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.
 * The NCR troopers are easy to pickpocket. Just make sure you're hidden and quickly take the first thing that's in their inventory.
 * 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.
 * 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.
 * Another good way to get this Achievement quickly is to pickpocket empty ammo casings. This is deemed invaluable and is thus easiest to get away with. It makes no difference which faction, but it is easiest to go to Brotherhood or NCR camps and prey upon sleeping soldiers.

Hints

 * Sneak skill will decrease your chances of being caught while pickpocketing.
 * Having the follower Lily Bowen, who you can find in Jacobstown, is beneficial when pickpocketing because she gives the player the Stealth Girl perk while she is the player's companion which increases the duration of the Stealth Boy by 200%.