Anna and company go to the Kentucky Derby.

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Anna is invited to the Kentucky Derby and to a charity event. Anna and Howard start fighting over pictures of hats. On the plane Anna reads a book of lawyer jokes to Howard.

Howard is in charge of placing bets for the group. Anna's betting strategy is to bet on almost all the horses. They are told they can't take Sugar Pie to the Derby. Anna is very upset and says she cannot go to the track without Sugar Pie.

When things cool down they all, minus Sugar Pie, head off to the Kentucky Derby. Anna sees Larry King, Joey Fatone, and others. Afterwards, at the charity event Anna sees Kid Rock, Latoya Jackson, and Tammy Faye Bakker.

Howard meets a woman, Stacy, in the bar, but has to deliver drinks to Anna first. He convinces Anna to go meet Stacy and her mother. On the way back to the room, Anna and Howard have a huge fight. They eventually make up, however.