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The Last Judgment, 1536-1541 by Michelangelo, Sistine Chapel, Vatican.
Michelangelo and the Vatican butted heads over the nudity in this colossal fresco of the second coming of Christ and the apocalypse. All of the souls are being judged and either ascending to heaven or falling down into hell. Some of the figures are coming to grips with their fates based on how they lived they lives.
Laocoon and his Sons (or Laocoon Group), Greek Hellenistic (most likely 42 -20 BC), Vatican Museums, Rome.
Laocoon warning about the Trojan Horse earned him the wrath Poseidon who sent serpents to attack him and his sons. Michelangelo was influenced by this work and the contortions of the body of Laocoon can be seen in many of his works, especially something like the Dying Slave.
Dying Slave
, 1513-16 by Michelangelo, Louvre, Paris.