Jack begins work in the mail room and discovers that if he sleeps with Kathy Geiss he could get his old job back. Liz is being interviewed by an adoption agency and is worried when the interviewer Bev, wants to see her workplace. Tracy’s computer game is a huge success and Jenna wants some compensation for her voice acting.

Liz takes some pills to help her sleep on a flight. Under the influence she thinks she meets Oprah Winfrey when in fact it is a young black girl. Meanwhile Jack is disturbed when his involvement in fake Olympic sports mean Kenneth loses respect for him. Jenna and Tracy argue over who has it tougher in America, white women or black men.

Liz’ friend Claire Harper (Jennifer Aniston) comes to town and begins stalking Jack. Despite Liz’ warnings he can’t avoid falling for her and ending up in night court. Meanwhile Kenneth is upset about new page uniforms being issued at NBC. To cheer him up Tracy tries to fix one of Kenneth’s other issues: that he never saw a proper finale to the NBC show Night Court. Tracy gathers three of the stars and tries to film a fitting finale.

Jack takes Liz to dine with eccentric agoraphobe millionaire Gavin Volure (Steve Martin). He asks Liz to come back and see him alone and she likes his strange situation. Unfortunately he has been lying and is actually under house arrest for fraud. He comes to NBC to try and convince Liz to come with him but he is caught by Tracy. Tracy had been using his sex dolls as decoys to try and avoid being murdered by his sons who he believes were after his money.

Don Geiss wakes from his coma and tells Jack that he intends to keep running GE until he dies. Depressed by this news Jack decides to head to Miami and drop Liz off in White Haven for her high school reunion. A storm forces Jack to go to the reunion and he decides he isn’t happy with his life. When he is mistaken for a Larry Braverman he decides to play the role. Liz meanwhile discovers that she isn’t the nerd no one remembers but the bitch they all hated. Back at NBC Tracy and Jenna combine to put Kenneth in his place for upstaging them.

Jack accidentally hits his mother Colleen with his car. He now has to take care of her over Christmas and is racked with fear that she will discover that he waited eight minutes before calling the paramedics. Meanwhile Liz isn’t going home for Christmas for the first time ever and so takes part in a Letters to Santa charity campaign. Jack decides that TGS will have a live Christmas special so that he can avoid spending time with his mother.

Liz’ obsession with babies leads her to ruffle the head of little person Stuart LaGrange. To get over the embarrassment she dates him and starts to like him until he realises how she really sees him. Jack hires a care worker (Salma Hayek) for his mother and ends up falling in love with her after detecting a growth in his testicle. Jenna wants to star in a new movie about Janis Joplin but a rival production starring Julia Roberts prevents her.

It’s almost time for Liz’ special vacation and the crew are coming down with the flu. When Liz discovers that there is only enough flu vaccine for the important people she refuses to take it and enjoys her new popularity with the crew. Tracy and Jenna decide to do something nice for the crew to make themselves look good, but they are so useless that they fail at all of their attempts. Jack wants to take Elisa out on a date but she works every day including with Mr Templeton, who suffers from dementia. Jack takes her out and brings Mr Templeton with them.

Jack asks Liz to accompany him on his corporate retreat because he is worried about how he will be perceived after leaving GE at the end of last season. Once there though he is welcomed back by the elite and Liz is left out. When Jack asks Liz to behave more appropriately she ends their friendship. But when Jack embarrasses himself, she goes to great lengths to cover up for him. Back at 30 Rockefeller Centre Tracy Jordan is diagnosed with diabetes and Kenneth is desperate to get him to eat more healthily. Jenna tries to method act like Janis Joplin and when Frank messes with her she ends up sleeping with him. The next day he wants to keep it quiet but her ego won’t let him.

Elisa’s mother doesn’t like Jack because he reminds her of the evil Generalissimo on her telenovela. So Jack buys the show and tries to write the Generalissimo out of it. But after a confrontation with the actor they agree that the Generalissimo will make Elisa’s mother like Jack by changing his behaviour on screen. Meanwhile Liz falls for her neighbour and uses the Generalissimo’s evil tactics to seduce him. At NBC Jack has hired some interns who are out of work investment bankers. Tracy is desperate to keep his youthful reputation alive and so keeps partying with them.

Jack wants to take Elisa to a fancy restaurant for Valentines Day so that they can eat a really expensive desert. But she insists they go to church and that Jack go to confession. Once in there Jack upsets the priest and Elisa breaks things off. But their mutual love of McFlurry’s bring them back together. Meanwhile Liz’ first date with Dr Baird goes from bad to worse as he suffers multiple family crises after Liz suffers multiple embarrassments. Finally Kenneth falls for a new blind employee but can’t speak to her so Tracy steps in to do the talking for him.

Tracy is a guest on Larry King Live as the Asian financial markets go into a heavy sell-off. Tracy’s mad advice creates panic at GE and on the streets of New York. Liz leaves her phone in a cab and the driver wants money to return it. Kenneth is the only one from NBC who will help her. Finally Jack tells Elisa that he loves her and asks her to stay with him instead of going home to Puerto Rico. The crisis forces him to rethink his priorities and he proposes to her but she ends up going home feeling that the crisis had forced him into a rash decision.

While watching Harry and the Hendersons Jack and Frank bond over their absent fathers. The next day Jack offers Frank the chance to complete his law degree. Frank is happy but his mother Mrs Rossitano warns Jack off because Frank’s family were lawyers for the mafia. Channelling George Henderson, Jack sends Frank back to the writers’ room. Liz meets a pregnant girl while buying doughnuts and befriends her in case she can use this as a shortcut to adoption. Kenneth discovers that Tracy has never had a birthday and decides to turn Jenna’s birthday into a joint party.

Liz is called to jury duty and leaves no one in charge at TGS. Jenna is exhausted because she is filming her Janis Joplin movie at night and so takes experimental pills from Dr Spaceman. Tracy realises he can say whatever he likes on television and pay off the regulators afterwards. Jack grabs the TGS writers and works with them to come up with a name for his pocket microwave.

Liz discovers that Drew lives in a bubble because he is so good looking. He gets great treatment wherever he goes and doesn’t realise that he is bad at everything including being a doctor who doesn’t know the Heimlich manoeuvre. Jack has to renegotiate Tracy’s contract but when he points out that Tracy doesn’t need to work, he quits. But Jack realises that Tracy’s weakness is Kenneth (and all that he does for him) and lures him back to work at TGS. Jenna agrees to cut her hair for charity but it is really for publicity.

Jack is turning 50 and his mother sends him some home movies. In one of them the 10 year old Jack vomits from excitement about a present he receives. Despite his success Jack wants to feel that excitement again. Meanwhile Dennis returns claiming to be a sex addict and needing to apologise to Liz. She then discovers that he slept with Jenna but she is determined that it won’t affect their friendship. But it does and she lets Jenna fall and hurts her leg. To make it up to her she allows Jenna to tell the writers about a sex line commercial she did. The ensuing footage is so embarrassing that Jack throws up out of sheer happiness.

NBC is cutting back everywhere. They bring in a consultancy firm who begin slashing Liz’ budget. Liz in inspired by one of the women Jack has to sack. She sleeps with Brad Hollster (the consultant) in exchange for not laying off any of her staff. Only he doesn’t know that. Meanwhile Kenneth becomes Jack’s assistant after Jonathan is laid off. He asks Tracy to feed his pet bird but not to go into his bedroom. Tracy and Jenna assume Kenneth must be a serial killer and accidentally kill his bird.

When Jenna is accidentally announced as dead, Jack leaps on the opportunity to promote her Janis Joplin movie. Liz is struggling to know what to do at home as she serves her sexual harassment suspension. A group of rich women who live for leisure take her in and she soon sees the benefits of not working.

Elisa returns but admits she doesn’t know if she should marry Jack because of a dark secret. It turns out she killed her first husband when he cheated on her. Jack goes out with Tracy to see if he can resist temptation but when he discovers Elisa followed him they break up. Jenna meets a cute paramedic and keeps poisoning Kenneth to try and meet him again. Tracy has to buy his wife a twentieth anniversary present.

Jack’s mother is in town and it’s the 35th anniversary of when Jack’s father left them. Colleen has brought her boyfriend Paul with her and Jack doesn’t like him. Tracy demands that Liz treat him like everyone else but they both dislike the results of true equality. Jenna adopts a wild monkey with disastrous results.

Liz encourages Jack to seek out his father. He gets Len on the case and discovers that there are three men who could be his father. Jack and Liz set up a fake contest and invite the three men to come to New York. Once there it becomes clear that Jack’s father is liberal professor Milton Green. He is thrilled to have Jack as a son because he needs a kidney. Tracy introduces everyone to his illegitimate son Donald who is clearly not his son and scamming him. A catchphrase which Liz wrote for Jenna suddenly takes off and she is invited to pose for Time Out as the funniest women in New York. Liz is jealous and joins her for the shoot.

Jack isn’t a match to give Milton his kidney. So he gathers a group of pop stars to sing at a charity concert called “Kidney Now.” Liz and Jenna go on “The Vontella Show” and Liz ends up giving advice to women using her “Dealbreaker” catchphrase. Following Jack’s advice she begins to take advantage of her notoriety. But her bad advice gets her in trouble with her male friends. Tracy is asked to speak at his old high school but refuses. Kenneth helps him work through his painful memories of dropping out and he gives a speech.