akinator

[GameAndWatcher]

I thought of Terra from Mega Man V.  He guessed a Rachet and Clank character, Lumine, and Galaxy Man, but not Terra, I guess he's fairly obscure.

[Dataman]

...Apparently, this guy doesn't know who the Paint Roller is.

same with Astroman, it seems.

[Thunderono]

He can't figure out who the heck Big Arm is.

[Kapus]

Well, to be fair, Big Arm isn't that much of a character as it is a machine.

[Dataman]

Apparantly Astroman is in his database, he just didn't realize that that was who i was thinking of. the Paint Roller isn't though, so i submitted it.

[Rozark]

Apparantly Astroman is in his database, he just didn't realize that that was who i was thinking of. the Paint Roller isn't though, so i submitted it.

It knows who Morshu is.
MMMMMMMMMMMMMMMMMMMMMMMM

[Ceridran]

He got teemo. This is somewhat freaky to me.

[Xronim]

He can't get Nasir (Lagoon's Main Hero), i did all the answers that would lead to him, but instead it lead to Original Character, I outsmarted him.

[*Alice]

He got Lum from Urusei Yatsura right on his second attempt. Not bad.

[Ivory]

I tried Severa from Fire Emblem: Awakening. Got her on the second time.

Then I tried Leviathan from Zettai Bouei Leviathan (who is almost my avatar), a very new 2013 spring anime and couldn't figure it out.  

[Myroc]

You may be good, Akinator, but my obscure character knowledge surpasses yours.

Guessed GLaDOS, when I thought of SHODAN. (Really? SHODAN isn't that obscure. In fact, she used to be one of the more infamous rogue AIs before Portal came along and stole the spotlight.)
Guessed someone from the Silmarillion, when I thought of Ciaphas Cain.
Guessed someone whose name I do not recall, when I thought of Clunk. Similarly, he guessed Nathan Drake when I thought of Sheriff Lonestar. (Turns out he doesn't have any of the Awesomenauts in his database at all, so I'll be trying to teach him a few of them.)
Guessed Urza correctly. Fair enough, but I'm still ahead with 4 to 1.
Guessed Jon Irenicus, when I thought of Korax.
Guessed Cthulhu, when I thought of Nicol Bolas (though that was his second guess, so I'll call that a draw).

And then I kept failing to connect to the site, so I decided to leave it there, probably to resume later.

[Ceridran]

I beat him on my second time.

I guessed Varus, but he thought it was Fiddlesticks.

[Dataman]

Wow he's good.
he guessed Maxwell.
now to see if he knows any of his brothers...

[Bokan]

Well mine got pretty near to it

Bokan
Its a Russian living in the Taiga Woods ( Shaman )

and i got:

I think of
Sidartha Gautama/Buddha

[LlamaHombre]

He couldn't guess Flame Man, despite firing Magnet Man, Fire Man, Heat Man, Crash Man and Metal Man at me. For some reason he threw Fawful in there as a guess as well.