Artful Pocketer

 is an achievement in Fallout: New Vegas which is awarded for successfully picking 50 pockets.

Strategy

 * One of the easiest ways to get this Trophy/Achievement is by going to Vault 21. Sarah Weintraub has an infinite amount of beer in her inventory. (Optional) wait until she sits down at the desk, then use a Stealth Boy to decrease your odds of getting caught and just pick 5 at a time, then save, rinse, repeat.
 * Having the follower Lily which you can get from Jacobstown is good to have with you because her extra perk helps with stealth boys.
 * The NCR troopers are easy to pickpocket, just make sure you're hidden and quickly take the first thing that's in their pocket.
 * A good person to get quick pickpockets from is Manny Vargas when he is found in the mouth of the dinosaur in Novac, as detailed in this video.
 * The best way to successfully pickpocket someone is to make sure your agility level is high in your S.P.E.C.I.A.L. and also be sure to have a very high sneak decreasing the chances that you will be caught
 * You can easily obtain part of this challenge at the various NCR camps at night as there will be 10-20 troopers sleeping at the same time in open tents.