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Tear Jerker: The Phantom Menace
Qui-Gon's death after the battle with Darth Maul.
That he tells Obi-Wan, who he has a father/son relationship with, to train Ani when he obviously wants to say something different is another one. The way he gently brushes his tears away is heartbreaking.
Before Anakin left Tatooine, he asked his mother if they would meet again. Those who watched the following film know that they will, but under very painful circumstances.