I'd start nice and easy..

Drop hints here and there. Magazine/Web articles on cubicle walls. Comments like "Ah, I'll just write a Perl script to do that". Make Perl a household name.

Emphasize that Perl is happily at home on a Win32 machine. Maybe he won't agree to a Linux box, but will agree to Windows running Apache and Perl. There are times when we have to compromise.

Bring in your 486 and show him how much power you can squeeze out of such a measly machine. Say "heck, I couldn't even run Win98 on it, and look -- it's a webserver/mailserver/etc. all in one. Let's see you do that with Win2000!"

Do learn ASP so that you can competently point out how Perl is better. ASP might come in handy anyway.

And, hey, nothing works better than plain, old, drop-by-drop brainwashing. Day by day, we're subverting one of the religious NT zealots in our department to say "Yah! Linux roolz!" with progressively less sarcasm, using the abovementioned techniques. Good luck! :o)