It was fun, but it needs work though.
A fun game, but flawed in a couple areas.
For example, some of the acceptable answers were somtimes too obtuse, and sometimes too open.
I answered rabbit to the "There she is" and the "Walking in the woods" silhouettes, and they both were accepted. Perhaps some form of distinction could have been in place, or perhaps you could have chosen characters that weren't so similiar.
Another gripe of mine is the number of repeated series. I realize you have limited characters to work with, but Meatboy, Dr Fetus, and Bandage girl? Really? Hank, the Clown, Jesus, and the Sherrif? That's a bit much.
Your choice of silhouettes was for the most part decent, but I noticed a lot of very similiar looking circles, and near shapeless masses. Someone who spends all their time on NG might be able to indentify them, but for the average person, it is hard to tell the difference between a blob with rounded edges or a blob with slightly curved edges.
And finally your hint system. You get 4 everytime you play, and even you get a score deduction, some of your hints were too helpful, like for the silhouette of Samurai Asshole. You literally put Samurai Asshole as the hint for that character.
To be fair I had a lot of fun playing this, yey I was still annoyed by a few things.
Good music choices, solid programming, and a good concept.
Keep up the good work.