* The episode "Cats and Girls and Spaceships" where [[spoiler: Jim unknowingly kills the girl he had liked, and when she understandably fails to show up for their date afterward, he assumes she stood him up and never finds out the truth]]. Making it even worse. [[spoiler:The girl has no idea she was fighting the boy she loved, and her last thought is she'll never be able to see Jim again.]]
* [[spoiler:Hilda's death]] The tears that were shed were ManlyTears, for [[CrowningMomentOfAwesome Hilda has shown us all]] that ''[[{{Badass}} Outlaws]] [[TakingYouWithMe never go down easy]]''.
* [[spoiler: Harry's death.]]
* When Gene tries to rescue Melfina, [[BreakingSpeech Hazanko tries to turn them against each other by twisting Gene's words and painting him as the greedy badguy]]. It's hard to tell who's reaction is worse, Gene's or Melfina's.