Yandere Toons x Reader: An Anthology of Headcanons and Scenarios

Oogie Boogie (Platonic & Romantic Headcanons)

TW: Mentions of Kidnapping, Implied Death & Stalking, Emotional Manipulation, Toxic Mindsets.

A.N. - I memorized every line of his song. Also, I was just thinking of doing headcanons for Jack a few days ago to welcome October.

Platonic:

Oogie is a fan of all things dramatic. The other people in his friend's life are no more of a threat than a loose stitch, but his refusal to stay out of the spotlight for long drives him to order his henchmen to abduct these perceived interlopers and dump them into his torture chamber. Once there, he regurgitates their every flaw and laughable quality, tearing them down emotionally before tossing them into his vat of stew.

No matter how much terror is caused or how many nightmares are induced, Oogie scarcely views the situation as more than a delightful game of roulette to toy with and indulge in whenever he gets the urge to destabilize his friend's life. The incentive for these mean-spirited attacks is often as simple as rolling a more favourable dice value than him. He assures them that the games are merely for recreation, but his persistence in achieving a winning streak implies that the stakes are much higher than a lost afternoon.

The fear that his behaviour inflicts is a source of pride for Oogie. He jokes about cooking the kinder inhabitants of Halloween Town into his stew to pressure his friend to end relationships abruptly and without an obvious motive, which gradually strains their reputation until they are as despised as he is. Acts of rebellion are met with taunts, for Oogie is confident in Lock, Shock and Barrel's ability to retrieve them if they were to escape.

Romantic:

Oogie is an avid cheater who has little to no integrity when it comes to his gambling practices, hopelessly rigging every game and machine in his lair. The Boogie Man challenges his partner to rounds of poker where the reward for beating him is freedom, a promise on which he would never deliver unless Jack was present and melting his bugs until he capitulated. In the unlikely event that they win, Oogie denies it by either inventing rules that nullify their victory or, if they show an insistence on leaving, threatening them with his Snake and Spider Stew.

The residents of Halloween Town live in fear of the name Oogie Boogie, limiting his partner's options for help to a lucky rescue by Sally and personal intervention from Jack. Word of their captivity reaches the Pumpkin King via gossip, and Lock, Shock and Barrel are ordered to act as spies who track and torment anyone suspected of scheming to free them. While Oogie recognizes that Jack is a genuine threat, he will feign uncertainty and cowardice at the mention of the skeleton to lull his partner into a false sense of hope.

Due to his banishment and a healthy fear of Jack's wrath, Oogie spends most of his time in his underground casino. He relies on his henchmen to supply information about his partner's daily activities, adding the names of those who bully or are too comfortable with them for his liking to his hit list. All his deception and time spent fretting over his status as an outcast has shortened his temper and eroded his patience, so Oogie devises a plan to trap them in his lair.