Anastasia Reddie Dimitri: Richie Anastasia: Eddie Vladimir: Ben Rasputin: Pennywise
Basically Eddie doesn't remember any thing before the age of 13 and when he turns 18 he wants to know where he came from. He meets Richie and Ben who are in search of the lost prince Edward kraspbak for an award by themother. They find Eddie and teach him how to be a prince and don't mention the reward.
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My Own Private Idaho Bichie Scott Favor: Bill Mikey Waters: Richie Carmella: Beverly
Bill and Richie are hustlers. Bill is on the streets to rebel against his wealthy dad and Richie never knew any other way to make money with is narcolepsy. As Richie fails to remember where he came from, him and bill embark on a journey to find Richie's mother.
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Note: Mikey is cannonly gay and in live with Scott but it's one sided
Toy Soldiers Stozier Billy Tepper: Richie Joey Trotta: Stan A boarding school gets taken over by terrorist and the only way the trouble makers can get the student body safe. Richie is the "bad boy" leader of the group with resentment towards authority and Stan is the aspiring artist with resentment towards his dad.
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Note: Billy and Joey are not cannonly gay in toy Soldiers but I still like the concept.
500 days of Summer Benverly Tom: Ben Summer: Beverly Ben is head over heels for Beverly, but she is free spirited and not ready for commitment. Ben tries to pinpoint what went wrong in their relationship and how to fix it.
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Monk Stenbrough Adrian Monk: Stan Natalie: Bill Julie: Georgie An OCD ridden Stan needs an assistant to help him perform his everyday job as detective. Bill gets that job in order to take care of his younger brother Georgie, but being an assistant to a mentally unstable man is harder than it looks.
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Note: throughout monk Natalie and Adrian stay friends but I like this concept sooo...
The Office Stanlon Jim: Mike Pam: Stan Mike works as a salesman for a paper company, but most of his time revolves around flirting with the receptionist Stan.
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BONUS ELF: Buddy!richie Jovie!eddie
Parks and Recreation: April!eddie Andy!richie Leslie!bill Ben!stan
Stranger things: Eleven!eddie Mike!Richie or Eleven!Bev Mike!Bill or Ben
