Fred tells Jackie that he doesn't want D.J. to visit their house so much, because he gets weirder every time he comes over. To protect Fred, Jackie tells Roseanne that she is the one who has a problem with D.J. constantly being at her house, which infuriates Roseanne. Dan tricks Darlene into coming home for the weekend and tries to make the girls stop bickering for their mother's sake. D.J. expresses a strange new fascination with eating cardboard.

Nana Mary visits Roseanne and Jackie at Jackie's house, and brings a box of their childhood belongings. Among them was a doll that Jackie thought was lost forever, and causes a huge fight when Jackie realizes that Roseanne was the one who hid it from her all those years ago out of jealousy. Dan has a poker game at the house, and Roseanne convinces him to invite Leon and Scott, but is worried that they will spend the whole night nagging each other like housewives. The men have a spirited discussion about how blacks, gays, and poor white men are looked upon in this country.

Magic, wonder, and whimsy surround the Conner family on their tour of Disney World. The only person not amused is Darlene...until she meets Winnie the Pooh.

Darlene and David get married. Dan suffers a heart attack during the ceremony.

After leaving Dan for not taking better care of himself, Roseanne goes on a "spiritual odyssey", imagining herself and Dan as Ann and Donald from "That Girl", Jeannie and Major Nelson from "I Dream of Jeannie", and Mary and Lou from "The Mary Tylor Moore Show". The family tries console Dan, and encourage Roseanne to reconcile with her heart-broken husband. Jackie discovers that they won the Illinois State Lottery worth 108 million dollars.

The Conners are invited to a wealthy Cape Cod estate, where Roseanne butts heads with the "old money" set.

Roseanne battles a group terrorists holding her family and a foreign diplomat hostage on a train to Washington D.C.

Thanksgiving for the Conners starts on a sour note with the news Dan won't be able to make it home for the holiday. However, Roseanne is thrilled she can afford to have the meal catered instead of spending an entire day in the kitchen. Family squabbles combined with a shocking revelation by Bev nearly ruins the evening. The family must contend with the fact that money does not necessarily buy happiness.

When Roseanne falls into a deep depression and locks herself in the bedroom, family and friends try their hardest to pick her spirits back up. When their efforts prove fruitless, they stage an intervention to rouse a lethargic Roseanne out of bed.

Family and friends gather at the Conner house to celebrate baby Harris' Homecoming and everyone takes a turn chatting with the new addition to the family. Mark and Becky have some exciting news, as do Leon and his husband Scott. During dinner, Roseanne takes time to reflect on each member of her family and reveals she has been writing a book; everything we see is Roseanne's altered version of actual events. Roseanne reveals the true story and admits she changed whatever details she didn't like about her life and the people in it. In truth, the Conners never won the lottery; it was all a fantasy Roseanne created in order to cope with a devastating reality. In the final moments, Roseanne sits alone in her basement writing room. She goes upstairs, passing through the old kitchen and the old living room. Roseanne sits on the old couch with the classic afghan on the back and silently takes in the warmth and comfort of the family home as the lights slowly fade.