When a clown visits Tarrytown Airport, Jay Jay, Tracy and Herky play a new game, Funny Face, where one has to make the other laugh by making a funny face. But since Jay Jay will do anything to win, he fails to follow Brenda's wise advice and as a result, his face gets stuck.
One day, Jay Jay and Tracy are playing Jump Jet, and Jay Jay is about to jump over six bales of hay in a row, his best was five. Jay Jay jumps and makes it, and Tracy thinks he'll do anything to win a game. Jay Jay says when he plays a game, he always tries to win. As they talk, a clown walks up to them and asks where he can find Old Oscar. Obliviously, Jay Jay tells him he lives in the barn, and it's not until he leaves when they realize who they've talked to. Wondering why a clown is at the airport, they go off to find out.
At Oscar's barn, Jay Jay and Tracy are introduced to the clown, Flippo, an old friend of Oscar's, which explains why he is at the airport. They used to be in the circus years ago, and Flippo is going to a Clown Convention at Tarrytown Hall. Jay Jay wonders what they do there, and Flippo explains they have all kinds of fun, one of the events is a Funny Face Contest, where one has to sneak up on someone and make a funny face; if the other person laughs, they receive a point, and the one with the most points wins.
Later after Flippo had left, Jay Jay and Tracy explain the rules of the Funny Face game to Herky. First, they have to split up and hide, and then they have to sneak up on each other and surprise each other in return. Jay Jay declares the Funny Face contest to begin, and everyone splits up. First Jay Jay surprises Tracy, then Herky surprises Jay Jay, and finally both Jay Jay and Tracy surprise Herky. Then the kids sing Funny Face.
Some time later, when the kids return to the airport, Jay Jay is winning and only needs one more point to win, but the game is stopped when Brenda calls Jay Jay to the hangar to get a new coat of airplane polish. Jay Jay is annoyed, but Tracy and Herky decide to wait until he comes back.
In the hangar, Brenda is polishing Jay Jay, who normally loves this, but today is so impatient that he can't stop squirming to get back to the Funny Face game. When she finishes, she gives him a warning to not make any funny faces before the polish dries. Jay Jay agrees and exits, Brenda hoping he'd remember. However, since Jay Jay is so anxious to win, he forgets this statement.
Back outside, Jay Jay notices Tracy and Herky talking to each other, oblivious to him here. This gives Jay Jay the cue to sneak up on them and surprise them to win the game, and since he does anything to win, he does just that. Tracy declares Jay Jay the winner and that he made the goofiest face ever. But when Jay Jay tries to let his face return to normal, he suddenly can't, much to the shock of the others. This was what Brenda warned him about: he made a funny face while his polish was still wet, and now it dried suddenly, resulting in his face to get stuck.
Later, Jay Jay tells Tracy and Herky that he told Brenda the problem, but she had to go into town to get polish remover and he has to be stuck this way until returns, and his face is starting to hurt a little. Tracy and Herky suddenly start laughing, and Jay Jay is confused. Tracy explains that even though his face is stiff, it's the funniest face of all which made him win. Jay Jay is cheered up by this, and promises from then on to not do anything to win a game, and decides to show his face to everyone to get some fun out of it.
Jay Jay uses his winning face to surprise Oscar and later Savannah, before the trio sings a reprise of the Funny Face song. As the episode ends, the narrator says that Brenda was able to get Jay Jay's face back to normal, but everyone will remember his funny face.
Flippo: (walks up) Excuse me, can you tell me where I could find Oscar?
Jay Jay: (obliviously) Sure. He lives in the barn in the back.
Brenda: (finished with Jay Jay's polishing) Well, I think I'm done. But, if you don't shine brightly, it's not my fault this time!
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