In general, it probably won't matter which one you use in most situations.
The main use case is this:
"Interface to global information about an application environment. This is an abstract class whose implementation is provided by the Android system. It allows access to application-specific resources and classes, as well as up-calls for application-level operations such as launching activities, broadcasting and receiving intents, etc."
https://developer.android.com/reference/android/content/Context.html
If you press "ctrl + b" on the object such as the View or Activity and everything it extends from, you will eventually get to the top. As long as whatever you're doing has what it needs then it should be fine. So for the typical things you will need you don't need to worry about it.