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The darkest moment for the lead character, Neo, in the film The Matrix (1999) is his death at the hands of Agent Smith.
This moment is the deepest point of the "hero's journey" and the ultimate "darkest before the dawn," as it appears to confirm that Neo is not "The One" and that the rebellion is doomed.
The moment occurs at the very end of the film after Neo has successfully rescued Morpheus with Trinity. Realizing his potential, Neo fights Agent Smith on equal terms and manages to defeat him.
However, the darkness deepens immediately:
Neo overcomes this darkest moment through a sequence of events driven by belief, love, and a complete transcendence of his limitations, which awakens his true power.
The summary inaccurately describes the iconic moment of Neo diving *into* Smith as 'plunging his hand' in.
The darkest moment for Neo in The Matrix (1999) is his death in Room 303. After being ambushed and shot point-blank by Agent Smith, Neo dies (his heart stops in the real world). He overcomes this through Trinity's intervention in the real world; she confesses her love and kisses him, fulfilling the Oracle's prophecy that the man she loved would be 'The One.' This connection revives Neo, who awakens with the ability to see the Matrix as code, stop bullets, and defeat Smith by diving into his avatar and destroying him from the inside.