Lets try 3 out of 5.
Harold from Harold and Kumar

Its first guess was Orgasmo then after a bunch more questions it finally gave me Harold Lee. That's a stump in my book since it didn't get it the first try.

Second try is the Blue Beetle... DAMN IT FIRST TRY! That is 50/50

Raven from Teen Titans (I just want the web genius to provide a sexy picture now).... it got it but it wasn't a sexy picture. One more and it wins.

Katie Morgan... Ha it failed with Jenna Jameson but gave me the answer a second time around but that is still one for me. Again 50/50 game maker now.

Chuck Norris will be the decider... Oh god I've been sent back in time since Akinator got it right, but Chuck Norris felt us to be unworthy to take his name as part of a game. Oh no, I can feel the pain from the kick being sent back in time too now. I need to hit send now bef

lolz it took him 3 wrong guesses to guess that it was sasuke XD

He knew that I was talking about Lady Gaga... HOLY CRAP!

i beet it with Kurgan (Highlander)couldnt guess it, it seems like he might use your search history i dont know, he guessed commander keen way to fast

26 tries to get Han Solo, with one wrong guess of Shepard from Mass Effect.

I stumped him with Oderus Urungus from GWAR

I forgot all about this!
I think it guessed mine more often than not.

It very good program! I know characters that surprised it knew, but on second attempt, i tripped him up bye thinking the character Charmy Bee. Obscurity is the key!

OMG HE KNEW IT he knew it was the man with no name (Clint Eastwood) SOO AWESOME ! THANKS FOR SHARING !