A game show needs to be a well-oiled machine, so there are usually multiple safeguards and security measures built into production to ensure that cheating doesn't occur. If the legitimacy of a show comes into question, audiences stop watching, advertisers drop out, and millions go un-won, so it’s important to keep things on the level. Still, despite preventative anti-cheating measures, a few crafty individuals have won big by beating the system. Here are a few of TV’s most notable modern day Robin Hoods. Michael Larson - Press Your Luck | 0:28. Charles Ingram - Who Wants to Be a Millionaire. | 1:32. Khaled El-Katateny - Millionaire Hot Seat | 2:29. Jack Barry, Dan Enright, Herb Stempel, Charles Van Doren - Twenty One | 3:08. Terry Kniess - The Price Is Right | 4:16. Website →.