Ruby on Rails---------(then Python,-------- then Perl) Ruby is easier to pick up with a much more active community. It really depends what you want to build:

Ruby on Rails---------(then Python,-------- then Perl) Ruby is easier to pick up with a much more active community. It really depends what you want to build: Python- If you need to build a site quickly that is mostly information based such as a blog or some kind of editorial site. I'd choose python with django. The automatic admin section is great for this type of task. Ruby- If you need to build something with a lot of popular features (twitter, mash ups, simple shopping carts, etc..) and don't have time to really learn every little detail. Ruby using Rails might be a good solution as there are thousands of demo and live applications out there to borrow from. Should reduce your development time. I throw out an line of demarkation....For example comparing the ways that Python and Ruby address Meta-programming, I think, will illuminate which for you is more interesting (which fits your brain better) I use Ruby on Rails the most. In the end...learn them all.