First off, I watched Fate/Zero first before getting onto the other routes of Fate/stay night. Sue me if you will.
If you haven't even touched the Fate series yet....what are you doing. As to what order to watch it in:
Fate/stay night (2006)
Fate/stay night: Unlimited Blade Works (The 2014 TV anime, not the Studio Deen movie that came out in 2010)
Fate/stay night: Heaven's Feel (coming out 2017)
Fate/kaleid liner Prisma☆Illya (If you want. I personally found it a fun "what if" story, as it has more Illya XD)
As for watching the 2006 Studio Deen adaptation, that one's kind of up to personal preference, depending on whether you would actually want to sit through a playthrough of the game on YouTube.
But after seeing an entire Let's Play of the Fate route on YouTube, I do have to agree with a lot of VN players when they say that the visual novel is the best way to get into the Fate series. As an anime only watcher, this can be a bit of a gripe seeing as the ufotable adaptations require you to have some knowledge of the Fate franchise. Granted though, I got into it by watching Fate/Zero and then UBW and then checked out the Let's Plays of the VN on YouTube and Fate/Zero is arguably the best way to get into the series as of late. But I'll be talking mainly about the anime adaptations, as that was my intro to the Fate series to begin with.
Seriously, whenever I try to download the game its like I have to download and do a ton of other shit before I get it to work and quiet frankly, I don't wanna destroy my laptop.
With that said: Holy shit.
I had no idea what to expect from this series, seeing as it was based off a visual novel from 2004 with a lot of world building. I mean, an adaptation from a manga is hard enough. How the hell were they going to pull this off in a 26 episode anime?
Lemme put it this way: Studio Deen failed miserably. Ufotable succeeded beyond expectations.
Let me clarify before I go any further: I don't outright hate the original anime. It is massively flawed but I have seen a lot of poor adaptations to call this one pure crap.
So Studio Deen adapted the Fate route of Fate/stay night in 2006. While I liked the pair up of Shiro and Saber, Studio Deen majorly fucked up the damn route by adding elements of (and in the process, spoiling) the other two routes, Unlimited Blade Works and Heaven's Feel, and I watched this route after finishing ufotable's adaptation of the Unlimited Blade Works route. I understand that as an anime adaptation, they were trying to merge the three routes as a singular, definitive adaptation but honestly, the three routes are completely different stories under the same setting for the most part so combining them really seems like the worst direction you can take for an adaptation.
Arkada once said this about the Fate series: "There is never going to be a perfect adaptation for the Fate games." In fact, the ufotable adaptations are the closest thing we're ever going to get as just anime watchers. Reason being, there's just so much material to pack into a 26 episode anime. And in ufotable's adaptations, there's at least three - four episodes that are double the length. In Fate/stay night: Unlimited Blade Works, there was three of this caliber. In Fate/Zero, the first episode was literally the length of a goddamn Once Upon a Time episode.
Even with that in mind, it was kind of a downer to be honest because while Rin Tosaka is a good character and match up for Shiro in the UBW route, I was really looking forward to seeing Saber and Shiro slowly fall in love with each other....without all of the sexist/misogynist writing and having Shiro actually doing something like in UBW and in addition, not act like an idiot. Its granted that I would think this seeing as UBW is my favorite route but at the same time, I am rather fond at the thought of Shiro and Saber as....well, something more.
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