Buttonhole Puzzle
This simple trick involves a pencil with a loop of string. The loop is a little too short to reach around the far end of the pencil. The set-up is quickly attached to the buttonhole of a spectator, and the goal is simply to remove it. Although attachable in just a few seconds, most individuals will not figure out how to remove given hours.
The Buttonhole Puzzle is a late 19th-century creation of the famous American puzzle master, Sam Loyd. The story goes that he created the puzzle for the New York Life Insurance Company for marketing purposes. The original version consisted of a small stick resembling a policeman’s Billy club and a green loop of cord that was shorter than the stick. Insurance agents would attach the device to a customer's shirt or jacket buttonhole and create a memorable interaction since, while easily attachable, it is almost uniformly very hard to remove. It was later commercially produced in the 1930’s by James J. Sanders of the Sanders Manufacturing Company under the trademarked name of the “Magic Holetite Pencil”. These can still be purchased at many online stores.