I remember the princess being kidnapped by an evil witch or queen who didn't like to smile. The boy and conductor went on a journey on the conductor's train to find out where she is and rescue her. Eventually they find her, I think and they managed to convince the evil queen or witch that smiling was good and she laughs.
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Can you remember when you watched this and anything else that happens? If so you can edit that into your question.– TheLethalCarrot ♦Nov 11, 2019 at 15:36
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1Sounds like "Jim Knopf". In what language did you watch this? Could not find an english wiki entry because this is a german/french series, not sure if this was synchronized to english... But without further information i can not say for sure...– kl78Nov 11, 2019 at 15:41
1 Answer
This sounds extremely close the german classic book Jim Button and Luke the Engine driver which was adapted into a cartoon series in 1998 (pictures here). It is about the boy Jim Button who grows up on a small island without knowing his real parents with the engine driver Luke being his best friend. They embark from their island on board of their train engine (turned into a boat by emptying the tank) to relieve concerns of overpopulation and come across a china-inspired country called Mandala where Princess Li Si was kidnapped by a (very witch-like) Dragon named Ms. Grindtooth who intends to use children to learn to laugh from them. In the end they do manage to defeat her which triggers a transformation into a "Golden Dragon of Wisdom" making her benevolent.