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.
Guest Stars: Tress MacNeille
as Other Characters and a Boy at Marty's party
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.