Regarding your pixel skills I'd say it's pretty well made, AA is cool and there's contrast to most of it. Although if you look at the image at 1X, the 2 lightest shades of gray you've used merge together...
I think it really works well using b&w on hitler/chaplin (Mr.Peanut?) pieces, for the whole classic movie/photo feel. Well done.
For the icon design itself, I wouldn't say it looks like a eyedropper at all. For starters, it's too tick... looks more like a condom or a pen (sorry, it does!
). Graphics programs icons (I'm assuming that's what it is) should communicate quickly what tool they represent. Of course I could see the bridge between a man wearing this kind of hat and an eyedropper tool after a while, but some ideas just won't read well (specially too elaborated ones) when you've to draw them on such a tiny space.
I'm not saying this particular idea wouldn't work, but I think it doesn't as is. Make the base eyedropper look more like one (thiner and taller) and then add only the absolutely necessary human features, making sure your pic don't get too cramped.
