Ep 6. The Case of the Beautiful Blackmailer

The Case of the Beautiful Blackmailer is an episode from the first season of the comedy-drama television series Bored to Death. The series revolves around Jonathan Ames, a struggling writer in Brooklyn, who decides to become an unlicensed private detective after a break-up and some traumatic life experiences.

In this episode, Jonathan, played by Jason Schwartzman, is hired by a beautiful woman named Jennifer (Olivia Thirlby) to investigate a blackmailing threat against her. Jennifer visits Jonathan's apartment, where he lives with his best friend, Ray Hueston (Zach Galifianakis), and their comic book artist friend, George Christopher (Ted Danson). Jennifer tells Jonathan that someone has been blackmailing her with a video of her having sex with a married man and demanding ten thousand dollars to keep the video a secret. She claims that she did not know the man was married, and that she has no idea who is behind the blackmailing.

Jonathan agrees to take on the case, and starts investigating by visiting the restaurant where Jennifer met the married man, and by tracking down the source of the blackmail mails. Meanwhile, Ray, who is struggling with his own problems, is visited by a former college friend, Spencer (John Hodgman), who invites him to a party where he is supposed to meet his idol, Jonathan Ames, the writer. Ray, who is envious of Jonathan's success as a writer, reluctantly agrees to go to the party with Spencer, hoping to impress Jonathan with his own literary talent.

As Jonathan digs deeper into the case of the beautiful blackmailer, he discovers some surprising connections between the characters involved. He meets the husband of Jennifer's lover, who turns out to be a famous artist, and he meets a mysterious woman who seems to know more about the blackmail than she is letting on. As he gets closer to unveiling the truth, he is threatened by a shadowy figure who warns him to back off.

Meanwhile, Ray and Spencer attend the party, where Ray drinks too much and embarrasses himself in front of his idol, Jonathan. He also discovers that Spencer is not the successful businessman he claimed to be, and that he is actually a drug dealer, who offers Ray some cocaine. Ray declines, but Spencer insists, and the two end up getting high and causing a scene at the party.

Back at his apartment, Jonathan confronts the blackmailer, who turns out to be a surprising figure with a hidden agenda. He also discovers that Jennifer has been lying to him about certain things, and that she is not as innocent as she claims to be. In the end, Jonathan solves the case and gets paid, but he also realizes that his life as a detective is not as glamorous or rewarding as he thought it would be.

The Case of the Beautiful Blackmailer is a funny, quirky and suspenseful episode, with great performances from the main cast, especially Jason Schwartzman, who brings a charming and neurotic energy to the role of Jonathan Ames. The episode deals with themes of love, betrayal, identity, and ambition, and it offers a fresh and distinctive take on the classic film noir detective story.