Ah, WebObjects. In a lot of ways, it was the Ruby on Rails of it's day. It was one of the first integrated, opinionated platforms with all the tools to build web sites backed by a database. Architecturally, it was years ahead of the first Java application server platforms; the persistence model so much better than the first iteration of enterprise Java Beans.

Its major drawback, in the early days at least, was that it was designed as an Objective-C framework. By the time I started using it (around 2000), Java was supported, but it was clearly an afterthought and you dealt with a buggy bridge to ObjC components and Objective-C-isms all over.