If you want to get introduced to Smalltalk and happens to have a Windows machine, check out Dolphin Smalltalk http://www.object-arts.com/ http://www.object-arts

If you want to get introduced to Smalltalk and happens to have a Windows machine, check out Dolphin Smalltalk http://www.object-arts.com/ http://www.object-arts.com/. Many years back, I tried Squeak a couple of times and it didn't click. Dolphin Smalltalk did that for me (and I then went back to Squeak due to other reasons). It has a well-designed, compact class library and a decent UI. I'm not sure if it has been updated to keep up with Windows, but it's a great start.