Scylla and Charybdis are two sea monsters of Greek mythology who were situated on opposite sides of the Strait of Messina between Sicily and Italy. They were located in close enough proximity to each other that they posed an inescapable threat to passing sailors; avoiding Charybdis meant passing too closely to Scylla and vice versa.
Odysseus was forced to choose which monster to confront while passing through the strait; he opted to pass by Scylla and lose only a few sailors, rather than risk the loss of his entire ship into the whirlpool. Jason and the Argonauts were able to navigate through without incident due to Hera's assistance, while Aeneas was able to bypass the deadly strait altogether.
A toned-down version of the Charybdis scene from the miniseries was featured in an episode of the children's animated series Mythic Warriors: Guardians of the Legend, which was titled "Ulysses and Penelope" and first aired on October 9, 1999. When Charybdis belched up the water, the force merely shot Odysseus's ship skyward rather than destroying it, and it dropped into the open sea and sailed away fully intact with Odysseus left behind.
In season four of the fox programme Prison Break the gang have to hunt down a data card called Scylla, after retrieving the first one they realise there are another five and soon go about tracking them down. It is also the name of the season premiere episode which can also refer to the deciding between two unattractive choices, they either retrieve Scylla and risk getting killed in the process, or go back to prison.
The phrase between Scylla and Charybdis, although infrequently used today, has meant having to choose between two unattractive choices, and is the progenitor of the phrase "between a rock and a hard place."
James Gillray used this metaphor in a caricature published June 3, 1793 and entitled Britannia between Scylla and Charybdis. In it, "William Pitt helms the ship Constitution containing an alarmed Britannia between the rock of democracy (with the liberty cap on its summit) and the whirlpool of arbitrary power (in the shape of an inverted crown), to the distant haven of liberty."
The phrase found new life in 2008 among journalists reporting on Microsoft's ongoing attempts to acquire Yahoo!. In an April 2008 ResearchRecap article, Christa Quarles of Thomas Weisel Partners was quoted, "Choosing between Microsoft and Google must seem like sailing between Scylla and Charybdis for Yahoo."
On May 1, 2008, All Things Digital columnist Kara Swisher published an online article titled "MicroHoo: Caught Between Scylla and Charybdis," describing Microsoft CEO Steve Ballmer's hesitance in reaching a deal with Yahoo! due to monetary issues. The story was even illustrated with the Henry Fuseli painting Odysseus in front of Scylla and Charybdis.