I am 50/50
 

I was thinking Memento, the computer guessed Bloody Simple (?).

I was thinking A Different World and it finally got it after about 25 questions.

I'VE FINALLY BEATEN THE COMPUTER!!! :D I have been trying to beat this thing since this post came up. Everytime it guesses the wrong thing and I think that I have won, it would claim that "17" or some other number of people had thought of that show/movie. Then it would provide a list of my answers to somehow imply that I was wrong. Well, I finally thought of one that the no one was thinking of and the computer didn't have in the database. The movie? HOUSE PARTY! (MY FAVORITE MOVIE!) :)