- The song, "Where is the Hope that I once Knew?" from Lost in Paris.
- Also, the fate of the other girls working at the lace shop. Not long ago, they were orphaned without families or close relatives to turn to. The Big Bad of the movie promised they would be well-cared for. Instead, they're abused and essentially enslaved by their bitter guardian. It's like the flipside of Madeline and her life with Miss Clavel.
- One of the CINAR songs, "Have You Seen Our Dog?", especially Madeline's solo. For anyone who has a beloved pet, and especially anyone who's ever lost a pet, it hits hard. Even the cab driver is crying.
- Another CINAR-era song, "Home, Home, I Want to Go Home" from Madeline and the Gypsies, especially the soundtrack version on the "Madeline's Favorite Songs" CD. Even the animals listening nearby are crying.
- Yet another song, "You Can Never Run Out Of Love" from the Around the World with Madeline singalong.
- The song "Without You" in Madeline and the Science Project. It's absolutely heart-wretching to hear Madeline sing about how she misses Genevieve while flashbacks are shown.
- Madeline reminiscing on her parents with the other girls in Lost in Paris, only to reveal that they're long gone. Everybody else is so saddened by her story that they all cry in unison.
- It gets even worse if we take all the animated stories as part of the same canon, including the CINAR specials. In the first special, based on the first book, her hospital room is filled with gifts from her Papa, and both parents appear alive and well in Madeline's Christmas. Since the girls don't look any older in Lost In Paris, her parents' deaths must have been fairly recent.
- The very first book and special, where Madeline wakes up crying in pain because of her appendix. It's every bit as upsetting as it is frightening to see a small child brought to tears as she is being rushed to the hospital. All her friends cry too as the doctor takes her away.
- In the episode Madeline and the Dog Show, the song "The Perfect Dog" actually caused the judges to break down and revert their decision to not let Genevieve participate in said show because she was a mutt.
- The fact that Pepito's voice actor, James Street, died in a crash in 2007.
- Madeline at the Ballet:
- The ballet teacher rejecting Madeline and no one else from his production of The Happy Swan because she's too short and can't pull off the leap correctly. Thankfully, prima ballerina Tatiana gives her a hand.
- Madeline hiding and crying uncontrollably after her failed attempt to dance in toe shoes causes a chain of accidents that ruin the dress rehearsal. Thankfully, once again Tatiana comes to her aid.
- The girls crying in bed when they're too sick to go home for the holidays in Madeline's Christmas. Thankfully, they get cured with magic porridge and their families end up coming to spend Christmas at the school with them, but still, they're sad when they think the holiday is ruined.
- In "Madeline and the White Lie", when Madeline breaks into Inelegant Blubbering upon being asked for her name.Artist: "Who are you?"Madeline: "I am...a liar!" (bursts out crying)
- In Madeline and the Toy Factory, Madeline is accidentally packaged in a doll's box and sent to a toy store, where she's bought as a present for a crippled, sickly Lonely Rich Kid named Giselle. For fun she pretends to be a remarkable doll who can walk and dance, and Giselle adores her, but a few hours later Miss Clavel arrives and the truth is revealed. It's a sad sight as Giselle cries when her precious new "toy," which she had started to view as her only friend, is taken away. The next morning she's too depressed to eat breakfast, as is Madeline in her guilt for having tricked her.
- The girls crying in Madeline and the Singing Dog when they think Genevieve is happy as a singing star and better off without them, and Genevieve herself crying and whimpering because she misses the girls after her fans all leave. Really, any time the girls are separated from Genevieve is a Tear Jerker.
Tear Jerker / Madeline