Jay Sherman meets actress Valerie Fox on his show and Jay falls in loves her. Although Jay's family and friends disapprove, and worry that Valerie is using him to get a good movie review... Jay finds out that this is the case later on the episode. Jay has to choose between love and the truth.
Marty, Jay Sherman's son, invites his dad to a career day at school where Marty studies. Marty falls in love with a Cuban girl named Carmen. After the date they arrange, Carmen has to fly back to Cuba and Marty follows after her. Jay must go to Cuba to get his son back, and finds out Carmen is the granddaughter of Cuba's president "Fidel Castro".
Duke (Jay's boss) attempts to fix up the show, when Jay is reviewed as the most unpopular man on Earth. When Duke's attempts fail, Jay promptly decides to go on the "Geraldo Show" with his mother to soften his image. but then Duke's second plan backfires and makes the situation even worse, when Jay talks back at his mother on live television. Jay is upset for what he's done to his mother, and tries to do his best to make his mother forgive him.
Jay feels unloved, he sees everyone in near him have either been married or engaged. He falls in love with a Movie Projectionist at the premier of "Indecent proposal 2", and later finds out she is insane.
Eleanor, Jay's mother, wants Margo, Jay's sister, to attend the annual debutantes' ball. Margo doesn't want to go to this ball, she believes it is sexist. Eleanor forces Margo to attend the ball by threatening to kill Margo's beloved horse. Jay decides to go with her to help his sister out. In another footnote Jay fights for his time spot against a children's show "Humphrey the Hippo", but what jay doesn't know is that the person under the costume has a secret crush on him.
After Jay's one thousandth show gets bad rattings, Jay decides to get an "image consultant". His show gets even worse ratings then before, Jay gets fired and has to get a new job at show where he teaches English to cab drivers. Jay decides, he wants to return to his old show by getting a Pulitzer Prize.
Jay gets two tickets for a play that is roughly based upon The Hunchback of Notre Dame, and Jay decides to look for a date to go see it with, he doesn't find anyone, so Jay decides to invite Doris. Strangely enough they find out they like each others companion because they had a great time together. Later Doris reminisces that she had given up a son for adoption and Jay Remembers he was adopted. And they both start to think they might be mother and son and they go in search for the truth.
The Studio where Jay works and Films at gets caught on fire, Jay gets trapped when some of the falling roof collapses on him, and Jay then is rescued by Doris. As the press finds out this, Jay is known as a wimp by the media. Jay then is determined not to be known as a wimp, he tries to go on, and complete, a New York marathon. Jay starts out ok, but then as he goes along he gets tired, and ends last on the race.
Jay gets offered to write a screen play edition to the sequel "Ghost chasers" called "Ghost chasers III", So Jay goes to LA to write it, while taking a hiatus from his show. While in LA Jay experiences the Hollywood lifestyle first handed, but then his screen play gets rejected by the movie's producers.
Duke, Jay's boss, has created a machine that makes movies more likable, which Duke calls "Phillipsvison". Jay does not like this machine. But then Duke fall ill to a fatal disease and its up to Jay to find some sort of cure for it.
When Marty fails on a school Field day event, he starts to feel down in the gutter, so Jay tries to cheer Marty up by getting him involved in learning to play a musical instrument, namely a guitar, and enrolls him in the schools talent show contest; While Jay is named by Them Magazine "the wittiest man alive". So Duke proposes to give everyone who doesn't laugh at Jay's show 100$ each. That turns out to be a bad idea.
In this episode, Duke wants to promote his new product "Savvy Indian Chewing Tobacco". So Duke asks Jay to promote his new product on Jay's show, Jay is reluctant to advertise Tobacco products on his show. So then Jay quits, and finds a new job as a truck driver, where his fellow "truckers" find Jay to be a great guy. Then Jay starts to remember the importance of his old job.
Jays mother "Eleanor " is depressed and bored, jay talks her into writing a book, Eleanor writes a children's book which she called "The Fat Little Pig", but jay then finds out its about his own life. In a subplot jay finds an abounded pup, which he names "Tiny".
On the Second season opener, Jay falls in love with his personal assistant Alice (voice of Park Overall), who happens to be a single mother, whose daughter is named Penny. Alice helps Jay improve his show by giving him useful tips that make his show lots better.
On this episode, Gene Siskel (a real life film critic) chooses Jay as Roger Ebert's replacement, following the pair's breakup. Siskel and Ebert supply their own voices, as do Gene Shalit and Rex Reed.
On this episode, Alice opposes Jay's budding romance with Jeremy's sister, when Jeremy sister, Olivia Newton Hawke, visits New York. Jay then has to decide who he really loves.
Margo's in heaven when she dates a rock star. The relationship then goes sour after Margo finds him with another girl. In a sub-plot, Alice tries to find a preschool for her daughter, Penny.
Jay becomes a casualty in the battle of the bulge, when he and his son attend a weight-loss camp. Jay doesn't lose any wait, while Marty does loose a ton of wait, which makes him allot more self confident, and gets him a role in the school play. This causes him to feel that his new found look to be right; Jay, in a sub plot is receiving death threats from an angry actor, which Jay gave a bad review of.
Duke gets the idea to run for president of the United States. So then Duke hires Jay as his speechwriter. Jay decides not to ask or tell the truth as he is Duke's speech writer for Presidential campaign. In a related sub plot, Marty becomes school president after Jay helped him out.
When Jay's son, Marty, throws a slumber party, Alice thinks its too "New Yorkie" for her daughter; So Jay decides to tell the tail when Jay was in the Golf War. Like the time when he was captured, then rescued and then wondered the desert for days without food or water.
Franklin and Eleanor (Jay's parents) celebrate their 40th anniversary by going off on a vacation. As they are on there way, their plane crashes on a deserted island. Margo and Jay find out about their parents sudden disappearance and discover their parent’s last will and testaments, which entitles Jay their entire fortune. Jay decides to put to use by cleaning up New York.
Miranda visits her sister Alice. This makes Alice feel uncomfortable. Miranda looks for work in New York. So she gets a job at "Mattress in an Hour". When everybody is invited to a party held by Duke, Miranda falls in love with him. But she gets shy because of a small wrinkle she has. She then runs out on Duke at midnight, so then Duke sets of to find the woman who fits her slipper. When Duke thinks its Doris, Jay has to find a way to get Duke and Miranda reunited.
Jay hosts his tenth anniversary show live from Carnegie Hall, where he shows movie clips from past episodes like "Rabbi P.I.", and many others. Jay's anniversary show at the Carnegie Hall gets held hostage by terrorists, who threaten to blow up the place with a bomb tied to Jay's waist.