Alpha Geek asks whether Seaside is contender, along with Ruby on Rails. In his comments, I spotted this:

I guess my biggest problem with smalltalk is it's greatest asset. I'm just not a huge fan of Smalltalks images. It's not like you have a seperate smalltalk application, you have a full run environment that has been customized to perform some function.

Granted, it's been nearly eight years since I've dabbled, but I still haven't seen a Smalltalk optimizer that reduces the image size by paring out unneeded code, maybe because with smalltalk it's impossible to make that distinction.

So, I posted this response, also in comments:

VisualWorks, descended from the original Smalltalk-80 at PARC, has shipped with RuntimePackager for years - and before that, with a more basic stripping tool. Here's an example Smalltalk executable for Windows

After you run the installer, look in the install directory - you'll find bottomFeeder.exe, which is a 13MB executable. The development image that I use is 38MB.

I'm somewhat surprised that people aren't aware that you can, in fact, create Small Smalltalk apps. Smalltalk MT is fully compiled, and I know you can create Small apps with Dolphin. Heck, I've created executables that are under 4MB using VisualWorks - although I don't really strive for small executables. There's been a fair bit of research on this in Squeak, too - check out this page, for instance.