He Really Can Act: Milton Berle gives a worthy dramatic performance in "That He Should Weep for Her".
Jerkass Woobie: Sherman Tyler from "A Cruel and Unusual Night". He killed a clerk while robbing a liquor store, was almost executed, then escaped to take revenge against the judge who sentenced him by putting him through a similar ordeal. He's also relentlessly self-centered, and he orders his Extreme Doormat wife around despite her obvious discomfort with his actions. On the other hand, the shooting was accidental, he actually feels sorry for the man he killed, and even the judge admits that Sherman's death row ordeal (he was put in the Gas Chamber, released at the last possible second, then faced the prospect of having to be executed again until his death sentence was finally commuted) was pretty horrible. And it turns out that he can't bring himself to kill the judge anyway.
Sherman's victim, Judge Howard Stimming, might also qualify. The end of the episode, where he sentences a man to death despite hearing Sherman's story and barely surviving his own kidnapping, is pretty unsettling.