DBD Killer Timeline
Since I have nothing better to do, I decided to put together a timeline for when each Killer's story took place. This took, honestly not that much time, but some of it is obviously questionable (Namely the Spirit). And since a lot of these stories could have taken place during a large time period, obviously some Killers are in the wrong spot, but this is the best I could do.
Obviously, Anna the Huntress is first. The devs have confirmed this personally. But, since I did a bit of research, I'll give the evidence anyway. During the last paragraph of her backstory, it is mentioned that German soldiers are "on the march to attack the collapsing Russian Empire." Notice it says RUSSIAN rather than SOVIET. The German invasion of Russia occurred in 1914 (although I am currently unable to find that information now. Stupid Google search not liking me). She was taken by the Entity afterwards.
Sally the Nurse appears to either be around the time of WWI or WWII, judging by her outfit. If she is from WWI, it would make her the second oldest Killer. But if she is from WWII, then Kenneth/Jeffrey begins before her. But his is a bit complicated, and will span a few other Killers' backstories.
Either way, since two decades pass during Sally's backstory, and I don't think they would change the Nurse dress code simply because of money restrictions, her story seems to end around (based on her being from WWI) the 1930's or (based on her being from WWII) the 1950's-1960's. She kills everyone in the asylum and presumably crashes the ambulance, killing everyone in it, before getting the Entity treatment
As I said, Kenneth's backstory takes place over a long time. We actually have an exact year for it's beginning. "Kenneth Chase was born in 1932 by a difficult labour, which his mother wouldn't survive." Doesn't get any more crystal clear. The last year mentioned is 1954, which also coincides with when I believe Evan the Trapper's backstory to occur.
Given that Evan and his father very clearly don't allow a union, they are either relatively new or really picking up speed. And given their extreme measures, I would believe unions to be nearing their peak in all honesty (also, since unions were around since 1881, they can't be a new thing, since Anna's story occurs well after that, and remember, she is the first). Obviously, Evan blows people up, and the Entity gets him.
While all of this is going on, the Cold War is in full swing and the CIA is likely getting Soviet spies. And who was hired by the CIA for interrogation? Herman Carter. The Doctor. Mr. Lag Attack himself (seriously, my computer is amazing but I lag every time against and as him). Everyone knows how that goes down. He ends up killing everyone at Léry's and the Entity gets him.
Kenneth, now going by the name of Jeffrey, goes on for another decade, bringing us to the 1960's once again. I honestly can't tell how much time passes, but eventually, he rides his carriage into the Entity's realm. I'd say this takes place around the 1970's, but again, there are no real markers to tell us.
I'm just going to put Lisa the Hag here, in the 1970's, but she is one of the really annoying ones. There are NO markers to tell us when her story takes place, but I'm placing her here since, from what I can tell, the 1970's brought a resurgence of witch culture, which Lisa has plenty of. Even her WIP name was the Witch. But again, her story could have taken place at any time.
Hillbilly and Rin the Spirit are in the same boat. I would place Hillbilly sometime between the 1970's and 1980's, which is when the Poulan 306a was in production. Why is this important. Well... once again, there are no significant markers for Hillbilly, but I would assume he and Leatherface use the same chainsaw. If someone can actually tell me what model of chainsaw Hillbilly (who is UNNAMED officially, but the wiki calls him Max Jr. [Edit - as DocOctober brought up, he is named Max Thompson Jr. in an official artbook, although his lore makes no mention of it for some reason) uses, then do so. I'm not a chainsaw expert.
Rin is the MOST complicated. Her story has no years, no significant events to talk about, and none of her add-ons help. I thought that her baseball cap would be something, but sport caps were invented in 1849, which is WAY before Anna. Then something caught my eye. "That evening, Rin came home from work. She'd stayed late to entertain customers that lingered at the restaurant. As she parked her bike in the shed, she heard her mother's scream the house."
As she parked her bike (I have no clue how to increase the font size here, so bolding will do). What's the relevance of this? Bikes weren't introduced to Japan until 1971! I can't place her exactly, but I can tell her story takes place after this. We will have to deal with this.
Of course, that was no help. As GamingZebra pointed out, the Japanese military used bikes in their invasion of China in WWII. So Rin is a serious issue that needs addressing. She is probably pretty modern, as PigNRun says, since she was working at a young age and her father was a salary person, but we might have to wait for something more concrete with her (got it, as I'll explain below).
If you count the licensed Killers as canon (which I do), then Leatherface arrived in 1974. My evidence is plain and simple. Texas Chainsaw Massacre was released in this year. Although, I have personally never seen the movie, so this could be different and I would have no idea.
Same goes for Michael Myers. Halloween was released in 1978, but I can actually find the timeline there. The movie starts in 1963, then 15 years later, Michael goes on his killing spree. 1963 + 15 equals 1978, so that adds up. But I am not putting Freddy here, because, like it or not, the in game Freddy is from the remake.
Taking a slight break from the licensed Killers, we have Philip the Wraith. I put him in the 1990's as this was when the Russian mob appears to have been the most active. Why am I talking about the Russian mob? Philip's boss is named Azarov. Azarov is a Russian surname. He disposes of people using a car crusher. To me, that seems like a VERY mob-like way to get rid of someone. On a side note, why DID the Entity take Philip. Is it the same as Rin, where the Entity picked up on his anger or something?
The Legion would be in the same boat as Rin, maybe even worse, if it wasn't for Susie. Normally, I wouldn't consider cosmetics to be canon, but the devs seem to have out of their way to give us a year with Susie that I'll consider her two cosmetics canon. But just hers, not Joey's (if you look VERY closely at the Legion picture, both teaser and selection, you can see Joey's mask there). Her sweater on both of them give us the year 1996. They kill the janitor and get grabbed by the Entity (unfortunately, as I've figured out in the past, they are NOT grabbed with Jeff, which is a wasted opportunity and a half).
EDIT: As of January 15, I have actually found something for Rin. It is far simpler than I had originally believed, which is probably why I missed it in all honesty. The university she goes to, Takamatsu, wasn't established until 1996. Meaning this is the EARLIEST year she can be from, and I'd wager that she's probably later than that. But that's as far as I can go with her.
The final two are easy. Amanda's story includes her death from Saw III. "She failed the test and took a bullet as a consequence. Bleeding out on the tiled floor, darkness engulfed Amanda's vision, accompanied by a sound like creaking wood." With Saw III being released in 2006, it feels to me like that is when her story takes place.
And once again, Freddy Krueger is from the 2010 remake of A Nightmare on Elm Street, likely because they couldn't get the rights to Robert Englund's character, so they settled with Jackie Earle Haley instead (I know people are going to hate me for this, but I like this version of Freddy a little bit more, just without the sexual predator part. Englund's version got a bit too comical, and I like the burn effects).
That took way too long to type. If there are any glaring issues, please tell me. I'll see what I can do to fix them.