- Lucky and Rebecca's parting at the end of "De Vil-Age Elder".
- Watching Rolly get bullied by his friends in the beginning of "Roll Out The Pork Barrel" and Spot get bullied by Lt. Pug in "Full Metal Pullet" easily qualify for this, especially if you've been bullied in real life. The latter gets a pretty big What the Hell, Hero? speech from Cadpig to Lucky.
- In the Yet Another Christmas Carol episode, we learn that Cruella's parents left her in the care of nannies to go on vacations, and they were absent at Christmastime. Young Cruella hoped they would send her a puppy for Christmas, and when they didn't, she'd take her frustration out on others.
- To put into perspective how little they cared about her, Cruella's parents would often send notes with their gifts that only barely acknowledged Cruella as their daughter.
- Lucky actually breaking down in sobs in "Lucky To Be Alone" after his rich relatives refuse to watch Thunderbolt with him.
- Mooch's treatment in "My Fair Moochie" shoves him straight into Jerkass Woobie territory. He tries so hard to make a genuine change from Jerkass to Nice Guy that his heartbroken reaction to Cadpig dumping him makes you feel bad for the poor guy.
Tear Jerker / 101 Dalmatians: The Series