I think this collection of icons and associated categories would be bother more interesting than the current set and more useful. Of course, some of the existing categories (like MacPerl) would stick around.
ActiveState
Activestate is symbolized by this lunatic who represents the guy who thought that ActiveState and Microsoft were conspiring to destroy Perl. The corncob symbolizes backward compatibility because when a cow swallows a corncob, it sometimes gets stuck and blocks everything else from moving through. Beta Software is a toy train because beta versions are usually toy versions. Forked Projects (which I imagined would apply to things like Topaz and Sapphire) is a picture of a two-headed sperm. Occasionally calls go out for old archive files, such as obscure versions of Perl or the lost source for Sapphire; these items are filed under Lost and Found, which depicts Jimmy Hoffa. Perl 5 is symbolized by its most characteristic feature, the glob. Psychology is of course Sigmund Freud. Punctuational Issues (remember when there was a lot of discussion of _ vs. . vs. -> in Perl 6) are denoted by Kudzu. The icon for Standardization and Standardization Committees depicts the la Brea Tar Pits. Threats is the Redeemer, a shoulder-mounted guided nuclear missile from the game Unreal Tournament. The rest are supposed to be obvious. :)
If anyone actually things any of these would be a good idea (ha!), I'll rescale them to the appropriate size and make the backgrounds transparent if necessary.