It guessed Skeletor from Masters of the Universe in 18 questions, exactly as many as it took to get Pluto, Mickey Mouse’s dog.
I stumped it with N.U. Unruh, he wasn’t in there at all. He is now, though. 
It took all 40 questions to get Elmore Leonard, but James Ellroy stumped it.
It amazed me with how quickly it got Illidan. I then proceeded to stump it with Ariabart Tytania from the Japanese space opera Tytania.
I stumped him on the first try with Tyler Clutts, FB for the Chicago Bears. I suppose in the game’s defense, there’s not going to be a lot of people thinking of him. So he’s in the database now, so I guess it’ll get it next time.
I stumped him with Cecil. He had him in the database, but my answers didn’t make it. And, unfortunately, when you go that far, you can’t look at your answers and see if I got some “wrong.”
It got planet jupiter in 20 questions, and its not even a real character.
I bet it didn’t get him, because it explicitly states that its target is real or fictional characters, not actual people. Had there been a movie made about Rickey Jackson it would have had you, just like it got me with Rudy Ruettiger, complete with Sean Astin picture.
Surprised me by getting Roy Greenhilt. The questions seemed like random guesses; “Is your character from Hong Kong?” “Is your character from a TV series?” “Has your character been to outer space?” The only question that seemed to target Roy Greenhilt was “Does your character use a sword?”. But there was no question about my character being in a webcomic or a fantasy setting or on a quest to avenge his father or even shaving his head.
I stumped it well and good with Mielikki, which is a Finnish nature goddess from the Kalevala. Apparently the Aesir are in the database however, because that’s what the guesses were based on.
I’ve only beaten it once, with sci-fi writer Gene Wolfe. It guessed Orson Scott Card and Dan Simmons. Some of my answers may have been wrong though.
Beat it again with English philosopher of science William Whewell
Order of the Stick is pretty well-covered there, though.
There’s also a psychological effect, here, in that the computer is playing the game better than we do. Humans playing 20 questions tend to ask questions for which we think the answer is probably “yes”, and so getting a lot of “yes” answers seems like a good thing to us. But the optimal strategy, which the computer is pretty close to, is to find questions that always cut your search space in half. With a good question, a yes or a no either one give you the same amount of information.
To use your example, a lot of characters who use swords are from Hong Kong. So by determining that whomever-it-is isn’t from Hong Kong, Akinator has narrowed down the field significantly.
I stumped it with Marjorie Merriweather Post. I even let it have several additional rounds (the “continue” option), and it still didn’t get it.
I beat it the very first time!
Al Pratt, the Golden Age Atom of the Justice Society of America.
OK, this is a funny one-- Akinator correctly guessed the Golem of Prague (after about 30 questions), but he expected the answer “yes” to “is your character a dinosaur”. Methinks someone clicked the wrong button, somewhere there.
To be honest, I can’t think of a single one. From China as a whole, possibly, but not specifically from Hong Kong.
Huh. Learned something today - to me Mielikki is a hunting/nature goddess and patron of rangers in D&D’s Forgotten Realms. Then again, considering the amount of myth plundering that goes on in there, I suppose it’s not exactly surprising 
It seems a bit US-oriented. It has not even heard of Lloyd Mangram. I had to add Lloyd Mangram to the database, like he was some schmuck.
Stumped it with Wallace Greenslade the announcer for The Goon Show