Pretty Persuasion is a 2005 American black comedy film directed by Marcos Siega, written by Skander Halim, and starring Evan Rachel Wood, James Woods, Ron Livingston, Elisabeth Harnois, and Jane Krakowski. Its plot follows a manipulative, sociopathic 15-year-old student at an elite Beverly Hills academy who accuses her drama teacher of sexual harassment.

Kimberly Joyce is a precocious, narcissistic, sociopathic high school student at Roxbury Academy, an elite preparatory school in Beverly Hills. She and her best friend Brittany take Randa, a new Muslim student who recently emigrated from the Middle East, under their wing. Kimberly's home life is troubled; her bigoted and disaffected father Hank, an electronics executive, shows little interest in her life, while her vapid stepmother, Kathy, constantly attempts to reprimand her for her coarse language and attitude. Kimberly dreams of becoming an actress, and obtains a coveted role as Anne Frank in the school play.

The school drama teacher, Percy Anderson, orders Kimberly and Randa to after-school detention one day for disrupting class, and forces Kimberly to write an essay reflecting on her transgression. Percy takes the essay home that evening and has his wife, Grace, read it aloud provocatively as a role play before the two engage in sex. After Brittany is publicly humiliated by Percy during an acting exercise, Kimberly devises a plan to accuse him of sexually harassing each of them. Unable to afford an attorney, Percy agrees to his friend Roger—a clueless high school law teacher who passed the bar —acting as his attorney. In court, Roger proposes that the accusations are in retaliation to Kimberly having been replaced in the school play after referring to her Jewish classmate Josh's lawyer father as a "money-grubbing shyster."

The case becomes a media sensation covered extensively by Emily Klein, a local lesbian reporter. Shortly after the trial begins, Kimberly has a sexual encounter with Emily. Kimberly then manipulates Josh with oral sex into convincing his father Larry, a renowned defense attorney, to defend Percy pro bono. When Larry cross examines Brittany, she confesses on the stand that she, Kimberly, and Randa fabricated the accusations. When Emily confronts her outside the courthouse, Kimberly reveals she filmed their sexual encounter, and uses it as blackmail to receive favorable press coverage.

Overwhelmed with the shame brought on her family by the false accusations, Randa shoots herself dead at school. Grace, now aware the essay Percy had her read was written by Kimberly, leaves him. In the storm of media coverage, Emily extolls Kimberly as a mere "victim" of society, and the ensuing press incites Hollywood producers to give Kimberly a bit part on a daytime soap opera.

When Brittany visits Kimberly at her house, Kimberly reveals she manipulated Josh into having his father defend Percy as she knew it would cause Brittany to buckle under pressure in court. When Brittany asks why, Kimberly explains that she devised the calculated plot to garner publicity for herself, as well as exact revenge against Brittany for having stolen her ex-boyfriend, Troy. Brittany lambasts her and leaves, vowing never to speak to her again. Kimberly turns on the television and sees herself on the episode of the soap opera. Switching through channels, she watches snippets of an interview with a school shooter and news footage of Randa's suicide before returning to the soap opera. As she watches herself onscreen, tears begin streaming down her face.

The plot primarily focuses on sexual harassment accusations within a school system, as well as the repercussions of one 15-year-old girl's actions. But the film also makes commentary on many other social issues in contemporary American culture as well, many of them being controversial. Some of the topics that are commented on include racism, ignorance, discrimination, gender identity, homosexuality, intolerance, immigration, teenage behavior, suicide, parenting, deceit, narcissism and fascination with celebrity status and the entertainment industry.

Director Marcos Siega, commenting on the film's thematic message, said: "At the end of the film there isn’t one overriding message I am trying to convey. I want the audience to walk away with their own opinions of what they have seen and their own feelings intact. The reality is that there are a lot of things wrong with our society and this film deals with some of those frustrations. I expect people’s reactions to be varied, and my only hope is that they walk away talking about it."