The Simpsons: 10 Most Disturbing Episodes
1. Bart Sells His Soul
Bart Sells His Soul will always rank as one of the best episodes that this show has ever produced. It's dark, hilarious, thought-provoking but most of all, disturbing.
The episode begins with a large-scale prank from Bart at church and culminates with him and Milhouse being forced to clean an organ together. After discussing the existence of souls, Milhouse offers to purchase Bart's since he doesn't believe in them. After he agrees, his life soon takes a downward tumble as he is struck with bad luck, cannot laugh, and is plagued by some hauntingly dark dreams.
The episode masterfully blends tones as it shows the depths of anxiety and regrets that Bart experiences through his actions in the real world and the events depicted in his nightmares. The combination of his desperation and sadness put tonnes of pressure on the young boy and make the events of the outing tough to sit through.
Thankfully things do end well for him, but the episode leads you down a rabbit-hole of anxiety as you fear not only for his sanity but his possible damnation.