I've got rather distinct question - I'd like to run Smalltalk on a production server without using graphical interface. Is this possible with VW or Pharo (maybe even Squeak)?
I've got a VPS hosting without X and would like to have few websites running on Smalltalk, while developing them locally with full-blown Smalltalk env, including GUI.
Don't forget that there are also Smalltalk environments that are specifically designed for headless operation on a server, e.g.:
One of the specific design goals of Pharo is to divorce the development environment from the core image, for easier deployment, however I don't know how far this effort has come nor whether it also includes removing the GUI entirely.
I'm not sure about VisualWorks, but I wouldn't be surprised if they had a headless mode.
A little bit further out in left field, some people consider Ruby to be "Smalltalk for the Unix server". Although, of course Ruby is a much different and much less beautiful language than Smalltalk.
Have you tried asking on the Seaside mailing lists? They must deal with this stuff all the time. Avi Bryant's company Smallthought Systems, for example, runs both DabbleDB and trendly off Squeak.