To do something thoroughly, completely, and in every way imaginable. For example, “We can go about solving this problem six ways from Sunday, but we need to pick just one of those approaches and go with it.”
“Six ways” can represent the six days after, or the six days before Sunday. Arriving at Sunday is inevitable, no matter which direction we go. There seems to be no clear origin for the idiom, which can be phrased in several different ways. The number used has ranged all the way from ‘two’ to a ‘hundred.’
Sunday was presumably chosen because it would have been regarded as the most significant day of the week. It may owe its success to the alliteration of Sunday with six and an association with a complete week.
From Morning Visits, in The American Monthly Magazine (1824):
“Yes, the careless, good for nothing feller, he’s always looking about six ways for Sunday, when he’s walking—I wish he’d stay at home.”
From The American Flint, Volume 18 (1926)
The glass manufacturers have it all over this man Ford six ways from Sunday. I know a lot of glassworkers who only work two or three days a week.
From Mrs. Hugh Fraser, Italian Yesterdays, Volume 2 (1913)
“…and so furiously interested in their miniature politics that the Government and the Opposition are ready to knock each other forty ways from Sunday every time they meet!”
From The Dairy (1937):
“There are, no doubt, many dairymen who know the food retailing business backwards and forwards and six ways to Sunday….”
Eric Partridge, in A Dictionary of Slang and Unconventional English, Fifth Edition (1961) says that the phrase “look nine ways for Sunday” is nautical slang from circa 1850 for “to squint.”
In the middle eighteenth century, the phrase ‘both ways from Sunday’ referred to the eye condition called strabismus, where someone’s eyes do not focus in unison, giving the appearance of looking in two different directions. The phrase evolved once again in the late 1800s in America to mean ‘every way possible.’
“Six ways to Sunday” was the title of a late 1990s mob-related movie staring Deborah Harry.
Dictionary of the Vulgar Tongue, by Captain Francis Grose, 1785, contains the following definition:
“SQUINT-A-PIPES. A squinting man or woman; said to be born in the middle of the week, and looking both ways for Sunday; or born in a hackney coach, and looking out of both windows; fit for a cook, one eye in the pot, and the other up the chimney; looking nine ways at once.”
This is an early American version:
“The brow projected exuberantly, though not heavily, over a pair of rascally little cross-firing twinkling eyes, that, as the country people said, looked at least nine ways from Sunday.” (Cobus Yerks, a short story by James Kirke Paulding, in The Atlantic Souvenir for Christmas 1828.)
There is a story that the saying dates back to the late 1100s when disbelievers and heretics were targeted by the Pope in Rome. Allegedly, the Pope sent out orders to every church that the last person to show up for Sunday service was to have the devil beaten out of him … six ways to Sunday. The punishment was to be meted out every day for a week until the following Sunday when another parishioner was tagged as the last one to show up for Sunday service.
Sounds like cruel and unusual punishment to me. I’d be inclined not to show up at all. But, considering what the church was like in those evil days, that would probably have resulted in my death. Blackmail does have its uses.