Yes, actually I do this all the time. While I think the total effort of a web server is about the same in most languages, an initial prototype is way easier in

Yes, actually I do this all the time. While I think the total effort of a web server is about the same in most languages, an initial prototype is way easier in a language like Python or Ruby. That's mostly because there's much less ceremony involved and all the bits you need are right there. As I work on the prototype though, I start to figure out if the language I decided at first will work well for it or not. Since I usually throw my first prototype out, with a fixed time to get it working, I'll end up picking a different language or not depending on my experience so far.