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.
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