Why is Sisyphus in so much trouble?

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Why: He is pushing a boulder up a hill for eternity. Eternity. Do you know how long that is? What did he even do to deserve such a punishment?

Answer: He trolled Hades! Oh, this is funny:

Sisyphus was founder and king of Corinth, or Ephyra as it was called in those days. He was notorious as the most cunning knave on earth. His greatest triumph came at the end of his life, when the god Hades came to claim him personally for the kingdom of the dead. Hades had brought along a pair of handcuffs, a comparative novelty, and Sisyphus expressed such an interest that Hades was persuaded to demonstrate their use - on himself.

And so it came about that the high lord of the Underworld was kept locked up in a closet at Sisyphus's house for many a day, a circumstance which put the great chain of being seriously out of whack. Nobody could die. A soldier might be chopped to bits in battle and still show up at camp for dinner. Finally Hades was released and Sisyphus was ordered summarily to report to the Underworld for his eternal assignment. But the wily one had another trick up his sleeve.

He simply told his wife not to bury him and then complained to Persephone, Queen of the Dead, that he had not been accorded the proper funeral honors. What's more, as an unburied corpse he had no business on the far side of the river Styx at all - his wife hadn't placed a coin under his tongue to secure passage with Charon the ferryman. Surely her highness could see that Sisyphus must be given leave to journey back topside and put things right.

Kindly Persephone assented, and Sisyphus made his way back to the sunshine, where he promptly forgot all about funerals and such drab affairs and lived on in dissipation for another good stretch of time. But even this paramount trickster could only postpone the inevitable. Eventually he was hauled down to Hades, where his indiscretions caught up with him. For a crime against the gods - the specifics of which are variously reported - he was condemned to an eternity at hard labor. And frustrating labor at that. For his assignment was to roll a great boulder to the top of a hill. Only every time Sisyphus, by the greatest of exertion and toil, attained the summit, the darn thing rolled back down again.

Sisyphus is the first sinner Odysseus comes across in the Underworld.

“And I saw Sisyphus at his endless task raising his prodigious stone with both his hands. With hands and feet he' tried to roll it up to the top of the hill, but always, just before he could roll it over on to the other side, its weight would be too much for him, and the pitiless stone would come thundering down again on to the plain”

Source: MythWeb, Greek Damnation

The More You Know: The second sinner Odysseus encounters is Tantalus, who is sitting in a pool of water surrounded by grapes. Whenever he reaches for the grapes to eat, they rise up out of his reach; whenever he reaches down for water to drink, the water sinks away.

This is because he was a shitty host and a shitty houseguest:

• When invited to dine at Zeus's table in Olympus, he stole ambrosia and nectar.
• When he invited the gods to a banquet, he chopped up his own son Pelops, boiled him, and served him for dinner*.
  

*Only one god ate him, and only a little part of his shoulder; when the rest realized what was up, they reassembled him and gave him a shoulder made of ivory.

Tantalus's punishment is an example of contrapasso, which is the idea of a punishment that fits a crime (popular in Inferno). Fun examples:

• Bertran de Born - In life, instigated between King Henry II of England and his son. In Hell, his body is physically divided, carrying his decapitated head under his arm.
• Gluttons - In life, ignored others to feed their own self-indulgences. In Hell, forced to lie in a smelly, icy slush without sight, so they are alone forever.
• Allessio Interminelli - In life, a "brown-nosing" flatterer. In Hell, submerged in human excrement up to his nose.
  
• Francesca and Paolo - In life, had a lusty adulterous affair. In Hell, eternally stuck together in the most intimate of positions, with neither rest nor satisfaction, like wolves.