[Edit limit] Unfortunately I see no way to check the log if you get to the end and defeat him. I got him on Kate Bush after 75 questions, but he kept asking me if she had played in a band, and I said yes even tho technically she’s always been a “solo” artist with a backing band.
Got him with Nathan Detroit. Thought for sure I was going to lose after the first guess was Sky Masterson but then he took a left and guessed Bugsy Malone.
Well, the Luggage stumped it once, but as it continued, it got it after about 40 questions 
It knew I was thinking of Ke$ha after 16 questions (although you all may have only needed one question to know that). It was a mere formality after question 13, when it asked if my person ever wakes up in the morning feeling like P. Diddy.
For Dan Rather, it took 23 questions.
Erik Estrada: 24.
Bob Barker: 24.
Magic Johnson: 13.
I stumped him with Dick Fick (former basketball coach at Morehead State).
Just stumped it with Bjørn from Hey, Wait by Jason, and added him.
I’ve previously stumped it with Sara Louise Bradshaw, the main character from Jacob Have I Loved. I added her then, but I’m trying her again now, and haven’t been able to get it to guess her yet. A moment ago, though, it suddenly declared, “I know who you are thinking of, but this is not for children” or something, and wouldn’t let me continue, so I started a new game. Weird.
Stumped it with Paul Lazzaro, from Slaughterhouse Five
Grr! Just got that message again! It starts, “Guessed Right One More Time”. No, you didn’t either! What the hell, man? You can’t just declare victory. I deem this lame, and shall play no more.
It nailed Lady Jane Grey, Douglas Brackman (L.A. Law), Laura Petrie, and Hamlet’s Ophelia.
Stumped it on Carl Anderson (current Supreme Knight of the Knights of Columbus) and Annika Settergren (Pippi Longstocking’s neighbor).
Stumped Akinator with Sergeant O’Leary, who’s “walkin’ the beat” in Billy Joel’s Movin’ Out.
Akinator then took 69 questions to correctly name Mac Tonight. Incorrect guesses were the Little Caesar’s pizza man and the Arby’s Oven Mitt.
Winston Spencer Churchill proved a little thorny, as he was awarded honorary American citizenship. And the Akinator has him down as not being born in a famous family, and a few other errors.
What, so they’ve changed it to where the questions keep going forever instead of stopping at 40?
And, based on what’s stumping him now, it sounds like, with more information, he’s gotten a lot worse. I specifically remember getting answers “wrong,” because I apparently knew more about the character than the average individual, and he still figuring it out–it just took him a while. Still less than 40 moves, too.
The way Akinator seems to work now, you must think in Family Feud style terms–what do most people think the answer is, rather than what the technically correct answer is.
Does anyone remember the Burger King promotion that had a similar “Darth Vader” 20 question site? After a few questions, the King would whisper in Darth Vader’s ear and he would amaze you with his answer.
I think the site was sithsense.com/org or something similar but appears to be offline as far as I can tell.
Was pretty freaking amazing.
It got me in 34 questions with my first go of Krypto, Superman’s dog, but then I stumped it both times with Billy The Cat from The Beano and The Brown Bottle from the Viz mag.