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This (sort-of) sequel to Pee-wee's Big Adventure, released in 1988, draws a great deal of inspiration from the classic story Pollyanna, which Paul Ruebens had wanted to do with this film's predecessor. This time around the director is Randal Kleiser (who also directed Grease and The Blue Lagoon), so the film has a different style (not to mention that there's a lot of jokes and references reused from the earlier film and the Pee-wee's Playhouse TV show).

Pee-wee Herman lives in a farm, with his animal friends including a talking pig named Vance. He has also invented trees that grow hot dogs. One day, a tornado hits the farm bringing a bunch of displaced circus performers with it. The performers include ringleader Mace Montana; his 5-inch tall wife, Midge, and an acrobat named Gina, whom Pee-wee falls in love with, despite the fact that he is engaged to Winnie, a local school teacher. Also, many of the other townspeople and the sheriff are not happy with the circus being in town, and threaten to have Pee-wee arrested, but Pee-wee has a plan of his own.

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Contains examples of:

  • Accidental Misnaming: Mr. Ryan called Mace Montana "Mr. Wyoming". Of course since this is Mr. Ryan, he likely doesn't care.
  • Anachronism Stew: There's plenty of modern and even fantastical examples of technology present, but the town Pee-wee lives near seems to have been locked in stasis since the 1910's. Though since the townspeople are old, they likely grew up around that time period.
  • Artistic License – Law: One has to wonder if Winnie thought through agreeing to marry four dudes, since the law tends to frown on polygamy. Granted, this is pretty easy to dismiss in a setting filled with talking pigs, five-inch-high women, and trees that grow youth-restoring luncheon meat.
  • The Big Damn Kiss: Between Pee-Wee and Gina. At least 90 seconds of screen time; other than the camera slowly pulling back, it is one continuous shot. The BGM even crescendos and ends in the middle of kiss, restarting halfway in. One can easily picture the composer shrugging and striking up the band again. They then do another right before and almost into the credit roll.
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  • Big "SHUT UP!": Gina constantly screams this to Pee-Wee when he tries to get her attention with a "romantic approach".
  • Blatant Lies: Mr. Ryan isn't even trying to hide the fact that he doesn't want to serve the Piccolapupula brothers, claiming not to have the items on their list even though they're all plainly visible behind him and then pretending to be closed.
  • Call-Back: Pee-wee puts his fingers on a girl's hair and looking at clouds.
  • Circus Episode: The Cabrini Circus is literally blown onto Pee-wee's farm by a storm. He has to help them deal with disgruntled local townspeople who do not like circus folk.
  • Continuity Nod/Mythology Gag: To Big Adventure:
    • "Why don't you take a picture? It'll last longer."
    • Pee-wee doing the "Tequila" dance on a tight-rope.
    • Pee-wee scares Andy (the midget) like he scared the street thugs.
    • Also like Big Adventure, it begins with Pee-Wee waking up from a dream.
    • Abraham Lincoln. In the first movie, Pee-Wee has a Lincoln dummy that flips pancakes, here he disguised himself as him.
    • "I love that story."
  • Disappeared Dad: Papa Piccolapupula.
  • Dream Intro: The film begins with Pee-wee singing on stage, then tries to sneak away by disguising as Abraham Lincoln, when that fails he gets chased by screaming fangirls into a dead end, leading him to fly away to what appears to be the town as he wakes up.
  • Foreshadowing: As shown in Pee-wee's lunch date with Winnie, there are signs which shows their relationship will not work.
  • Fountain of Youth: The cocktail wieners from Peewee's hotdog plant end up turning the elderly people into young children.
  • The Freakshow: Several of the circus performers are brought in from one. Pee-wee even tries his hand as a gallery exhibit.
  • Getting Crap Past the Radar: Kids wouldn't understand why Pee-wee is so excited every time he gets to touch a girl's hair, while their parents are probably impressed that Pee-wee managed to work a blatant sexual fetish reference into what's ostensibly a children's movie. There's also his remark to Winnie about two clouds resembling a train going into a tunnel, which she claims to not see (womp womp).
  • Here We Go Again!: Vance says this when Zha-Zha starts chasing him again when he's giving some advice to Pee-Wee.
  • Heroic BSoD: Mace Montana briefly experience this after first being told by the town they're not wanted. But seeing Pee-wee's scientific experiments inspired him.
  • Huge Guy, Tiny Girl: Exaggerated with Mace Montana and his wife Midge. He's a somewhat tall fellow, but she's downright lilliputian.
  • Hypocritical Humor:
    Mace: Lovely farm you have here. I hope we're not putting you out.
    Pee-Wee: Putting me out? Of course you're not putting me out.
    (Andy opens the door, accidentally hits Pee-wee. Pee-wee scares him. Looks back at Mace, and laughed like it was nothing.)
    • "Well she's certainly alright about the whole thing. Excuse me Pee-wee, my lunch dates have arrived."
  • I Have This Friend...: Pee-wee uses this when asking Mace about his problem. Though Mace likely knows it's Pee-Wee, and guessed correctly it was a "girl problem". Since he noticed Gina returning in anger and ignoring Pee-Wee who's looking at her.
  • Insane Troll Logic: One of the old ladies accuse Pee-Wee of sending Zha-Zha to kill her.
  • Interspecies Romance: Vance (pig) and Zha-Zha (hippo), whether Vance likes it or not. Of course, he appears to take a liking into her at the end.
  • Iris Out: With an iris back in to show Pee-Wee and Gina still locking lips.
  • Jerkass: The elderly townspeople. Mr. Ryan is the more obvious.
  • Karma Houdini: Pee-wee cheats on Winnie with Gina (but actually didn't mean to), receives no comeuppance and ends up with Gina in the end.
    • Winnie does give him a nice (if unintentional) burn by bragging at length about how much better off she is now that they're broken up, but that's it. They still decide to remain friends afterward and by the end, they're on the way to becoming in-laws.
  • Literal-Minded: When Pee-wee tells Winnie's students "Why don't you take a picture? It'll last longer.", they pull out their (old-fashioned) cameras and do just that.
  • Love at First Sight:
    • Between Mace and Midge, despite some people telling him their relationship wouldn't work.
    • Also between Pee-wee and Gina.
  • Manchild: Pee-wee's still as cuckoo as ever, but he receives a little Character Development here. He shows a lot of responsibility with his farm and altruism through his agricultural research, and his view of sexuality is a lot less childlike in this movie. He goes from being curious but nervous and put-off by sex to both wanting it with Winnie ("Those clouds look like a train going into a tunnel!"), and later getting it with Gina.
  • Meat-O-Vision: Pee-wee briefly turns into an enormous T-bone steak from a hungry lion's POV when it corners him. Luckily, Pee-wee's a Friend to All Living Things and easily tames it offscreen.
  • Negative Continuity: Call-backs aside, the film doesn't appear to follow up Pee-wee's Big Adventure as a true sequel. Pee-wee now has a career as a farmer and agriculturist, and neither his wacky home, his old friends, nor the bike he spent the last movie tracking down ever get a mention.
  • Non-Human Sidekick: Vance the talking pig.
  • Product Placement: Most can be easily justified by appearing in the general store, but the old lady at the townsfolk's celebration setting a bottle of 7-up down right in front of the camera sticks out like a sore thumb.
  • Omnidisciplinary Scientist: Pee-wee's inventions in his greenhouse.
  • Pair the Spares: Winnie ends up with the Piccolapupula Brothers in the end.
  • Screw Politeness, I'm a Senior!: The local townspeople. Likely justified since they had to deal with Pee-wee everyday, but that's no excuse telling off the Cabrini Circus they aren't welcome on their town.
  • Spiritual Successor: To Big Adventure, though only Pee-wee himself and composer Danny Elfman return.
    • Lynne Marie Stewart who played Miss Yvonne on the TV show appears and had a small role in the first film, appears in the supporting role of Zelda the Bearded Lady.
  • Stupidest Thing I've Ever Heard: When Pee-Wee tells a spurned Gina that he won't blame her if she never wants to see him again, she laughs her head off.
    Gina: You blame me?! (laughs back in her wagon) So funny I forgot to laugh!
  • Trademark Favorite Food: Winnie really loves her egg salad sandwiches. And so do the Piccolapupula Brothers. Pee-Wee lied that they're his favorite too, but he much prefers a cheese sandwich instead (to the point of flinging his egg salad clear over the horizon when she isn't looking).
    • She probably remains oblivious to this fact, as she threw both his and her sandwiches to the river in anger after seeing Pee-Wee cheat on her.
  • Your Cheating Heart: Subverted. Pee-wee cheats on his girlfriend, but didn't realize it until Winnie showed up (he had completely forgotten about her).
    • In any case, he ultimately realized he didn't really love Winnie as he originally thought.
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