Jay continues to review the films of 2000 from his beach decorated studio, as he is banned from all public beaches until he loses 20 pounds. Jay also receives an unexpected visit from Arnold Schwarzenegger.
Jay is hosting his 10th anniversary show live from Carnegie Hall where he showcases a number of movie clips from past episodes such as "Jurassic Park 2," "Every Which Way But Lucid," and the infamous "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.moreless
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, and 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 Doris claims to be Duke's love, Jay must get Duke and Miranda reunited before he marries the wrong woman.moreless
Franklin and Eleanor celebrate their 40th anniversary by going on vacation, but their plane crashes leaving Franklin and Eleanor marooned on an island. Back in New York, Margo and Jay find out about their disappearance and discover they have left Jay everything in the will. Jay decides to put the family fortune to use by cleaning up New York.moreless
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.''
Jay and Marty begin to feel a little big, so they enroll themseleves 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 after giving his latest movie a bad review.moreless
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.
When Jeremy Hawke's sister, Olivia Newton Hawke, visits New York, Jay meets her and is smitten with her. He puts his relationship with Alice on the line when she begins to feel left out, and Jay then must decide who he really loves.
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 reunite them.''
Jay's ratings are not doing so well and Duke is about to fire him, so Jay is feeling depressed. His mood improves when he meets a woman 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.moreless
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 modelled after him and does not leave him very pleased. Meanwhile, Jay tries to get along with his new pet dog.moreless
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.moreless
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, a parody of Time 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's boss, Duke, has just made a new invention, "PHILLIPSVISION" which alters movies to make them more likeable. 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.
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.
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. ''moreless
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 adoption. Jay mentions he is adopted and both start to think they are biological mother and son and must find more evidence.moreless
Jay celebrates his 1,000th 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.moreless
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 childrens idol Humphrey the Hippo.''
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.moreless
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 Rivera 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.moreless
Marty invites his dad, Jay, to career day at his school. Marty then 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.
When Jay has actress, Valerie Fox, on his show, they both fall in love with each other and get involved in a caring relationship. A relationship that may be threatened if Jay pans her performance in her new movie.