!!First Film
* When this troper saw the dogs howling during the dog pound sequence, this troper saw many saddened dogs. I know the main four were just trying to distract the dog pound carriers, but the looks on those sad faces, especially the puppies in their pound cages. It...it was just so sad.
* Trusty's [[spoiler: DisneyDeath]]. Jock whimpering, then when he nudges Trusty and there's no response. That sad, mournful, cry he makes is ''awful''!
* Lady's TheReasonYouSuckSpeech to Tramp is ''very'' heartbreaking. Yeah, it doubles as a CrowningMomentOfAwesome, but you can hear the sadness in her voice when she does chew him out.
** Makes it doubly more saddening when Tramp leaves (because an angry Lady tells him to) and you can see from his expression that he really fell in love with her.

!!Second Film
* Scamp and Tramp's argument. A rather realistic insight on how a parent and a child with different views can turn into a heated debate.
* Angel revealing to Scamp [[spoiler: that she has been in five families.]] What makes this depressing is because of how numb her voice is.
* Lady's terrified expression on seeing and thinking that [[AdultFear her son had drowned]]. Thankfully, it turned out to be just a wig. But her expression and line ''"Oh, please"'' was just excruciating.