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 and say crazy things to the different people he’d encounter. Here’s how a typical segment would go:
Successful as “Fun with Rupert” was, it eventually ended after one of the people they tried to prank pulled a knife on Jee. Somehow, that wasn’t 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. “Excuse me, are you Michael Jordan?” Jee asked him. The man responded in Spanish, saying that he didn’t understand.
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, “Hey, everybody, it’s Michael Jordan! Look!” By then, the man was visibly upset about all the attention he was getting.
What Jee and the rest of the Late Show crew didn’t know then was that the man they were pranking was Ramón Arellano Félix, a ruthless drug lord who founded the Tijuana Cartel. Félix had a reputation for killing people who looked at him wrong and was known to keep a gun concealed in a satchel that he wore regularly. Luckily for Jee, Félix was in hiding at the time and likely tolerated Jee’s antics to avoid capture. The police later killed Félix during a shootout in 2002.
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