Paul Reubens and Joe Manganiello first met in 2011 at an Emmys party hosted by HBO. The star-struck Manganiello saw his hero in the crowd and made his move, risking being ambushed himself in his excitement to get the chance to meet Reubens. “Those parties are usually really difficult because it’s just a room full of people who want to take selfies,” he told The Moveable Feast. “If you want to go to the bathroom, it’s going to take you an hour-and-a-half to two hours to get there. You usually go in, sit, and hide. But my publicist nudged me and said, ‘Oh my God, it’s Pee-Wee Herman. I thought, ‘This is my only chance, I’ve gotta go say hi.'”
What could have just been a quick photo-op turned into more. Manganiello and Reubens stayed in touch after that first meeting, and Reubens kept him in mind when working on the script for “Pee-wee’s Big Holiday.” Manganiello was instantly on board when he heard about the film. “I told him I didn’t even have to see a script — I’d do it,” he told USA Today. “There’s no bucket list where you write down, ‘Play in a comic duo with Pee-wee Herman.’ I still cannot fathom it.”
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In the film, Manganiello plays a fictionalized version of himself who becomes friends with Pee-wee, their on-screen camaraderie echoing their real-life friendship.