes the Beast, the Woodsman returns home and reunites with his daughter. He was the one lost in the woods all that time.

#4: Wirt & Greg Almost Drown “Into the Unknown” & “The Unknown”

The penultimate episode of “Over the Garden Wall” takes us back to the events preceding Wirt and Greg’s arrival into the Unknown. While fleeing from the police for being out in the cemetery, the brothers narrowly avoid being hit by an oncoming train, fall down a steep hill, and land in a lake. In the finale, Wirt comes-to in the water and pulls out Greg and their frog, and they’re taken to the hospital. The fate of children is always a grim subject and seeing the brothers almost drown suggests they were unconscious underwater and at great risk of dying the entire time. This supports the theories that the Unknown is actually the place in limbo between life and the afterlife.

#3: The Truth About Edelwood Trees “The Unknown”

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As we’ve discussed, the Beast lied to the Woodsman because he needed someone to guard his lifeforce. But that’s not the only thing he lied about. The Beast seeks out lost children who work themselves to exhaustion trying to find their way home and turns them into Edelwood trees. The Woodsman would cut down said Edelwood trees to then create the black oil needed to fuel the lantern. When he finds out that the many trees he’s dispatched over the years are young souls, he is horrified and visibly distraught, as anyone would be.

#2: Greg’s Tree Transformation “The Unknown”

After reconnecting with Beatrice, Wirt finally finds Greg but what he sees is his sickly brother mid-transformation into an Edelwood tree. We saw Greg earlier when the Beast tried to get the Woodsman to use him for oil. But watching Wirt realize the very real possibility that his little brother could die, and Greg seemingly accepting this fate, is a heart-wrenching moment. Wirt admits that everything he tried to blame on his little brother was actually his fault, and finally accepts responsibility for his actions. Wirt’s crying, we’re crying – and it doesn’t help that a melancholic rendition of “Potatoes and Molasses” plays during the scene. Before we unveil our top pick, here are a few honorable mentions. The Struggling School House, “Schooltown Follies” Miss Langtree’s Heartache & Her Father’s Financial Woes Add a Touch of Sadness to an Otherwise Lighthearted Episode Beast Dog Attack, “The Old Grist Mill” The Temporarily Feral Canine Turned Out to Be Beatrice’s Poor Pup Under the Influence of Evil The Lonely Tea Baron, “Mad Love” Quincy Endicott Is Really Going Through It. He Also Alludes to Acquiring His Wealth Through Questionable Methods Adelaide’s Death, “Lullaby in Frogland” A Melting Witch Isn’t Anything New but Seeing It Happen So Suddenly Was Unexpected & Quite Disturbing

#1: Beast Reveal “The Unknown”

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For ten episodes, the Beast can be heard taunting the Woodsman and trying to lure in Wirt and Greg. All we can see of him is a looming silhouette with branch-like antlers and glowing eyes. That image is scary enough but what he actually looks like is next-level nightmare fuel. Before the Woodsman blows out the lantern flame, there’s a blink-and-you’ll-miss-it spotlight reveal of the Beast’s full form. The trypophobia-triggering tree body is made up of anguish-faced Edelwood trees who we just learned were once children. While he was effectively terrifying enveloped in darkness, the Beast is shockingly grotesque in the light. Which of these moments made you shudder? Let us know in the comments below.

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