Diminutive attorney Bethany Horowitz asks for Alan’s help in a wrongful-death case she’s been pursuing against a tobacco company for seven years. The company, A.B. Curtis, has dragged out the case for so long that Bethany’s lead medical witness has died. Shirley is against fighting a tobacco company because nobody ever wins a case against them; but to her surprise, Sack gives the go-ahead. Alan asks a despondent Denny to aid him. During the deposition, Alan is thrown when he discovers that the defense attorney is Phoebe Prentice, a former lover. During questions they bicker until Bethany puts an end to it. Phoebe jumps on the fact that an autopsy was never performed on Mr. Rhodes, the victim.

When Alan and Denny confer on their plan of attack, Denny admits that he's depressed because he couldn’t perform in bed. He’s convinced he’s done for. Sack tells Alan he is to settle the tobacco case as soon as they make an offer. Denny asks Shirley to model her cheerleading outfit for him to see if it will arouse him. When she rejects this idea, he asks her to at least let him borrow the outfit. She runs him out of her office empty handed. Phoebe offers Alan one hundred and forty thousand as a settlement, and there is a definite sexual tension. Alan composes himself, and wonders what made her change: the Phoebe he knew would never defend a tobacco company. She tells him he’s changed too: his passion is gone, and his eyes look deadened. It stuns him, but he recovers enough to reject her offer.

In court Maureen Rhodes testifies about her father’s fifty-year battle with tobacco addiction. Phoebe establishes that cancer runs in the family, and that the houses he lived in were never tested for cancer-causing agents. During a break Denny and Alan argue about Denny’s erectile dysfunction. In anger Alan blurts out that it could be Denny’s “Mad Cow” disease. Denny is taken back, and now assumes that his penis has Alzheimer’s. Denny questions Alan, who admits that he once couldn't perform in bed... with Phoebe. He found out that she didn’t love him as much as he loved her, and after that he left her. Denny suggest that it’s not too late for them to rekindle their romance. Alan somberly tells him that she is happily married, with children.

An executive with A.B. Curtis testifies that his company spends millions on anti-smoking campaigns for kids. Jerry Espenson cross-examines, pointing out the huge number of people that smoking kills: the campaigns are actually crafted to get kids to smoke. As Phoebe works the case, Alan takes her in lovingly, and has a daydream set to a Barry Manilow song. The entire courtroom becomes a music video centered around the two of them dancing romantically. Later Alan explains to Denny that Phoebe hit on one of his greatest fears: that age will diminish his passion. Denny gives him a pep talk, saying that he is never dead in the courtroom.

Phoebe closes by reminding the jury that there is no proof smoking killed Mr. Rhodes. Alan rails against tobacco companies, giving the closing of his life. With so many deaths attributed to cigarettes, he cannot believe that they have not been outlawed. Tobacco companies have no conscience. He wonders how a company that kills a person every six seconds can keep getting richer and richer: twelve billion dollars last year alone; how can that be? He still has the passion, and Phoebe can’t suppress a bittersweet smile on once again seeing the man she fell in love with. The jury returns with a verdict for the plaintiff, and punitive damages against A.B. Curtis for two hundred and thirteen million dollars. Phoebe congratulates Alan, and they share a painful goodbye.

On the balcony Denny and Alan smoke their cigars, and share a drink. Alan tells Denny how grateful he his to have his friendship. Denny bemoans his condition until he discovers that Shirley has left him a gift: her cheerleading outfit. Denny starts to run off with it, but Alan demands a peek. It’s a two-piece; Alan talks a reluctant Denny into sharing it with him. Alan gets the skirt, and Denny the sweater. Clutching the clothing to their bodies, they each dance with their half of “Shirley” as Nat King Cole sings us out.