Some time ago I found a fantastic internet-site which shows how evolution could have worked, if natural history had taken other ways. There are hundreds (or thousands?) of animals which could have evolved from known extinct or modern species, many with great pictures. They also invented some very interesting hypothetical ways of squid and nautiloid evolution. Just have a look at it:
http://www.bowdoin.edu/~dbensen/Spec/Baleen-squid.htm
http://www.unet.univie.ac.at/~a0000265/Spec/Ammonoidea.html
http://www.bowdoin.edu/~dbensen/Spec/Baleen-squid.htm
http://www.unet.univie.ac.at/~a0000265/Spec/Ammonoidea.html