- Box Office Bomb: Budget, $20 million. Box office, $15,122,324.
- B-Team Sequel: Tim Burton turned down the chance to direct, as he was transitioning from completing Beetlejuice to beginning pre-production on Batman (1989).
- The Cast Showoff: The musical number Pee-wee sings in his dream at the beginning of the movie really is performed by Paul Reubens himself, who it turns out has a surprisingly good singing voice when out of character.
- Creator Killer:
- This was the second to last film produced by Richard Abramson; he never did another film after the 80's ended.
- This film also began a slow death for Paul Reubens' career as Pee-wee's Playhouse stopped making episodes in 1990. Not helping matters was Paul Reubens' infamous nudie theater incident the year after. It would be a quarter-century before Netflix revived Pee-wee Herman on a visible basis, making this film something of a Franchise Killer on top of it all.
- Real-Life Relative: Two townsfolk, Herman and Honey, are played by Milton and Judy Rubenfeld, Paul Ruebens' real-life parents.
- Romance on the Set: This happened between Valeria Golino (Gina) and Benicio del Toro (Duke the Dog-Faced Boy), who remained together for four years.
Trivia / Big Top Pee-wee