I haven't really seen anyone point this out yet and I can't stop thinking about it so I'm writing it out.
When the Loser gang leaves Derry after all is said and done the first time they all forget. It's assumed that it's directly Pennywises fault. They all become somewhat happy successful people. And yet every single one of them have something that makes their happy life a living hell. It's basically a deal with the devil. Every loser has to deal with something.
Bev marries a man only to realize he's the exact copy of her father. He beats her and forces her to have sex with him. And yet she's a successful fashion designer.
Eddie marries Myra who is exactly like his mother. She's anxious and worried all the time constantly looking out for Eddie. She won't stop assuming the worst. Eddie calms her down and makes her anxiety his responsibility. And yet he works a job that is perfect for him: risk analyst.
Ben loses all the weight that caused him so much torment. He even keeps it off. No longer the fat kid. But he realizes it never ment anything because what he wanted was Bev. And yet he becomes an architect.
Stan marries an amazing woman that supports and loves him. Against the wishes of both their families and they still flourish. He gets a job that pays six figures. But they are never able to make a larger family. They try for years and yet no children. They go to doctors who tell them both of them are perfectly fine and able to have children. Yet Stanley knows on a level that isn't possible that it is because of him.
Richie becomes a comedian. Always down for a good joke with people that always laugh. He finally had people that held onto everything he said. No one ignored him or thought his jokes were bad. He literally make it his job. But in the process he was always a little aware of what he lost. His discontent came with having no actual friends. He was never able to place the feeling but him forgetting was his own hell. He didn't need anything other than isolation to be tormented.
Bill becomes the author he always was destined to be. He makes books that delves into the supernatural. Perhaps he always had some gut feeling just out of reach that everything was real. He suppresses his stutter and finds a girl that looks like a Bev. He gained all these things while still knowing he was missing something. Georgie was always and forever in the back of his mind.
Mike was an exception. He didn't leave. He was the one who had to give up everything in order to ring the metaphorical bell. He is just a librarian. He doesn't have everything the others did because he didn't leave. In the book it's insinuated he was half aware. Not quite remembering but eventually woken by the memory of Pennywise and the Turtle. He suffered majority of that time knowing that they were gone.
Leaving Derry gave them everything they every thought they wanted while keeping whatever it actually was they desired away.
(take everything I've said with a grain of salt because I've only watched both movie versions and haven't finished the book yet. It's just a thought. All three versions make it clear they all are unhappy.)



















