![\"Play\"\/](\"https:\/\/www.newsbeep.com\/ca\/wp-content\/uploads\/2026\/01\/1767377889_184_hqdefault.jpg\")
<\/p>\nOne of the many memorable segments on\u00a0The\u00a0Late Show with David Letterman\u00a0back in the day was\u00a0\u201cFun with Rupert,\u201d 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 and say crazy things to the different people he\u2019d encounter. Here\u2019s how a typical segment would go:<\/p>\n
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Successful as \u201cFun with Rupert\u201d was, it eventually ended after one of the people they tried to prank pulled a knife<\/a> on Jee. Somehow, that wasn\u2019t even really the wildest thing that happened over the years. During one show, Jee approached a large Hispanic man in Los Angeles who was wearing a Michael Jordan jersey. \u201cExcuse me, are you Michael Jordan?\u201d Jee asked him. The man responded in Spanish, saying that he didn\u2019t understand.\u00a0<\/p>\n Jee continued to harass the man, who was clearly not happy about being filmed. At one point, Jee offered the stranger tickets to the movie Showgirls as he angrily looked down into the satchel he had hanging from his shoulder. To top it all off, Jee pointed at him and yelled<\/a>, \u201cHey, everybody, it\u2019s Michael Jordan! Look!\u201d By then, the man was visibly upset about all the attention he was getting.<\/p>\n What Jee and the rest of the Late Show crew didn\u2019t know then was that the man they were pranking was Ram\u00f3n Arellano F\u00e9lix, a ruthless drug lord who founded the Tijuana Cartel. F\u00e9lix had a reputation for killing people who looked at him wrong and was known to keep a gun concealed in a satchel<\/a> that he wore regularly. Luckily for Jee, F\u00e9lix was in hiding at the time and likely tolerated Jee\u2019s antics to avoid capture. The police later killed F\u00e9lix during a shootout in 2002<\/a>.<\/p>\n","protected":false},"excerpt":{"rendered":"One of the many memorable segments on\u00a0The\u00a0Late Show with David Letterman\u00a0back in the day was\u00a0\u201cFun with Rupert,\u201d which…\n","protected":false},"author":2,"featured_media":384003,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[29],"tags":[49,48,12997,75,163391,163392,348],"class_list":{"0":"post-384002","1":"post","2":"type-post","3":"status-publish","4":"format-standard","5":"has-post-thumbnail","7":"category-tv","8":"tag-ca","9":"tag-canada","10":"tag-david-letterman","11":"tag-entertainment","12":"tag-ramon-arellano-felix","13":"tag-rupert-jee","14":"tag-tv"},"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/posts\/384002","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/comments?post=384002"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/posts\/384002\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/media\/384003"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/media?parent=384002"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/categories?post=384002"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/tags?post=384002"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}