I found Umney's Last Case particularly unsettleing.
(SPOILER WARNING: I'm going to be describing the whole events of this episode, you really shouldn't read ahead unless you've already seen it.)
In Umney's Last Cast 1938 private eye Clyde Umney finds his world turned inside out when he meets his creator, 2005 author Sam Landry, who tells Clyde he is in fact a ficticious character living in a fictional world. As it turns out, Sam's young son drowned in a pool, and he was unable to comfert his grieving wife. Now he wants to switch places, so that he, Sam, will live in the ficticous 1938 and Clyde will live in the real-world 2005 with Sam's wife, Linda Landry. Sam believes Clyde can help Linda better than he ever could. Clyde is then transported by Sam to the real world at the Landry home. After Linda's initial shock of seeing Sam's character brought to life, she is happy and excited by the charming Clyde, and it seems things will be O.K. Then the smoking hot female pool cleaner in cut-off shorts comes to clean the pool. Clyde, as it turns out, is quite the playboy, and when Linda's back is turned for about two minutes, she finds them together frolicking together (not actually having sex or anything, but acting in a way that could seem inappropriate for a married man to behave with a woman other than his wife). Anyway, Linda has a meltdown and says she wanted to have a honeymoon with Clyde and have another child with him. Clyde tries to calm her but says he is the way he is, he is the way he was written, and that in fact he can never change. Linda, devistated, goes into the city and to the top of a building and throws herself off to her death.
Clyde, who's supposed to be a hero, is sent to our world to help a grieving woman, yet his unfaithful ways are what end up driving her to suicide. Although I do believe he never intended to hurt her, rather than helping her he is what ultimately drives her to her doom. This part of the story I found particularly disturbing.
Thoughts?