Saturday Night Live turned Pennywise into a tech bro on Weekend Update, pitching an AI startup called WeAllFloat.ai. Ben Marshall played the It clown as a startup founder on the October 31 Halloween episode, where his pitch involved AI agents doing his child-luring for him, each equipped with a digital balloon.
He’d supposedly come to discuss Gen Z wellness parties and promote having fun without drinking. That turned into a pitch for scaling his balloon routine through AI, complete with plans for an Austin loft and fellow “motivated young Christians.”
Marshall’s Pennywise described gathering “a little crew together of cool, like-minded, sober, predatory tech guys.” The appearance also became an intervention for Michael Che, with the clown calling Che’s recent stand-up special a “cry for help.”
