Does he actually give up or is beating him having him guess wrong?
I thought Chip from Chip and Dale and he had 2 wrong guesses, and eventually he said Chip and Dale (I think after question 70 or so).
He really makes odd logical jumps sometimes, another time I thought Max from Sam and Max and he asked me if the character was white, and had long ears. I thought wow he is definitely going to get this fast, he chose the Arbiter from halo.
Edit: Well I'm convinced this genie is powered by evil, he was able to guess Ax from the animorphs in 20 questions.