Tear Jerker / Outlaw Star

• Episode 4 "When the Hot Ice Melts", Hilda's death. The tears that were shed were Manly Tears, for Hilda has shown us all that Outlaws never go down easy.
• Episode 15, "The Seven Emerge", is a bleak portrayal of just how scared to die Gene is, and his first experience of being in way over his head. Threatened by the assassin Shimi, Gene haughtily proclaims that he can easily defeat him. Then he gets his ass handed to him. Repeatedly. During the battle with Shimi, Gene gets shot in the stomach, every member of the crew has a fake-out death, and they only win by sheer dumb luck. It's horrible just how close the Outlaw Star crew came to being utterly annihilated, and it was only that Shimi took pity on them that they escaped alive.
  • There's also the scene about halfway through the episode where Melfina comes to visit Gene, and, convinced that he's going to die but trying not to show it, he tries to make her sleep with him, which terrifies her. In this case, his lecherousness is not played for laughs. He angrily asks Melfina why she was created, and she starts crying, saying that she doesn't know. It's the first time Gene is faced with what a flawed person he is. Thankfully, he slowly gets better.

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• Episode 20 "Cats and Girls and Spaceships", where Jim meets Hanmyo and develops a crush on her. Which ends with a grappler ship duel with the Outlaw Star, who weren't aware the enemy ship was being piloted by a child. So when Jim heads back to the park afterwards, expecting to meet her for their date, she inevitably doesn't show. Made worse, since Hanmyo hadn't known she was fighting Jim, either.
• Episode 25 "Maze of Despair," despite how unhinged he's been throughout the series, Harry's death is surprisingly poignant.
  • Equally, Ron's reaction to Harry's near-death is poignant as well and highlights despite them both being unrepentant opportunists and otherwise complete scum, they clearly do care about one another.
  • When Gene tries to rescue Melfina, Hazanko tries to turn them against each other by twisting Gene's words and painting him as the greedy bad guy. Either out of a desire to be malicious and turn them against one another, or because he truly believes that's exactly what Gene wants, just like himself. It's hard to tell who's reaction is worse, Gene's or Melfina's.