Using callout labels in ArcMap?

Is there a way to automate the placement and the text based on a field using callout labels?

One thing I've tried, which is quite cumbersome, is to convert the graphical objects after they have been drawn to an annotation class and then spatially joining the new features to the points they are labeling, then calculating the text field with attributes from the joined table.

I'm really hoping there is a way to generate box/callout labels in a more automatic fashion. I don't want to have to draw all several hundred callouts.

Software Version: ArcGis 10.3