Pee Wee Herman was a staple of my childhood, but at the time I didn’t realize that he appealed to adults too. In fact, the character was made to entertain adults rather than kids. I was far too young to ever see him on Letterman, so I was pleasantly surprised to find these clips of him making two special Halloween appearances on David Letterman in 1983 and 1984.
In 1983 Pee Wee makes his appearance in a pirate costume where he shows off some Halloween props and generally is all Pee Wee while Letterman provides his dry, sarcastic responses. Besides the couch stuff, Pee Wee also has a special laboratory sequence. It’s a must watch for a Pee Wee Herman fan.
1984 appearance where he’s dressed up as a devil and of course, there’s plenty of devil puns. This one has worse audio quality, so that’s a shame. You get to see a copy of Barbie Magazine. Later he shows Dave a Gremlins cereal box and some Gremlins toys. Pee Wee pretty much pulls out all the different Gremlins merchandise available at the time. Talk about a heaping dose of 1980s nostalgia!
In 2011 Pee Wee appeared on the Jimmy Kimmel show for a Halloween appearance dressed up as a Pee Wee Dracula. While not carrying the nostalgic fun of the Letterman appearances, it’s cool to see Pee Wee up to his old Halloween tricks and treats.