Bored to Death Season 1 Episode 6
The Case of the Beautiful Blackmailer
Jonathan meets his new client at a diner. This man needs Jonathan to help get a video tape back from a woman, Sophia, who is blackmailing him with it. Sophia filmed him having sex with her and if he doesn’t pay her $1000 down plus $500 a week – she will show the tape to his wife.
Jonathan agrees to help this man. Somehow, not only is Ray now helping him, but George as well. George is very excited about the whole private eye gig. So much so that he ends up buying a bunch of private detective stuff – from a voice changer to night vision goggles.
That night, Jonathan sets up an encounter with the beautiful blackmailer at a hokey motel, while Ray and George wait in the car and smoke their brains out. It is great to see these two bonding over a piece pipe.
The beautiful blackmailer lives up to her name – and then some. Sophia seduces Jonathan and they do have some sexy time. She finds out his true identity and bribes him into paying her $500. Without his backup, Jonathan has no choice but to agree.
The three guys end up following Sophia and her brother back to her house. Once the brother leaves, Jonathan enters and informs her that he will go to the cops if she doesn’t give him back his money and all the video tapes. She agrees and admits it was for her brothers gambling debt.
The brother comes back and is about to kick some private eye ass, but thankfully this time Jonathan’s backups are paying attention. George and Ray burst in and help Jonathan flee. As they are about to get away, they end up crashing into a parked police car. The cops come out and arrest them for being under the influence.
As they are sitting on the side of the curb, George’s light bulb goes off and offers them both a job to write a comic for his magazine about the whole private eye gig. Being that they both aren’t really doing anything monetarily productive, they gladly accept.