At a chance encounter at Community General, Jack meets an old friend of his by the name of Sandy Hoyle. Noticing some injuries to her arms, he and Mark grow concerned. This leads to Jack stopping by Sandy's place and discovering she is a call girl. She assures Jack that she won't be in the game for much longer, as she is going to persuade three of her clients to donate a very generous retirement fund for her with the help of an audiotape.
The astute among you may be reading between the lines and seeing this retirement fund as blackmail, and may also expect that this does not end well for Sandy. You would be correct, as Mark finds Sandy dead in her apartment of an apparent heroin overdose. With time on his hands via a vacation "requested" by Community General's ethics board, he sets out to find the killer with Jack and Amanda, all the while searching for a backup Sandy left in the head of someone only known by "Lily"...
"Lily" displays symptoms of the following tropes:
- And Starring: Gerald McRaney gets a "Special Guest Star" Credit, while Romy Walthall gets a credit with Sandy's name.
- Blackmail: Sandy picks out three of her most notable clients for this.
- Charles Simmons is a guru to the stars, so his reputation would be on the line.
- Michael Davis is planning to take his construction business public, and the SEC generally looks down on a company owner cooking the books to cover using petty cash to pay a call girl.
- Joseph Talbot not only owns the Herald Express newspaper, but is planning a gubernatorial run, and of course, politicians and call girls do not mix.
- Blackmail Backfire: Sandy falls victim to this.
- "Blackmail" Is Such an Ugly Word: When Michael says Sandy is blackmailing him, she says she prefers to think of it as Michael and the others "contributing to her retirement fund".
- Chekhov's Gunman: Detective Andy Ruggio is first introduced bursting into the crime scene on Mark, and is later revealed to be the murderer.
- Church of Happyology: With celebrity connections and focus on testing with odd machines, it becomes clear the Center for Psychic Wellness is based on these guys.
- Cigar Chomper: Mark finds a match burned near to the end under Sandy's body and determines her killer is a cigar smoker.
- Dirty Cop: For the past year, Vice Detective Ruggio has been giving Sandy protection.
- Dirty Coward; Sandy states in her audiotape that while she's blackmailing Simmons, Davis, and Talbot, she doesn't think any of them would have the guts to kill her. Andy Ruggio, on the other hand...
- Drink-Based Characterization: Each of Sandy's blackmail victims is having a different drink with her by her fireplace.
- Charles is drinking Scotch on the rocks, an older man with ties to the famous and wealthy.
- Michael is drinking a martini, a business man whose company is about to go on the public stock market.
- Joseph drinks a red wine, refined for a man of the press going into politics.
- Exact Words: Sandy says she had a copy of her blackmail tape in "Lily's head". Everyone naturally thinks it means a person (originally believed to be another hooker, but turns out to be her mother) having memorized the tape. She really means she hid it in the bathroom (aka, the "head") of Lily, the boat she bought her mother.
- High-Class Call Girl:
- Sandy fancies works- er, worked - as one.
- As Mark visits Madame Elaine, she sets him in a room with one of her girls, Bambi.
- Killer Cop: Detective Ruggio turns out to be the killer.
- Make It Look Like an Accident: Well, "Make It Look Like A Heroin Overdose", really. Not that the main gang buy it anyway.
- Outliving One's Offspring: After Sandy's death, one of the people the investigaters talk to is Sandy's mother, Lily.
