* SugarWiki/AwesomeMusic: Music/MarkMothersbaugh, Music/ToddRundgren, Music/DannyElfman, Music/TheResidents, Dweezil Zappa, Music/GeorgeClinton, and Music/VanDykeParks provided music for the show, while k.d. lang, Music/LittleRichard, and Creator/GraceJones sang in the Christmas special.
** The song that the gang dances to at the end of "front page Pee-wee" is pretty catchy.
* BigLippedAlligatorMoment: When someone says the secret word, '''EVERYBODY SCREAM!'''
** The OverlyLongGag of Roosevelt eating dog food for one whole minute also applies, as it's never mentioned or acknowledged again.
* HarsherInHindsight:
** The scene in "Rainy Day" where a policeman threatens to send Pee-wee to jail if he makes any more prank phone calls, and the scene in "Heat Wave" where Pee-wee plays as a Judge are this after Creator/PaulReubens got busted in 1991 for charges on indecent exposure and again in 2002 for charges on child pornography (the latter, thankfully, turned out to be a false alarm).
** The scene in "To Tell the Tooth" where Pee-wee is on a stretcher becomes this when you realize that Paul Reubens spent his final moments in Cedars-Sinai Medical Center, passing away in 2023 from the cancer that he was diagnosed with in 2017. Nobody knew about his sickness until his death. Reubens' apology for not letting the public know in advance was issued posthumously.
** Pee-wee lecturing Randy on smoking in "Ants in Your Pants" is this when you realize that Reubens was a heavy smoker for decades, and that this was very likely what caused his cancers that claimed his life in 2023.
* SugarWiki/HeartwarmingMoments:
** Throughout "Party," Pee-wee watches others open their gifts, and thinks he didn't get one. Turns out that they saved his for last: a new friend.
** The openings for the second to fifth seasons still have a few "legacy" shots from the first season's opening, all in exactly the same place as always.
** From the Christmas special: Pee-wee asking Jambi for a second wish is played for laughs, but Pee-wee uses the second wish to wish the viewers a Merry Christmas.
* HilariousInHindsight:
** In "Ice Cream Soup," Captain Carl is lost at sea, prompting Conky and Magic Screen to help him. They eerily foreshadow a modern car's GPS unit in the process--Conky explicitly uses a "satellite tracking device!"
** While reading off a Chinese pen pal's letter in one episode, Pee-Wee excitedly says "I know Kung Fu!" Look again at who played Cowboy Curtis to see [[Film/TheMatrix why this is funny]].
** Those freaky-looking toys on Pee-wee's toy shelf (for example, a dolly with a Literature/{{Frankenstein}} head) just might have been the inspiration for the mutant toys in ''WesternAnimation/ToyStory1''.
** While on the subject of Creator/{{Pixar}}, it's also possible that Roger the one-eyed, green-skinned monster may have had an influence on the creation of [[WesternAnimation/MonstersInc1 Mike Wazowski, another monster with green skin and one eye]].
** Could it be that Angus Scattergood in ''WesternAnimation/RockDog'' may have been influenced by Cool Cat of the Puppetland Band? Think of it: they're both white cats who play music, wear sunglasses and dress in black.
* HoYay: All over, but particularly Jambi, who John Paragon said he played as a "dishy gay man."
* MisBlamed: Contrary to popular belief, Paul Reubens' indecent exposure arrest in a Florida adult movie theater didn't get the show cancelled (though it did lead to merchandise being recalled, reruns getting yanked from the air by original network Creator/{{CBS}}, and Pee-wee Herman becoming a punchline to many a dirty joke both on TV[[note]]cf. ''Series/InLivingColor'''s "Pee-wee's Mugshot Doll and Pornhouse Playset" sketch on the first episode of season three[[/note]] and in real life). Reubens chose to end the show as he didn't want it to go stale from staying on the air for too long and he wanted to branch out and do other things.
* NightmareFuel: If you caught it on Creator/AdultSwim, you might find it more nightmarish than whimsical (of course, if this show scared you as a kid, it might trigger you in adulthood).
** Pee-wee's toy shelf from Season 1 was in a class all its own, combining creepy stop-motion, surreal claymation and ghastly patchwork abominations into a single big circle on the Venn diagram of things that freaked kids out in the 80's. It's not hard to guess why Clockey replaced it on the Playhouse wall for the rest of the show.
** The horrific, dead-eyed Salesman also disappeared after Season 1 for the same reason.
** Pee-wee got his very own talking doll when the show was in its heyday. It wasn't the usual CreepyDoll, but it took a turn for the worse when you pulled the string: his trademark scream was creepily rendered as the doll ''roaring'' at you.
** An episode of the short-lived "El Hombre" (with its chalkboard drawing characters already falling into creepy territory) had a girl trying to smoke a cigarette only to set her house on fire. The outside of the house becomes engulfed in one giant fireball, then the girl and her mother scream "¡Ayudame! ¡Ayudame!" while surrounded by flames.
** The creepy Advice Lady puppet from "Why Wasn't I Invited?"
* QuirkyWork: Wayne White, who helped create the set and several puppets and provided the voices and puppeteering for Randy, Mr. Kite and Dirty Dog of the Puppetland Band (all of whom he also made) admitted that marijuana was a big part of the creative process for the show, though the show's aesthetic is supposed to be based on 1950s-60s live-action kids' shows with bright colors and loud, energetic hosts.
** [[LampshadeHanging Lampshaded]] years later by WebVideo/TheNostalgiaCritic, who created [[https://www.youtube.com/watch?v=cLswjthJ2j4 a video on the top 11 drug PSAs]], which ranked [[https://www.youtube.com/watch?v=kHFnc_eV4Lg Pee-wee's infamous anti-crack ad]] at number one.
--->'''Critic:''' ''(showing clips of "Pee-wee's Playhouse")'' Look at this show and tell me it isn't somehow inspired by an illegal substance. No sober person could possibly come up with this! [...] [T]his is just a few weeks before the infamous movie theater scandal where Paul Reubens was found whacking off in public. Kind of a mixed message there, Pee-wee!
* RetroactiveRecognition:
** Creator/LaurenceFishburne as Cowboy Curtis.
** Creator/SEpathaMerkerson as Reba the Mail Lady.
** Creator/JimmySmits as Conky Repairman Johnny Wilson.
** Creator/AardmanAnimations animated the "Penny" segments.
*** The "Penny" segments were Craig Bartlett's first major project before he went onto make ''WesternAnimation/HeyArnold''.
** Music/CyndiLauper sang the theme song, albeit under a pseudonym (Ellen Shaw).
** Music/RobZombie and Creator/JohnSingleton both worked as production assistants.
** Creator/NatashaLyonne played Opal, a member of the original Playhouse Gang.
** Music/WeirdAlYankovic fans might remember John Paragon, aka Jambi, from his memorable supporting role in ''Film/{{UHF}}.'' Jambi's catchphrase was also heard in "Pretty Fly for a Rabbi," Weird Al's parody of "Pretty Fly for a White Guy."
** Rob Bragin wrote two episodes. Bragin is best known as creator and executive producer of ''Series/{{Proof}}''.
** Roger S.H. Schulman also wrote two episodes. Schulman is best known as co-creator and co-executive producer of ''Series/{{Jonas}}'' and for co-writing ''WesternAnimation/Shrek1''.
** Stephen Holman, who did the "El Hombre" segments, is better known as the creator of ''[[WesternAnimation/KaBlam Life With Loopy]]'' and co-creator of ''WesternAnimation/PhantomInvestigators''.
* SpecialEffectFailure: The show had some very painful ChromaKey throughout its run. Its most obvious in "Luau for Two," when Pee-Wee does a limbo move--he literally becomes a 2-dimensional figure (which some may consider to be very impressive for its time)!
** The ByTheLightsOfTheirEyes segment in the Pajama Party episode has some very dodgy effects, especially when Roger's cartoon "eye" moves into the lit section of the floor behind him.
* TearJerker: It's a small example, but more than a few people have admitted to getting sad at the closing credits and the melancholy ending theme - it ''always'' sucked when it was time for Pee-wee to go. (Though where did he head off ''to?!'')
* ValuesDissonance: "Open House" shows how to make sun tea as a snack. This was before public awareness about sun tea containing bacteria due to the tea being improperly heated. The scene was cut in the MGM/UA Home Video release and on Fox Family reruns, but it was reinstated with a ContentWarning for the DVD release.
* ValuesResonance: The most prominent theme throughout the series was that it's perfectly okay to be different, a message that's just as important today as it was in the '80s. Even better is that [[ShowDontTell this was simply demonstrated through the colorful, off-the-wall wackiness of Pee-wee and his friends, rather than preached to the kids at home]].
----