My Bloody Valentine/Silent Night, Deadly Night - Timeline

The timeline either goes 1, 4, 2, 5, 3 or 1, 4, 5, 2, 3... just to make things even more complicated!
i take 1,4,5,2,3 well i'd take 1, 4, 2, 5, 3 for a different reas and for the sake of our convenience not to deal with a film taking place simultaneously. As well, thanks to news paper in 5 we know the film can take place the earliest in 1991 but thanks to age of our characters it also could be in 1992.

as for Part 2, personally I rather ignore the ages he's talking about but won't ignore the 5 year time jump, he is crazy he could convince himself that he's 18 instead of 21 XD but loosing step father? idk i think he would not make up that part. but that's my opinion
 
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So... according to this short (starring Eric Freeman as Ricky Caldwell), there was a film starring Eric Freeman as Ricky Chapman in-universe about the events of the second film, which means...

In-universe films series:
Silent Night, Deadly Night 3: Better Watch Out! (Made before 1989)
Silent Night, Deadly Night (Made in 1991)
Silent Night, Deadly Night 4: Initiation (Made before 1992)
Silent Night, Deadly Night: Part 2 (Made after 1991)

The in-universe third film hilariously came out before it even happened.
 
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Silent Night, Deadly Night #1-4 only really references the first film, but it isn't irreconcilable with the sequels so that's okay. Ricky had a family after 3, was arrested again, escaped, then reverted back to his birth name. Honestly, this series has a surprisingly strong continuity all things considered. Good stuff. I'm really confident in these placements being 100% accurate too.
 

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