When I first went to see Paprika in theaters, one thing that caught my attention was the voices. At first, I could not pinpoint them. Who is the main character? I know I’ve heard her voice before… And then it hit me: Hayashibara Megumi, that most prolific of 90s voice actors (who’s still doing work today and has recently written her own book), was the voice behind Paprika. Then another voice struck me. THAT FAT GUY IS AMURO RAY! I felt the desire to jump out of my seat and shout, “AHA!” but decided against it. Unfortunately for me though, I was not accompanied to the theater by any friends who were particularly into anime, so I could not share my discoveries at the time.
There are anime fans who have watched just as much if not more than I have, who are unable to pick up on a character being voiced by an actor from their favorite series, but there are also anime fans who have watched far less than me who are able to pick up on the subtle nuances of a voice and determine, despite any sort of wild differences in the voices used for the two characters, that the same actor plays these roles. And they’re not even always seiyuu otaku!
What is it that makes some people more able to recognize voice actors than others? I’m not applying this solely to Japanese seiyuu, but rather voice actors in general from Frank Welker to Kamiya Akira. I don’t consider myself to have a keen sense of hearing, so I can’t say I’m particularly tuned to any difficult-to-perceive aspects of voices, but when I do notice a recognizable voice, it generally has to do with something that one role has in common with another, even if those roles vary wildly. Of course, I don’t always get it right, and there are times when a voice hits me but I just cannot pinpoint it. I don’t know, I unfortunately do not have the proper vocabulary to explain it.
Perhaps someone with greater knowledge of voices and audio could explain better.
OGIUE MANIAX 
I am not a big seiyuu otaku, but over tiem I’ve gotten able to pinpoint most voices or at least roughly guess them.
I am also a guy who can memorize and be able to sing perfecly the lyrics to a song after reading them once and hearing the song 4 or 5 times. So maybe I’m just good with stuff like this naturally?
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I think it’s a skill you can improve with practice. What I do is spend a lot of time on ANN checking on seiyuu roles, then I watch (or rewatch) those anime they’ve appeared in, to learn their nuances. In a week or two I can pinpoint those seiyuu even without knowing the cast.
At any rate, I was only able to guess Akio Ohtsuka for Paprika when I was watching it a year ago.
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I totally empathize with you; I hate it when I figure out a voice and can’t tell anyone. Once I was in anime club, watching Cowboy Bebop for perhaps the first time since I had seen Kamen Rider Den-O, and I said “That Guy’s Deneb!!!” after I figured out that a minor character shared a voice actor with the Den-O character. Nobody else in club had seen Den-O, so my exclamation fell on deaf ears.
I can recognize a lot of characters I really like, even though I don’t actually know their seiyuu names save a few. The guy who plays Leo Shishioh on GaoGaiGar I can identify in other anime, but I still couldn’t tell you his name without looking it up. One of several persons I have this problem with.
One major exception to this is Seki Tomokazu. I always find myself surprised to discover that certain characters are played by him, because they sound so different. But that’s just one of the reasons his name is memorable for me; that he can modulate his voice beyond the capacity of my ears to recognize.
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I am horrible at the “guess the voice actor” game. I cannot always tell when it is Ayako Kawasumi for goodness sake. And that more than anything should be the clearest sign that I am poor at this game.
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I can recognize if the character is a seiyuu’s different voices for characters but I usually can’t identify the particular seiyuu without going to ANN or MAL first.
“THAT FAT GUY IS AMURO RAY”
This immediately made me think of Hayato.
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