In the 1950s, Lanny Morris (Bacon) and Vince Collins (Firth) are the most popular comedy duo in the States, until the mysterious death of a college student Maureen O'Flaherty (Blanchard) in their hotel room prompts the two to end their collaboration and disappear from the public eye. Fifteen years later, journalist Karen O'Connor (Lohman) tries to find out what happened that night.
This film provides examples of:
- Alice Allusion: the appropriately named Alice, a young singer Vince uses to blackmail Karen, appears in an Alice in Wonderland dress, performs Jefferson Airplane's "White Rabbit", and is associated with psychedelic drug use.
- And That Little Girl Was Me: Karen tells the story of a little girl with polio who was able to get treatment thanks to money raised during a telethon in the 1950s. It turns out it's her.
- The Butler Did It: Lanny believes Vince killed Maureen and Vince thinks Lanny is the murderer. It turns out that Reuben, Lanny and Vince's valet and "fix-it man", strangled her to keep her from blackmailing Lanny and Vince with the audio she had recorded during their sexual encounter. The reveal hurt the movie; as one critic noted the ending was "straight out of the big book of mystery clichés".
- Closet Gay: Vince. More specifically, Closet Bisexual.
- Coitus Uninterruptus: Lanny measures his flings by how they react to being seen naked by hotel staff, although usually not during but immediately after sex.
- Depraved Bisexual: Vince could arguably fit this trope given his treatment of Karen.
- Determinator: Karen will stop at nothing to learn the truth behind the Lanny and Vince's breakup. Not even being raped and threatened with sexually humiliating blackmail will stop her from achieving her goal.
- Double Standard: Rape, Female on Female: Vince drugs Karen and then arranges for Alice, an aspiring young singer he's training (and who, yes, dresses like Alice from Alice In Wonderland), to have sex with Karen while Karen is stoned out of her mind and unable to think clearly. When Karen wakes up in the morning, completely naked and humiliated, even more so when Vince shows off the pictures of her drug induced tryst (which he intends to use to blackmail her), Vince has the nerve to insinuate that it was no big deal - he even jokes about how Alice couldn't get her pregnant! The film doesn't really focus on it much in the final half but Karen is clearly not happy about what happened.
- Forced Out of the Closet: Maureen blackmails Lanny by threatening to publish audio recordings that would reveal Vince's bisexuality, thus ending their joint career. This leads to her murder.
- Girl-on-Girl Is Hot: The movie featured a drug-induced lesbian sex scene between Karen and Alice, with Karen arguably a victim of the Double Standard: Rape, Female on Female trope.
- Incompatible Orientation: This could be one way to read Lanny's rejection of Vince's sexual advance. However, the scene is ambiguous in this regard.
- Introduction by Hookup: Karen and Lanny have sex shortly after meeting, while Karen is in New York and using her best friend's name. Later they meet for real when Vince meets with Lanny to work on Karen's book, which doesn't go well.
- Ms. Fanservice: At least three counting Karen herself, some of them more shameless than others.
- My Eyes Are Up Here: Inverted when Lanny tells a female audience member "I think you have the most beautiful eyes I have ever seen. Now you notice I say 'I think you've got the most beautiful eyes I've ever seen'; that's because I haven't actually seen them yet. I've been too busy staring at your cans."
- No Celebrities Were Harmed: Lanny and Vince's double act seems very similar Martin and Lewis, with them even hosting telethons, much like Jerry Lewis became famous for doing later in his solo career.
- Out of the Closet, Into the Fire: Vince's suicide has elements of this, though not exactly in the right order: it occurs after Karen begins looking into Maureen's recorded tapes, which eventually leads to her learning about Vince's bisexuality.
- Three-Way Sex: the catalyst for the film's plot is a threesome gone wrong.
- Unreliable Narrator: Karen is anonymously sent manuscripts for chapters of Lanny's memoir, his voiceover reading of such making up the narration for the film's flashbacks to the 1950s. However, the reliability of these manuscripts is later brought into question.