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?
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.
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".
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 is given two tickets to a new play based on The Hunchback of Notre Dame. He tries to find a date but no woman will go with him so he goes with Doris instead. Surprisingly, Jay and Doris have a good time and their relationship eventually blossoms. One day Doris recalls she has a son she put up for adaption. Jay mentions he is adapted and both start to think they are biological mother and son and must find more evidence.
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.
Jay is asked by Duke to use his show to promote a new product, "Savvy Indian Chewing Tobacco". Jay doesn't want to promote tobacco so he tears up his contract and quits. He finds a new career in truck driving where he is praised by the other truckers but starts to realize the importance of his other job.
Eleanor is bored and feeling depressed with her life so he attempts to become an author and write a book. She writes a children's book called The Fat Little Pig which Jay learns is modeled after him which does not leave him very pleased. Meanwhile, Jay tries to get along with his new pet dog.
Jay's ratings are not doing very well and Duke is about to fire him so Jay is feeling depressed. His feelings become better when he meets a new girlfriend named Alice and her daughter Penny. Alice gives Jay tips on how to improve his show and her advice works. Jay wants to get to know Alice better but discovers she has a boyfriend whom she wants to reject but can't.
At Marty's slumber party, Jay is asked to tell his story in which he got caught up in the Gulf War. Jay tells how he was attending an Iraqi film festival and eventually was thrown in jail where he escaped and lead a troop of men across the desert.
Margo gets a new neighbor, Johnny Wrath, who is the lead singer in the rock group, "Nuns in a Blender". Margo falls in love with him but doesn't feel the relationship is right when she finds him with another girl. Meanwhile Alice tries to find a suitable preschool for Penny.
Jay and Marty begin to feel a little big so they enroll in a weight loss camp. Marty loses a remarkable amount of weight which makes him feel more self- confident but when he is placed as the star in a school play, he doesn't feel his skinny self is right for him. Meanwhile, Jay receives a death threat from Belgian actor Jean Paul Le Pope whose movie he panned.
When Jeremy Hawke's sister, Olivia Newton Hawke, visits New York, Jay meets her and is smitten with her which puts his relationship with Alice on the line when she begins to feel left out. So Jay then must decide who he really loves.
Franklin and Eleanor celebrate their 40th anniversary by going on vacation but the plane crashes and Franklin and Eleanor find themselves marooned on an island. Back in New York, Margo and Jay find out about their disappearance and discover they have willed Jay their entire fortune which Jay decides to put to use by cleaning up New York.
After Jay attends the Academy Awards ceremony, Siskel and Ebert have a fight on the plane ride home and split up. Jay sees his golden opportunity to be a partner to either Siskel or Ebert but feels they weren't right to be apart so he tries to get them reunited.
When Jay helps Marty become class president, Duke decides to have Jay help him become US President.
Alice's sister, Miranda, comes to visit them which Alice is not comfortable with. Miranda must find work in New York so she joins "Mattress in an Hour" delivering mattresses. When everybody attends a party held by Duke, Miranda falls in love with Duke but is shy because of a wrinkle. She runs out on Duke at midnight and Duke must find the woman who fits her slipper. When it turns out to be Doris, Jay must get Duke and Miranda reunited.
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.
