This is a pretty straight forward achievement.
At any point in the game, go on the streets, equip your pistol, and go to a busy intersection and start shooting out tires on as many cars as possible. Shoot out a tire on 15 different cars for the achievement.
Citizens may start calling the cops on you while you are going for this. I would recommend killing them or using a Com Jam in order to block the call.
Keep in mind that this achievement is possible to be done over the course of the entire game, or during digital trips as well.
*Posting for Maka91, because he only played the Xbox One version.