After Paul Reubens died, Conan O'Brien found an old birthday message: 'I was just stunned.'

Matt Wolf's HBO documentary Pee-wee as Himself explores the triumphs and trials of Paul Reubens, the actor-writer best known for his absurdist character Pee-wee Herman. There are too many revealing scenes to mention, but one casual, offhand moment—his phone alarm going off, prompting him to send some birthday texts—shines a light on Reubens the friend. "Today is a heavy birthday day because I have 12 birthdays today, including my eye doctor," he says with a sly grin. "I send a birthday GIF all day to people about every two or three hours, from sun up to sundown, from the time I get up."

This was a totally normal occurrence, as Conan O'Brien documented on his podcast in 2023. Processing the "devastating news" that Reuben had died at age 70 due to respiratory failure, the comedian reflected on those beloved birthday messages—and how they exemplified his warm, playful spirit.

"If he knew [someone] even slightly, he would fill their inbox that day with all these silly cartoons and memes about 'birthday'—old Disney cartoons, old weird memes about 'birthday,' cats falling into birthday cakes," O'Brien said. "He would do it all day long. It wasn't just me. It was anybody that he encountered he would do this for...We all just want to feel seen or recognized, and for someone like Paul to do that for so many people was just a gorgeous statement of who he was."

The former Late Night host also talked about one particularly special birthday gift: a video greeting that he received from Reubens one year prior. It was around six minutes long, "really funny," and "incredibly sweet," and it wound up buried on his computer. After Reubens' death, the admittedly un-tech-savvy O'Brien was rummaging around his hard drive, looking for a file sent by his online guitar teacher—and in a "surreal and magical" coincidence, he stumbled upon that old birthday salute.

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"I remember this message because I loved it so much and saved it," he said. "But I'd forgotten. It's just him talking to me and telling me—in a way, it felt like he was saying goodbye because it was him saying how much he values our friendship. I'm not gonna get into details about it, but I was just stunned...He went out of his way to tell people what they meant to him. He went out of his way to be sweet and kind...I'm sure he did that for a lot of people, and it made me realize, 'What a generous thing to do.' This was just a year ago, so he knows he's not well. To do that, to extend yourself like that, is such a gift because we lose people and have no idea...This was a nice thing he did. It sounds crazy, but it made me feel so much better. He just showed up on my computer magically and had this nice conversation with me."

As tributes flooded social media following Reubens' passing, many other celebrities shared fond memories of his uniquely personalized birthday messages. "Paul Reubens was like no one else—a brilliant and original comedian who made kids and their parents laugh at the same time," Jimmy Kimmel tweeted. "He never forgot a birthday and shared his genuine delight for silliness with everyone he met. My family and I will miss him."

Modern Family actor Eric Stonestreet posted the final birthday video Reubens sent him. "I hope your birthday today is beautiful and perfect," the actor says in the clip. "But I hope it's the first day of an amazing, wonderful new year for you that's going to bring you kindness, joy, love, happiness, health, wealth, luck, and beauty—and more than all those things, laughter and fun."