He got Bruce Lee
I thought James Hetfield, he guessed "James Woods (Family Guy)" Close in name, but not in anything else.
I figured out how it works though. It has a database of well known people and attaches them to certain answers. Like for Bruce Lee, he is marked as a dead martial arts expert. It searches through the database and eliminates certain people depending on your answers. It won't say Chuck Norris if you say yes to the "are they a singer" option, for example. If it gets something wrong, it asks who you were thinking of and modifies its tags accordingly.