Tony Stark, Avengers: Endgame
Robert Downey Jr. had never been killed on screen before this moment in Avengers: Endgame. This movie was one of the highest-grossing films of all time, and part of that is due to Tony Stark dying. This massive twist turned the end of a legendary trilogy into a serious tearjerker.
Emma Greenway, Terms of Endearment
There are a ton of films that end with the main character dying of cancer, but none of them really hit home like Emma Greenway's death in Terms of Endearment. She had to say goodbye to her two beautiful sons before she left, and their reaction felt like tearing open an old wound. Watch this movie if you want to hurt, badly.