Pee Wee Herman’s 1980s Halloween Appearances on Letterman

Pee Wee Herman on David Letterman in 1984 on Halloween

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.

  • I was a big fan of Pee-Wee as a kid. I remember seeing his HBO special as a kid and my mother not knowing it was more aimed toward adults, so she let me watch it. It wasn’t bad and most of the jokes went over my head, but it is interesting to think he was more adult oriented at the time.

  • I caught it years later and was confused, I didn’t realize that he was meant for adults when he first started out!