Artful Pocketer

 is an achievement in Fallout: New Vegas which is awarded for successfully picking 50 pockets. The best way to do this is to grab a stealth boy and go to a heavily populated area and start pick pocketing people. You are not required to pick 50 different people's pockets, so for example stealing 50 pieces of ammo from one person one at a time (saving in between is recommended) will unlock the achievement.

Sarah Weintraub (Vault 21) has a pack of bubblegum in her inventory which can be pickpocketed over and over again. Stealing it from her while using a stealth boy will make getting this achievement/trophy very easy.