I defeated it with Michael Moorcock’s Jerry Cornelius. And it took over 60 questions (and 3 wrong guesses) before it got Bernard Woolley from Yes, Minister…
I defeated him several times with webcomic characters, not the main ones, but he did guess a character from Las Lindas.
While I tested him with McPedro the cactus from Girls with Slingshots Akinator asked:
“Does your character drink their own urine?”
WTH? 
However he did guess it right! At the 25th question after asking if he was an internet character with a mustache and not human.
“Has your character ever bitten someone while playing soccer?”
I wonder what that’s supposed to narrow down.
Anais Nin (writer) Akinator took 68 guesses with two wrong guesses before getting it right.
It came up with Ralph Wiggum first when I was looking for BamBam, but after a few more questions, it got it right.
It took me like half an hour, but I finally got it with a character from an obscure Tumblr webcomic, Tobias and Guy. But i T fr EakI n guE sSe d Dil Howelter, and if you don’t know who that is, then your life must be very sad. But it’s a FREAKING SIMS CHARACTER THAT DAN AND PHIL (youtubers) CAME UP WITH. HOW?!?!?!?!!?!?
I’m guessing this guy but the Washington Post reports such antics aren’t all that unusual during the World Cup.
Why does he ask if your character likes pineapples? It asked me that about three or four times when I was thinking of multiple characters.
Well I defeated him with Grey Area , A General Contact Unit from the Ian M Banks Culture series
Now Akinator did guess a generic General Systems Vehicle (GSV) from the same series after about 12 questions, but not quite the same, ok it is a fine line, but damn it, it is so good I am claiming anything I can get.
Late last year, I was impressed that the Akinator got the killer from “Too Many Cooks” Too Many Cooks (short) - Wikipedia
See my post 16 above.
I put ol’ Aki through his paces on the works of British sf author Arthur C. Clarke today. Not too impressive:
60 questions - Didn’t get Vannevar Morgan, protagonist of The Fountains of Paradise. Aki asked twice each, “from Earth?” and “has tattoos?”
70 questions - Didn’t get George Hanley, a prominent character in Clarke’s well-known short story “The Nine Billion Names of God.” The very freakin’ first question was, “Connected to SpongeBob SquarePants?” Asked me twice each if he was fictional and was an adult man, and asked “Does your character have human skin?,” “…wear a bandana?” and “…Korean-Canadian?”
42 questions - Finally got Karellen, the top alien Overlord from Childhood’s End. Twice asked if he was from a videogame, and also asked “Is your character orange?” and “Is your character still in his band?” WTF?
50 questions - Didn’t get Robert Ashton, the art-thief protagonist from “All the Time in the World.”
70 questions - Didn’t get Alveron, captain of the alien starship in “Rescue Party.” Didn’t ask if he was an alien until question 68. Asked if the character was from a novel, TV, movie, song, comics or anime, but never asked if he was from a short story (come to think of it, Aki never asked me if any of these characters were from short stories). Also asked, “Is your character a penguin?” and “Is your character linked with the color orange?” WTF x2?
Stumped him four in the last two days, with two characters that were in the database (Charles Talent Manx from NOS4A2 and Samaritan from Astro City), and two who weren’t (Choco Kawagoe of Chocotto Sister and Maps Mizoguchi of Gotham Academy).
Apparently your answers were really close to some character who has a defined trait of liking pineapples.
You see, the way Akinator improves its database of characters and questions is that, when it can’t guess your character, it asks you to both put in your character (or pick it from a list if it knows about that character), as well as allowing you to add a question.
Unfortunately, it can’t tell that the same question has been entered multiple times if it’s been asked different ways. So if a character that Akinator kept missing is commonly known for liking pineapples, it makes sense that multiple copies of that question would be in there.
There may be an eventual algorithm to filter them out if they always get the exact same answer. meaning they are likely the same question. That would be smart. But, if so, it’s not hit its threshold yet.
OK, and I just stumped him with Rotwang (though the False Maria was one of the options shown, so perhaps he was getting close), but he got Freder.
Akinator figured out Brady Haran way before it figured out CGP Grey, which is odd.
Stumped it on Edwina Currie, fairly famous British politician . After it guessed Margret Thatcher, its questions went off into the weeds asking the same questions a few times.
It does eventually figure out that questions are correlated with each other, or that they’re not particularly useful (a question to which only one character ever answers “yes” is a bad question). But there’s an endless supply of new bad questions provided by users, so the filter’s job is never done.
Also, fandom arguments can really fuck him up.
‘Is your character in love’ is a pretty useful question… If you don’t have a situation like a character I tried earlier where half the fandom is taking the canon and word of god at their word, and the other half twisting them into pretzels to deny them.
I managed to beat it with the main character of Focault’s Pendulum.
I stumped Akinator with Jambi the Genie, from PeeWee’s Playhouse.