Eleanor is determined to have her daughter, Margo, attend the annual debutantes ball as it is a tradition in her family. When Margo is reluctantly forced into it, Jay decides to accompany her. Meanwhile, Jay competes in his time slot against children's idol Humphrey the Hippo.

After Marty fails to win an event at his school field day, he is feeling very low so Jay tries to improve his self-confidence by getting him interested in playing guitar and putting him in the school talent show. Meanwhile, Them Magazine names Jay "the wittiest man alive" so Duke offers to pay everyone who doesn't laugh at Jay's show $100 which doesn't go over very well.

After Jay attends the Academy Awards, Gene Siskel and Roger Ebert break up and each rope Jay to be their new partner.

Jay is hosting his 10th anniversary show held at Carnegie Hall where he showcases a number of movie clips from old episodes such as Jurassic Park 2, Every Which Way but Lucid, and Rabbi P.I. The show is later held hostage by a number of terrorists who threaten to blow the place up with a bomb tied to Jay's waist. Fortunately, everybody is eventually rescued by Milton Berle.