One of the many memorable segments on The Late Show with David Letterman back in the day was “Fun with Rupert,” which began in 1994. The gist of it was that Letterman would send a man named Rupert Jee around with a hidden camera to bother strangers wherever he found them. Through an earpiece, Letterman instructed Jee to do […] The post That Time David Letterman Accidentally Pranked a Cartel Leader appeared first on VICE .