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Jenna Ryan is the main villainess from "Mr. Monk Goes to the Theater," episode 2.06 of Monk.
She was portrayed by Melissa George, who also played villainess Lauren Reed on Alias.
Jenna Ryan is an understudy looking to become a famous stage actress. Unfortunately, she has a psychotic side, as she was accused of attacking another actress during a play four years prior to the episode's events. In the episode, Jenna served as the understudy for Gail Fleming, Sharona's sister, and it was at that point that she colluded with her father in a twisted plan to achieve their goal.
Before their play began, Jenna laced an apple with peanut oil, knowing that Hal Duncan (whose character is supposed to bite an apple in the play) is allergic. As planned, Hal bites the apple and has an allergic fit just as Gail (in character) "kills" Hal's character with a prop knife. When the director calls for a doctor, Jenna's father rushed to Hal and posed as a doctor, but it was at that moment that he took the prop knife and stabbed Hal with a real knife, killing him. Their plan was to frame Gail and make it look like she really did kill him, with Gail's "motive" being that she and Hal had dated until Hal broke off the relationship.
Jenna ducked Sharona after their first meeting, but Sharona and Monk tracked her to a speed dating event, where Monk interrogates her. After the director witnessed Monk reciting Hal's lines as part of a recreation of the murder, he ends up cast in the play, which was an opportunity to get close to Jenna. During the play, Sharona finds a bottle of peanut oil and informs Monk, but Jenna caught Sharona with the bottle. Now knowing that both of them learned the truth, the psychotic villainess grabbed an actual knife (instead of a prop), looking to kill Monk. Seeing this, Sharona tackled Jenna and fought with her, tossing her into a shelf.
Jenna's father tended to his evil daughter, and it was there that Monk revealed their entire scheme. Jenna attempted to throw her father under the bus and claim that she wasn't involved, but to no avail. Both father and daughter were arrested.