Roseanne goes into labor on her favorite holiday (Halloween) and gives birth on a pain-medication-induced psychedelic trip.

Roseanne and Jackie's shopping trip turns into a road trip when they pick up a hitchhiking teenage girl. Dan gives Mark relationship advice that severely backfires.

Mark tries to cheer up a glum Becky by inviting the family over for a surprise get-together. As the night goes on, Becky's mood only worsens which prompts Roseanne to pull her aside for a heart-to-heart talk. Becky admits she feels like she missed her chance to go to college and become a therapist or an EMT. Becky even admits to having second thoughts about her marriage to Mark.

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.

Dan is at a crossroads when a promising new construction job opens up that could make him and his old crew a lot of money. He struggles with whether to continue his job at the garage or to strike while the iron is hot on the construction job. Meanwhile, Jackie reluctantly starts using the internet on her new computer and is amazed how much she likes it. She becomes so obsessed a concerned David has to intervene.

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.

David moves out when he gets a job at a strange local theme park. Soon, David is transformed into "Hans the Hare", a hyperactive and perky park employee. Roseanne steps into action in order to get the real David back.

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

Dan is rushed to the hospital after having a heart attack and Roseanne tries to pull herself together while she's stuck in the waiting room.

Dan returns home from the hospital but Roseanne finds out he's not sticking to the doctor's orders.

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.

After finding out they won the Illinois State Lottery, the Conners and family imagine how to spend their new-found wealth. Kathleen Sullivan and Robin Leach interview Dan and Roseanne in their home. Throwing a party in their home proves that people really do come out of the woodwork to help celebrate wealth. Dan and Roseanne vow to not let money change who they are.

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

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.

Roseanne misses Dan and tries to prepare the home for his return. Bev visits with Nana Mary to talk about her life and makes a startling discovery.

Dan regretfully packs his bags and prepares to leave home for good. Roseanne deals with her sorrows by driving aimlessly around Lanford.

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.

Dan is unnerved by rumors of Roseanne and Edgar so he makes a surprise trip to see her. They make some tentative steps to putting the pieces of their marriage back together. Their peace is interrupted when a frantic call comes in from Jackie: Darlene has unexpectedly been rushed to the hospital.

Dan's estranged mother heads straight to Lanford for a visit after she's released from the hospital. However, Dan suspects she's far from cured and is afraid she's trying to kill him.

The Conners welcome baby Harris Conner-Healy home. Roseanne is delighted Darlene wants to live at home and work on her parenting skills. The family talks about their lives after winning the lottery and are glad they have all come out of it stronger people. Over a pizza dinner, Roseanne suggests they say grace to thank God that Harris survived and the family is together again.

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.