The Loss of a Teardrop Diamond is a 2009 film by director Jodie Markell. The film is based on Tennessee Williams's long-forgotten 1957 screenplay. The film stars Bryce Dallas Howard in the leading role of Fisher Willow.
The film tells the story of heiress Fisher Willow (Bryce Dallas Howard). Fisher returns home from overseas to find that her father has become a hated man in Memphis as he had intentionally blown the southern half of his levee earlier that year, resulting in the deaths of two people and enormous property damage for anyone downstream. Fisher is to come out to society this season, but because of her father's reputation - and her inappropriate/wild behavior - she is unable to find a man willing to be her escort. She asks Jimmy (Chris Evans) to be her escort for the season. Jimmy is not her social equal - his father works on Fisher's land though he is a heavy drinker and is at risk of losing his job, and his mother was committed to an insane asylum and no longer recognizes her son - but she was always taken with him. Jimmy agrees to be her escort as she is willing to pay him and he could use the money to help his parents. Fisher arranges for him to be outfitted properly and promises that there are better places for Jimmy's mother.
For the season Fisher borrows $10,000 Teardrop Diamond earrings from her aunt. Fisher and Jimmy attend the first society party together where she causes a scene when she has the band play controversial music and dances in "flapper" fashion. Soon the entire party views her as a joke and laughs at her, insulting her father and the fact that she had to pay a man to be her escort. In response, Jimmy yells at everyone to shut up and helps Fisher to the car. Because of her behavior at the previous party, the only other social gathering that Fisher is invited to is a Halloween party in northern Memphis where no one knows of her father's previous actions. As he waits for Fisher to pick him up for the next party, Jimmy mentions to his father that Fisher had made it seem that she desired intimacy from him. Jimmy suggests that if he were to agree to be more than her escort, then it would certainly lead to marriage which meant a permanent job for his father and better care for his mother.
On the way to the Halloween gathering, Fisher asks Jimmy to stop up at the levee so she can look at the water. She rests her head on his shoulder before moving to kiss him. Jimmy, in spite of what he said to his father earlier, pulls back instead, causing Fisher to be hurt and embarrassed. When they arrive at the party, Fisher is so angry with Jimmy that she gets out of the car before it fully stopped. When she straightens out her clothes she realizes that one of her teardrop earrings had fallen off. Becoming frantic and somewhat hysterical - especially when Jimmy recognizes a girl outside, Vinnie, who was an old romantic interest of his - Fisher believes that the earring fell off when she walked away from the car and begins searching the ground for it. When she in unsuccessful she remembers that she had rested her head on Jimmy's shoulder earlier and asks him to check his pockets to see if the earring was there. Jimmy misunderstands and thinks that Fisher is accusing him of stealing the jewelry. He becomes furious, as his father was fired from a job once for stealing, and demands that she search his jacket. Fisher, confused as to why he is so angry, refuses causing Jimmy to go into the party and demand that he be searched down to the skin in order to clear his good name.
Fisher, needing to get away from all the commotion, goes upstairs where she meets Aunt Addie who is bedridden and unable to move her limbs due to a series of severe strokes. Addie says that she senses a kindred spirit in her, the same character that will not bend to the rules of society, and tells Fisher of a drug she used to use - Opium - before she was sick. She points to a bottle on the shelf and says it contains the last of her stash. She asks Fisher to give her all of the pills (since she is unable to move herself) so she can die and stop the pain. Fisher agrees but before she can go through with it she is interrupted by Vinnie telling her that Jimmy was searched and the earring was not on him. Fisher puts the bottle back on the counter and places her remaining earing next to it, promising Addie that she would be back to get her earring and would give her the rest of the Opiates then.
Fisher goes back downstairs to find everyone suspects her of "losing" her diamond on purpose so that she could blame Jimmy and not have to pay him for being her escort. Jimmy is still angry at Fisher for her accusation of theft and leaves her alone to go be with Vinnie. Soon, the people begin to play Post office, a kissing game. Jules, the hostess and friend of Fisher, gives her the highest card so that she can call Jimmy away from the other girl and kiss him herself. Fisher, growing increasingly distant hides in the bathroom where she finds a bottle of Addie's "medicine" which contains a small amount of Opium and drains it. Drifting through the party in a dreamy haze she reveals to everyone that, while overseas, she was actually at a mental institution. Still in a daze, Fisher misses when Jules asks who has the highest card and so Jimmy, who had the next highest, calls Vinnie to go out on the porch with him instead of Fisher. When she realizes that he chose Vinnie over herself, Fisher goes to the piano and plays a beautiful song, crying the whole time.
In the meantime, Jimmy and Vinnie have sex in a car outside. Vinnie tells Jimmy that she had an offer of marriage from a respectable man, but turned him down because she wasn't attracted to him like she was to Jimmy. Claiming that she didn't want any secrets between them, she brings him over to the back garden and digs in the ground to unearth the missing Teardrop Diamond. She had seen it on the ground while Fisher searched for it and had taken it. Vinnie says she knows where the other one is (she saw Fisher put it next to the bottle on the shelf upstairs) and that she and Jimmy could run away with the jewelry and start a life together. Jimmy refuses, telling her that just because they are poor, it doesn't mean they don't have any honor and she should return the earring to Fisher. Vinnie, angry, runs away with the earring.
Jimmy goes to look for Fisher and finds her in the car. She says she wants to go home, but Jimmy won't let her leave (he wants to find Vinnie and get the earring back). Jimmy pulls Fisher out of the car and there is a brief moment where they are close and Fisher looks longingly at him, before they are interrupted by Vinnie. She came back to return the earring to Fisher. Jimmy yells that they can leave now that she has her damn earring back, but before they go Fisher remembers her promise to Addie and runs back inside. After she leaves Jimmy thanks Vinnie for doing the right thing. Vinnie says that they will probably never see each other again as her only option now is to go marry the gentlemen who made her an offer earlier. They embrace, and Jimmy returns to the car to wait for Fisher. Fisher retrieves her other Teardrop Diamond and fulfills her promise to Addie, giving her the entire contents of the bottle and bidding her farewell. Addie tells her to go with God, Fisher replies that she is: she's leaving with Jimmy.
On the way home Fisher asks Jimmy to stop at the same levee they went to before the party so she can see the moon on the water. They stand on the levee together and Fisher tells him that she intends to fix her father's mistake and she can't run away anymore. She makes an offer to Jimmy. Fisher tells him that his mother will be taken care of, his father will always have a job, and while she knows that no one could ever love her, he could get used to her. She reaches up to touch his face, but he pulls away again. Heartbroken, Fisher turns to walk away, only to find that Jimmy had grabbed her hand - a silent agreement to her proposal. She turns back to him and once again rests her head on his shoulder.
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