What’s the DARKEST moment in the Mario franchise?

The Mario franchise has referenced the destruction of the Twin Towers prior to the 9/11 disaster in 2001 that entailed in the tragic deaths of 2,977 people with thousands of more suffering injuries and other trauma, and it left behind a legacy of lasting damage to people and weaponization of harmful politics. Some audio clips of passengers' last words on the hijacked airlines can be listened to ("I'm on an airplane that's been hijacked. If things don't go well, and it's not looking good, I just want you to know I absolutely love you..."; "We're all going to die in here").

The first time was the 1993 film where President Koopa vaporizes the building, but viewers can see holes and damage left behind on the buildings. The second time, Mario knocks into a building into the Club Nintendo comic, "Mario in Mariozilla".

Intriguingly enough, the World Trade Center is absent in both the New York Minute tracks in Mario Kart Tour and the skyline for the animated 2023 Illumination film, The Super Mario Bros. Movie. Both the game and the commercial instead show the progress of the rebuilt World Trade Center complex.
 
Back