While he's admittedly not nearly as creepy as the other mascots on this list, a man with a Ping-Pong ball for a head does leave something to be desired. Jack I. Box, mascot of Jack in the Box, stars in advertisements as the supposed founder, CEO and spokesman for the chain restaurant. He allegedly hails from a cattle ranch in Colorado and is married to a blonde woman named Cricket. Truth be told, the commercials are pretty funny. But still, modeling your mascot out of one of the most terrifying childhood toys you know, the one that features a menacing clown popping out of a box at an unexpected time is not a good idea.