Dynamic languages win in the worse-is-better department. They're easy to implement and easy to learn. You can get a beginner up to speed in a language like Ruby or Python very quickly. This creates a grassroots effect that builds libraries and community around the language because many of those beginners gradually become experts. Dynamic languages are also generally more expressive.
There are definitely some downsides too though, and static languages have gotten a lot better in the last ten years. After many years of working almost exclusively in dynamic langs I'm enjoying having the help of the compiler again in the Scala hacking I've been doing.
Maybe so but the kind of type system that it takes to make a static language as expressive as a dynamic language has some inherent complexity you're not going to be able to eliminate. Static languages can be a bit of a harder sell too because the benefits of static typing aren't as apparent on smaller codebases.
While the type system might be more complicated, programs are simpler. Dynamic languages often need runtime checks dealing with types, and /that/ complexity is there in either case. Static languages just make a pretty interface for it.
There are definitely some downsides too though, and static languages have gotten a lot better in the last ten years. After many years of working almost exclusively in dynamic langs I'm enjoying having the help of the compiler again in the Scala hacking I've been doing.