The #1 award in my list goes to Eclox+Doxygen+Graphviz+Mscgen. Yes, it is a single Eclipse plugin (Eclox) for Doxygen, and with two other powerful tools. It solves a typical engineering problem: “How to document my project? And how to keep it up-to-date?”.
Like many other engineers, I do not like to write documentation. Because it is painful. I want to write code and program. Writing documentation for it should be fun too. And it should solve the problem that the documentation does not match what has been implemented. I’m a big fan of the ‘single source’ concept: information has to be in a single place, and not copied and distributed among different places. And here my #1 helps me doing this.