I just chose Kaspar Hauser and it thought I meant Spartacus. Um, okay.
eta: And, stumped it with Jonathan Richman, but mostly because the other 133 people who picked Jonathan Richman had filled it up with completely wrong anti-information, such as that the guy who has written approximately ninety billion love songs about Boston was a New York musician, the guy most known to the general public for "There's Something About Mary" has never been in a movie, and the guy who wrote "My Little Girl Has A Full-Time Daddy Now" and subsequently had said no-longer-little girl sing backup for him has no daughters; also that he probably doesn't have curly hair or dark hair, and there's no consensus as to whether he ever sings on a stage. Come on! Unless "Jonathan Richman" is just a completely random name you pulled out of your ass, these are not difficult things to know with certainty, people! So either it's ass-pully, or enough people have played and gotten bored that now they're just fucking with the poor Akinator.
etaa, just to be fair, he did have his Velvet Underground love and a cursory attempt at New York musiciantude, but given that it was brief and couch-surfy and he came there from Boston, promptly went back to Boston, and stayed in Boston for a good long time afterwards, that's still not one hell of a lot of New York.