6. Conan O’Brien vs. Madeleine Albright
In 2014, witty comedian Conan O’Brien had the tables turned on him when he was outsmarted on Twitter by diplomat Madeleine Albright. O’Brien had tweeted “I picked out my Halloween costume. I’m going as slutty Madeleine Albright.” Albright quickly retaliated with a perfect response: “I’m considering going as hunky Conan O’Brien – but that might be too far fetched.” She then followed it up with “Never get into a word war with a diplomat. We talk even more than comedians.” O’Brien admitted defeat, tweeting “Damn – whenever I go toe to toe with Madeleine Albright, she always wins.”
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