After finishing a game of checkers in the back of Mr. Chimp’s store (which Bill wins, like he ‘’always’’ does when he and Rupert play games...), Bill and Rupert stumble upon a Portal Door that leads to Gameland, home to sapient, life-sized pieces of all board games. Bill falls in with the undefeated Chessmen and Rupert with the team of all other games’ playing pieces as the two sides are preparing for the Ultimate Showdown of Ultimate Destiny. The two friends are looking forward to the game until they learn the stakes – control of the last bit of territory the various game pieces are allowed to call home. How can Rupert possibly get these two sides to make friends when he apparently can’t even convince his own friend to do what’s right...?
First major appearance of Bill, Rupert’s first trip to a Magical Land, and the first time Rupert convinces the antagonists to change their ways.
This episode provides examples of:
- And You Thought It Was a Game: It is, but the Chessmen’s definition of a “game” is very different from Bill’s...
- Assumed Win: Both sides are so sure the Chessmen will win that Bill doesn’t see any possibility of the others winning. Even Rupert’s so sure that he tries to stop the game rather than help the playing pieces fight.
- Book Ends: The episode begins and ends with Rupert and Bill playing checkers.
- Break His Heart to Save Him: Platonic version — for his plan to work, Bill has to convince everyone, including Rupert, that he’s betrayed his best friend.
- Cycle of Revenge: The King almost instantly demands a rematch as soon as he loses. The other playing pieces can’t wait to beat him again... Rupert easily sees where this is going.
- Defeating the Undefeatable: The plot.
- Determinator: Perhaps it goes with being a game piece, but neither side will consider giving up — to them, a forfeit is the same as a loss.
- Distressed Dude: Just like in a real chess game, the king can barely do anything — definitely not defend himself — and requires everyone to protect him.
- Et Tu, Brute?: Rupert’s thoroughly crushed when it seems Bill has betrayed him just so he can be on the winning side.
- Evil Cannot Comprehend Good: The King finds it perfectly natural that Bill would abandon his friend and help him push an army of innocent people out of their homes just to keep up a winning streak.
- False Reassurance: Bill chooses his words carefully when telling the King which side he’s chosen.“I’ve never lost a game before, and I’m not going to lose this one.”“I’ve always said there’s no point in playing unless you’re playing to win.”“Don’t worry — I don’t plan on losing.”
- Friend-or-Idol Decision: “Winner... or loser?!” With everyone taking it as a given the Chessmen will win, Bill has to choose if he cares more about winning or helping his friend.
- Friendly Rivalry: Unlike Rupert, Bill is excited when he finds out they’ll be playing against each other in what he thinks is just a particularly interesting game.
- Friendship-Straining Competition: It looks like the Big Game will be this for Rupert and Bill.
- Graceful Loser: Rupert truly doesn’t care that Bill always “beats” him. When he says, “Win or lose, I have fun playing,” he means it — he truly would rather lose than not play at all...
- Heel–Face Turn: Rupert’s description of his inevitable Pyrrhic Victory convinces the King to return the stolen territory to the other pieces and play “friendly matches” from now on without such high stakes.
- Honor Before Reason: The playing pieces are all but certain the Chessmen will still win, but they intend to fight anyway.
- I Let You Win: To his horror, Bill learns in the last scene that Rupert’s been letting him win all this time because he knew that would guarantee Bill would keep playing with him.
- Instant-Win Condition: Knock over the king, you win the chess game.
- Living Toys: Technically, games are a type of toy, so all the sapient pieces here qualify.
- My God, You Are Serious!: Bill initially assumes the other pieces’ claim that they’ll lose their homes if they lose the game is a joke and is horrified when the King casually confirms it’s true.
- Myopic Conqueror: The Chessmen clearly have no need nor use for the boards they conquer; they’re little more than trophies.
- No, You:King: We lost. WE LOST!Bill: You lost. I changed sides.
- O.O.C. Is Serious Business: It takes a lot to make Rupert Bear mad. This is one of those times.Bill: Rupert, are you hurt?!Rupert: No, Bill, I’m angry!
- Oh, My Gods!: Gamelanders use “My move!”
- Once More, with Clarity: Bill happily accepts and gloats over his victory in his checkers game against Rupert at the beginning. At the end, they’re playing checkers again, but this time, Bill’s paying attention and notices how Rupert deliberately let him win.
- Pass the Popcorn: Rupert tells Bill to stop trying to reason with the game pieces and sit down to watch the final game with him.
- Pyrrhic Victory: Rupert flexes his Guile Hero muscles when he talks the pieces out of fighting any longer by pointing out they’ll destroy themselves if they keep trying to beat each other.
- Ragtag Bunch of Misfits: The team consisting of all game pieces united against the Chessmen. They’re determined and willing to work together, but they’re a mess and lack any unified strategy.
- Reverse Psychology: Rupert gets the two sides to stop trying to destroy each other by encouraging them to fight to the death.
- Sore Loser: The King does not cope well with losing once after a stream of victories.
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"Stop Having Fun" Guys: The central theme. - Trap Door: The King throws Rupert and the tiddlywink out of his throne room with one of these.
- Unsportsmanlike Gloating: Bill does this constantly throughout the episode, repeatedly mentioning with pride how Rupert always loses to him. Turns out, there’s a very good reason it never bothers Rupert...
- Wham Line:Bill: You did it, Rupert! I couldn’t have played that one better myself! With moves like that, I don’t know why you’ve never beaten me.Rupert: Maybe because it’s fun having you come back for more, Bill...Bill: (horrified) You don’t mean...
- What Happened to the Mouse?: We never see how Rupert and Bill got back to Nutwood.
- You Meddling Kids:Rupert: That’s enough!King: Yes, enough of your meddling!
- Your Princess Is in Another Castle!: Hurray, the heroes have helped the good guys win, and the bad guys lost! Now everyone can go home, right...? WRONG! They want a rematch! *sigh* Is there a Warrior Therapist in the house...?
