Would you start learning Smalltalk?

Learning Smalltalk will give you a grounding in object oriented software development from the perspective of the man who invented OO (Alan Kay). The idea of a overlapping windowing environment came from Smalltalk.

A stumbling block to learning Smalltalk is that it is a message passing system with a strange syntax for flow control like:

i < 60
   ifTrue: [ self walk ]

It has a very mature class library that has a consistency I've not seen too many places. The class library in all environments (even commercial Smalltalks) has available source which allows you to learn from the masters of the language. When programming Smalltalk, I always ask the question how is it done in the environment.

Smalltalk is generally implemented in an image which is a live environment for all the objects in your system.

The interactive debugger really seperates Smalltalk from Ruby.

Seaside is the web development framework and has given Smalltalk a new spotlight. It is a continuation based environment that allows for intra-hit debugging and a smooth Rich Client type development experience (top application flow can be designed in a single method). It's integration with script.aculo.us has been done in such a way that it is easily called from within Smalltalk.

Would not start learning it if I had the time. Why not? Because it would be more productive and lucrative financially to learn C# or Java.

On the other hand if your a hobbyist, and would like to go on an archeological dig, then I'd suggest spending some time looking at the What, When, Why and how of smalltalk by researching Alan Kay. Fascinating story and an incredible person (after all, he earned the Turning Award). Then maybe play with squeak a little to get a feeling for the language. After this you might have a newly found respect/understanding of blocks, closures, and Object Oriented principles.

I know and use Smalltalk, have for about 15 years, still maintaining it, and would not recommend Smalltalk to a friend. Why not? Employment is a good thing to have and keep getting. Although you can learn a lot from Smalltalk you can't easily turn that into gainfully being employed in this day and age.

Also, you appeared to be excited over Seaside and I would assume the Seaside/GemStone partnership. I've used GemStone for quite some time and the two together are very appealing. I hope they can get the market share and momentum required to be successful.