When Late Night with David Letterman went on the air in 1982, an agreement was made with Johnny Carson. The show - hosted by David Letterman - couldn’t be an exact replica of The Tonight Show. Guests were a big part of this. There were “Johnny guests” and then there were “Dave guests.” “Dave guests” were essentially those who were either a “nostalgia” booking or a young comic who maybe wasn’t the right fit for Carson.
These oddball personalities included people like Gilbert Gottfried, Sandra Bernhard, Andy Kaufman - who to be fair did appear on Carson about five times -, Harvey Pekar, and Pee-Wee Herman.
From the start, Herman - played by Paul Reubens - was a natural for the show. It was a mix of high intensity and sincerity that was not unlike that of Kaufman. At the time, you weren’t seeing someone like Herman on television. That’s what made him the perfect guest for David Letterman.
The origin of Paul Reubens' character "Pee-Wee Herman"
Herman was a creation of Paul Reubens that originated in The Groundlings improv group in Los Angeles. Herman created the character with Phil Hartman, and after a while, Herman gained a notable cult following in and around Los Angeles. This led to a successful run at The Roxy Theater, where he transformed the famous music venue into his infamous playhouse, doing evening shows for adults and matinee shows for kids.
By September 1982 - a mere 6 months after Letterman first went on the air on NBC - Herman made his first appearance on the show. His manic and energetic enthusiasm was a perfect contrast to Letterman’s more wry and sardonic style of humor. It made Herman a fan favorite, and he wound up going back on the show countless times over the years.
After Pee-Wee’s Big Adventure, for some reason, Herman stopped going on the show. In 2001, Reubens appeared on the show out of character for the first time, which he repeated two more times. But sadly, he never went back on in character, despite doing so on basically every other late night show.
A few years back, a two-and-a-half hour compilation of all of Herman’s appearances with Letterman wound up on YouTube. We can’t think of a better way to pay tribute to Pee-Wee Herman than with his most infamous late night talk show appearances.