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Billie Eilish convincing Conan O’Brien to play Slender Man is hilariously brutal

May 15, 2026
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What starts with a discussion about growing up not liking their names quickly turns into a brutal roast in the Conan O’Brien Needs a Friend video above, with Billie Eilish trying to convince the host he could play a perfect Slender Man. Yes, the terrifying, tall, suited boogeyman of internet urban legend.

“You come in here, you’re like, ‘Oh Conan, you’re so talented.'” responds O’Brien in mock outrage. “Oh really, my humor? My wit? ‘No! Your freakish size! You could be Slender Man!'”

Eilish, however, is undeterred. “You have such an amazing opportunity!” she says. “You could be so scary.”

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