I hope everyone is having a good Christmas, or at least an okay Friday!
I've been working all week and visiting friends in the evening, so I haven't had a chance to do more than half of the next rewactch. And I probably won't until next week or so. BUT, to tide you over, I figured I'd do another one of these things...
Also, FYI: I go by chronological time in these things - meaning that I account for the years that the show skips.
1979 - Dean's first Christmas! He's nearly one and it's ADORABLE. Aww, happy times.
1983 - Sam's first Christmas! He's just over 7 months old and Dean is nearly 5... but, uh, it's a pretty crappy Christmas. Mary has been dead for nearly two months and everything is horrible.
1985 - Somewhere during this month, the Milton family got their Christmas miracle when they had Anna, even though they were supposed to be infertile. They'll have a good many years before that bites them in the ass though, so happy times!
1990 - It's Adam Milligan's first Christmas! He's just shy of 3 months old and he's super adorable. He celebrates it with his single mom, and both are completely unaware of the horrible fate he inherited from his absent unknown father.
1991 - Sam and Dean spent Christmas together in Broken Bow, Nebraska, while John is on a hunt. John doesn't make it back for Christmas day, but Dean steals Sam some presents to try to make up for it. In return, Sam gives Dean an amulet he had originally intended to give to John. Sam learns about hunting and what his father has REALLY been up to for his entire life.
1993 - It's Kevin Tran's firs Christmas! Awww, so ADORABLE. He's only a few week's old.
2002 - It's Sam and Dean's first Christmas apart. They are probably both pretty depressed about it.
2003 - Sam tries to keep his friend Brady on the straight and narrow, after he returns from Thanksgiving with a bizarre change in personality. Or, perhaps "Brady" went home for Christmas too - in which case Sam is probably just worried about him.
2004 - It's Sam and Jessica's first/only Christmas as a couple.
2005 - It's Sam and Dean's first Christmas after being reunited! John isn't with them, but I'm sure they're in a good mood after just recently clearing Sam's friend Zach of murder charges.
2006 - The boys spend Christmas in and around Peoria, IL. This time, John isn't with the boys because he's dead, which, I'm sure, puts a bit of a damper on the celebrating. On top of that, things might still be a little tense between Sam and Dean, given that Dean has come clean about John's last words and they are both now worried about Sam's future. Not only that, but Sam's friend Ava has disappeared and her fiance has been murdered.
2007 - The boys spend Christmas in Ypsilanti, Michigan. Sam was reluctant to celebrate, but then came around to the idea for Dean's sake. The Christmas is bittersweet, as, unless Sam can save him, it will be Dean's last Christmas.
2008 - While ordinarily, the boys might have been celebrating the capture of Alastair, Dean's torturer in Hell, this Christmas probably sucks, because it happen just three days after Pamela's untimely death at the hands of Alastair's demon minions.
2009 - I'm not entirely sure where the boys are this Christmas - they could be feeling pretty good after successfully saving Chuck and Becky from a haunted Supernatural Convention, or they could be dealing with the aftermath of their failed attack on Lucifer and Ellen and Jo's tragic deaths, or they could have just escaped a psych ward after saving Dad's old friend Martin from a wraith. Personally, I hpe it's the first option, as that would make the the best Christmas of the three.
2010 - Dean has his first Christmas with Lisa and Ben. I'm sure their company is much needed, as Dean is no doubt missing Sam tremendously. Sam's body, meanwhile, is off hunting with their newly resurrected grandfather. Sam's soul is in Lucifer's cage and I doubt he knows what day it is - he probably just knows torture and pain.
2011 - It's hard to pinpoint this Christmas, but it could possibly occure during the week that Sam is in a coma after Dean gets Death to restore his soul. Or, if could be that spending Christmas with a soulless Sam was what drove Dean to seek Death's help in the first place.
2012 - Sam and Dean spend this Christmas together. Sam is having difficulty with the wall in his mind crumbling, Dean's alcoholism and depression are acting up. Cas is believed to be dead, but is actually living as an amensiac named Emmanuel, who just got married to the woman who found him wandering around naked. Hopefully, the boys are with Bobby, because this is actually their last chance to celebrate Christmas with their surrogate father.
2013 - Sam spends Christmas at a motel in Kermit, Texas, with a dog. He has just started seeing an angry veternarian named Amelia. I'm sure it's a really sucky Christmas for both of them, because it's Amelia's first Christmas without her dead husband and Sam's first Christmas without Dean. And they're probably both just getting hammered and having depressing sex. Dean and Cas, meanwhile, are killing things in Purgatory. Kevin thinks Sam is dead and is hiding out someplace, on the run from Crowley's demons.
2014 - Sam and Dean celebrate Christmas together again! Yay! Cas is also back from purgatory! Yay! Kevin and Mrs Tran are safely on Garth's houseboat! Yay! There are evil things afoot, of course, but they aren't afoot RIGHT NOW.
2015 - Sam and Dean have solved the mystery of where Garth disappeared to, but that's just about the only thing that's nice about this Christmas. Kevin is dead. Dean has the Mark of Cain. Sam is super duper pissed off still. So.. yeah, my guess is that this is the most awkward Christmas ever.
2016 - This is probably another tense Christmas, but for other reasons. It's clear that the Mark is causing Dean to go into indescriminate killing rages and that's never a good thing. Cas, meanwhile, has both saved his vessel's daughter, Claire, and managed to piss her off even more... so, that sucks for him.
2017 - ... we'll have to stay tuned to find out!