PIctureboxes them selves are not transparent. Transparent controls a re a major point of contention in .Net.
Just use 1 picturebox and use GDI+ code to draw the images in the right order onto the picturebox. Here's a demo (see attachment). The background is passed to the picturebox during the load event so this means you only need to draw the foreground (transparent) gif manually. You can draw as many transparent gifs like this as you want they'll just pile up on top of each other.
Please look at the two images in the Bin folder before you run this demo, then you'll understand whats going on.
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