Film critic Jay Sherman falls in love with actress Valerie Fox. Jay's family and friends worry that Valerie is using him to get a good movie review. Does she truly care for him?
Marty invites his Jay to career day at his school where Marty develops a crush on a Cuban girl named Carmen. They go on a date but when Carmen decides to fly back to Cuba, Marty follows her and Jay must get his son back.
Jay is considered to be one of the most unpopular men on Earth (ranking even worse than Adolph Hitler) so Duke attempts to spruce up the show to get more people interested. When this doesn't work, Jay decides to soften his image by going on the "Geraldo Show" with his mother but Jay gets an even worse reputation when his mother embarrasses him to the point where he tells her to "shut up".
Jay, noticing everyone in New York has a fiancee except him, begins to feel unloved. Things change when he goes to review the movie, Indecent Proposal II, and falls in love with the projectionist screening the movie. They arrange a date at her house where she is revealed to have an obsession with Jay to the point where she kidnaps him and ties him to a bed holding him hostage.
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.
Jay celebrates his 1000th episode but the episode is less than successful. Ratings get worse so Jay seeks image consultant, Adolph Hitmaker, for advice. The advice is unsuccessful and Jay is fired. Jay gets a new job on a show which teaches English for cab drivers but Jay is unhappy so he decides to win himself another Pulitzer Prize.
Jay befriends his make-up lady Doris after they attend a musical adaptation of The Hunchback of Notre Dame, and thinks that she may be the mother who gave him up for adoption years ago.
When the studio catches fire during Jay's show, he collapses and must be rescued from the fire by Doris. When the news reports Jay's being rescued, he gets a reputation as being a wimp so he tries to prove his manliness by running in the New York marathon which tends to be more tiresome than it seems.
Jay is offered to write the screenplay for a new movie, Ghostchasers III, so he takes a break from his show to go to L.A. to write the new movie and experience Hollywood life but the movie producer isn't satisfied with Jay's script.
Jay's boss, Duke, has just made a new invention, "Phillips-o-Vision" which alters movies to make them more "like-able". Jay is disgusted with Duke's invention but when Duke is discovered to have a fatal disease, Jay must find a cure for Duke's ailment.
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.
