What does "Rolling Four Deep" mean?

Answer 1

In terms of going somewhere, it means there are four people in the car. Three people in the car would be "rolling three deep," and so on.

Answer 2

In a larger sense what ever you are going to get into ----you got backup.

Two is better than one.

A cord braided of three won't break as easily.

With four one talks,
one looks at the opposition,
one looks over the shoulder of the opposition
and the last looks behind and checks the rooftops.

That's how we roll!!!