The second Western episode in the series.
This episode contains examples of the following tropes.
- Accidental Pun: When Tigger tries to tell the others that he and Pooh re-assembled the whole "kit and caboodle" of the exploded train, he says, "I tell ya, we put the whole kit and caboose back together, and left it right there."
- Acting for Two: In-Universe. Gopher has a dual role as a prospector and a judge.
- Affably Evil: Piglet, Rabbit and Eeyore are the antagonists of the Western fantasy and eventually drop this role once the locomotive rampages the town. But while Piglet and Eeyore have a lot of charming qualities, Rabbit is certainly a vindictive jerkass.
- An Aesop: Lampshaded by Piglet: "But borrowing without asking is bad, too, especially if you don’t say 'please' and 'thank you'."
- Artistic Licence – Physics: In reality, the train simply would have crashed through the handcart instead of exploding upon impact.
- The Bad Guy Wins: Subverted. Piglet succeeds at arresting Pooh and Tigger and while Pooh’s name is cleared, Tigger is let off with a warning.
- Banana Peel: In the climax, Tigger stops the train entirely by throwing a banana peel onto the tracks, causing said train to crash.
- Borrowed Without Permission: Christopher Robin goes downstairs for lunch. Before he goes down, he tells his friends not to touch his electric train until he gets back. Tigger wants to play with it, but Pooh tells him not to. He tells Pooh that he's going to borrow it without Christopher Robin's permission.
- Bullying a Dragon: Rabbit constantly insults and belittles Pooh and Tigger. He even tells them that they are going to get just what they deserve.
- Cardboard Prison: Played for Laughs. The jail cell in the fantasy not only has Widely-Spaced Jail Bars, but also has no back wall. Pretty much the only thing keeping anyone in is the fact they know "being in jail" means you're not supposed to leave.
- Character Development: Piglet's self-esteem as sheriff has come a long way since his encounter with Nasty Jack.
- "Could Have Avoided This!" Plot: Directly mentioned by Rabbit at the end of the episode when he says if Tigger hadn't train-napped in the first place, the plot of the episode would not have taken place.
- Cowboy Episode: More like Outlaw Episode since Pooh and Tigger are train robbers.
- Curb-Stomp Battle: A crazy steam engine vs. a piglet for a sheriff? No contest.
- Drives Like Crazy: Tigger is an absolute novice when it comes to driving steam engines.
- Final Boss: The Western fantasy concludes with Tigger stopping the locomotive that he reconstructed.
- The Great Repair: Tigger's crude reconstruction of the train leads to the steam engine looking like something out of a surrealistic painting.
- Hero Antagonist: Piglet, Rabbit and Eeyore are the sheriff and deputies who uphold the law.
- Hope Spot: After escaping prison, Pooh and Tigger decide to redeem themselves by fixing the train, so as not to turn themselves in. But after Tigger rebuilds the locomotive, it goes off on its own for no apparent reason, Piglet captures the two in the high country and with no train to be seen in sight, both Tigger and Pooh end up in jail.
- Jerkass: Rabbit is disdainful towards Pooh and Tigger for understandable reasons.
- Just Train Wrong: This is Played for Laughs in the show's usual fashion...
- Rabbit and Tigger invoke this in the opening scene when they notice Christopher Robin's toy train lacks a propellor and rudder.
- In the Western fantasy, the tender seems to lack a water tank. Tigger can walk through the whole train even though it includes a boxcar, and the locomotive comes equipped with a brake pedal like an automobile would have. Then again, as Pooh puts it, "It's a fantasy."
- Jerkass Has a Point: Rabbit, again, after telling the others that Tigger is still a "train-napper".
- Knight Templar: Rabbit's aiming to bring law and order to the West and capture the Hole-in-the-Head Gang, by any means necessary. The same also applies to Gopher in his role as the judge.
- Lampshade Hanging: In a rare moment of intelligence, Pooh confirms twice that he is aware that he is in a fantasy.
- Lazy Mexican: Eeyore certainly resembles one, complete with a sombrero as well as the fact that donkeys are sometimes a personal form of transportation in Mexico.
- Limited Sound Effects: That Stock Sound Effect of a Bomb Whistle (originally a Hanna-Barbera effect) is heard seven times in the first act alone, and it gets pretty repetitive.
- Loophole Abuse: "I'm not gonna touch the train, I'm gonna touch the controls!" says Tigger even though Christopher Robin told them not to touch the toy train set.
- Nice Job Breaking It, Hero: Rabbit lampshades this after the locomotive's defeat. Had Tigger not rebuilt the engine, the climax would not have happened.
- Non-Fatal Explosions: The train violently blows up while colliding with Sheriff Piglet's handcar, but nobody is even hurt in the explosion, let alone killed.
- Oh, Crap!: Piglet when Tigger busts Pooh out of jail, complete with his catchphrase.
- Outlaw: Pooh and Tigger.
- Pinkerton Detective: Rabbit certainly resembles one, and his role appears to be a Shout-Out to real-life example Charles Siringo.
- Punch-Clock Villain: Piglet is a decent guy, but he wants to capture Pooh and Tigger simply because it's his job.
- Recycled Soundtrack: Some music originally written for "Paw and Order" gets reused during the Western fantasy.
- Red Oni, Blue Oni: Tigger's exuberant scheming is nicely balanced by Pooh's laconic moments of Genius Ditz.
- Resurrect the Wreck: Tigger and Pooh decide to rebuild the train (or the engine at least) in hopes of clearing their name.
- Runaway Train: Much of the Western fantasy in the first act plays this trope out when Tigger and Pooh end up unable to control or stop the train as it keeps going faster. This also happens for part of the second act when Tigger attempts to Resurrect the Wreck, only for his crude reconstruction to start speeding through town on its' own and wreak havoc. But since this is Winnie the Pooh, Hilarity Ensues, and nobody gets hurt when the train eventually crashes (twice).
- "Shaggy Dog" Story: By the end of the Western fantasy, Sheriff Piglet is saved and lets Tigger off with a warning, but the train has been completely destroyed once again (Fortunately, Christopher Robin's toy train is just fine in reality).
- Shout-Out: The episode’s title is based on The Good, the Bad and the Ugly with some shades of Butch Cassidy and the Sundance Kid found in the plot. In addition, Tigger and Pooh's Hole-in-the-Head gang is loosely based on the Hole-in-the-Wall gang, to which the real Butch Cassidy was a member of.
- Smug Snake: In the Western fantasy, Rabbit is irritatingly condescending to Pooh and Tigger whenever they meet.
- Token Evil Teammate: Rabbit is the most vindictive of the three law upholders. Justified in that the real-life Pinkertons weren't exactly the nicest people in the realm of law enforcement, to put it lightly.
- Toxic Friend Influence: Tigger reveals that he dragged Pooh into his criminal habitat and he (Tigger) stole the train. In the episode’s beginning, Tigger, in a purely Eddie Haskell-like moment, decides to play with the train set before it wanders out of Christopher Robin’s room.
- Train Job: The entire episode’s premise.
- Ungrateful Bastard: Even after joining forces with Tigger and Pooh in stopping the locomotive's rampage, Rabbit still points out that Tigger is still a train robber and that “none of this would have happened if it weren’t for him.”…until Pooh corrects him by saying that Tigger only meant to borrow the train and then things got out of control.
- Vehicular Assault: After Tigger rebuilds the locomotive, it goes off by itself for some nutty reason and attacks the town, demolishing the gallows and destroying Piglet’s office.
- Villain Protagonist: Pooh and Tigger are train robbers and the episode focuses mostly on them getting a redemption arc.
- Widely-Spaced Jail Bars: Parodied. Characters who aren't "in jail" walk right through the gaps in the bars multiple times, but those who are "in jail" only leave if the door is open, even if they don't necessarily leave that way.
