Denny and Alan arrive at the Utah dude ranch for a vacation. They are dressed in bright and elaborate outfits for their outing. Alan does not look comfortable on the horse and Denny asks if he has ever rode one. Alan admits that he only rode a pony when he was young. While talking, they are approached by Melvin Palmer, the Texan attorney. He tells Denny that Alan and him go way back.
Back in Boston, Shirley visits Catherine Piper who is in jail again. Catherine tells her that she asked for Alan. Shirley says that he is out of the state and she will be handling her case. Catherine says that she is in jail because she was a victim of malpractice and took issue with her doctor. She says that she set her doctor's office on fire, which ended up blowing the man up. The doctor, Jeremy Marley, is still alive but is now pressing charges against her.
Catherine tells Shirley that Marley put her on a drug that caused a small heart attack that almost killed her. She later learned that Marley received kick backs from the drug companies. She then decided to take her revenge on Marley.
Shirley returns to the office and tells Carl about the case. She says that Catherine wants to plea temporary insanity. While walking down the hall, the team sees Jerry dressed up in a shepherdess outfit. Jerry tells them that his calendar told him that the day was Halloween.
Later, Jerry goes to his office and tells Katie that his smart phone dumbly informed him of the wrong date. Katie tells him that he looks great in the outfit. Jerry becomes concerned that his mistake might cost him his shot at making partner. Carl comes into the office and tells Jerry that the firm is a grown up place and that dressing up is a kid thing.
Later in court, Marley testifies that he returned to his office while it was burning. He says that he was treating Catherine for Kidney disease. Marley states that he gave her a drug that worked very well at first. He says that the side effects could not be anticipated, especially because is was a new drug.
Back in Utah, Denny approaches a woman, Irene, who is bending over. The man's husband, Ian, confronts him for trying to hit on his wife. He tells the owner of the ranch, Jensen, that he paid good money to have a good time. Later, Denny grabs Irene's butt causing him to be yelled at by Ian again.
Back in court, Catherine is placed on the stand to give her testimony. She tells the jury that she had a terrible heart attack. She says that the drug was considered safe by doctors that received a windfall profit every time they prescribed the drug. She says that the doctors and drug companies have enough money to pay for the law to look the other way when people get hurt.
At the ranch, Alan gets a cell call from the office just before the group is about to set off to go horse riding. Ian sees that Alan is bringing his work to the vacation and criticizes him. They get into a argument and Jensen shoots his gun in the air to quiet things down. Alan gets worked up again and the voices grow louder again. Jensen shoots his gun again to shut them up.
At the trial, a psychologist is called to the stand. He explains that Catherine probably went into a mild disassociate state where she was not capable of forming intent. The prosecutor asks how much he is being compensated for his testimony. The psychologist says ten grand.
Back in Utah, the group gallups along while Alan cautiously follows. They reach a campground and start a fire before it becomes dark.
Around the campfire, one of the ranch hands begins to sing a religious song. Instead of singing along, Alan decides to light a cigar. Ian becomes angry that he is being exposed to smoke. Alan tells the group that he wants to hear cowboy songs, not religious songs. Melvin asks for the guitar to sing a song.
Melvin sings a song about a couple of men playing dress up as cowboys. The group laughs as they realize that Melvin is poking fun at Denny and Alan's city slicker co