This specific screenshot however - a linked list - shows a situation where you most likely don't care about the exact structure like this - you only care that it's a list of elements, so most debuggers would show it to you like that - just as a list. The specific raw structure only obscures the parts you care about.
Visual Studio allows describing your custom data structures like this using XML files (https://msdn.microsoft.com/en-us/library/jj620914.aspx), or even custom graphical controls (https://code.msdn.microsoft.com/windowsdesktop/Writing-graph...) and gdb allows you to write a pretty-printer in Python (using an API which I can't find any documentation for :/ ), but it's all kinda clunky and still doesn't deal well with large amounts of data.
My ideal tool would be something that combines both of these things - you have
- An object graph that you can zoom in/out of that shows raw objects (just like in that DDD screenshot).
- An easy way to describe a custom view for your own objects (you can also switch to the raw view for an object, or switch between different defined views, etc.). Just like VS/gdb/lldb allow you to do, but a lot easier and more powerful. You could for example view a specific dictionary that contains complex objects in a tabbed interface, where the keys are tab titles, etc.
- A way to live edit these custom views - so that you can rapidly create them without restarting the debugger and restoring the state many times (Visual Studio supports this for the .natvis files).
- A powerful searching/filtering/transformation mechanism (e.g. for every object that satisfies this condition, show only this property and sort by that, etc.).
- Some way to save these configured views + filters + transformations, etc.
