The phrase bread always falls with the buttered side down, and its variants, express picturesquely the supposed law of nature—known as Murphy’s Law and, less politely, as Sod’s Law—according to which, for any given situation, the worst of possible outcomes will inevitably occur.

Before and after becoming the topic of a set phrase, the fact that bread falls with the buttered side down was occasionally mentioned as one of the misfortunes characteristic of days on which everything seems to go wrong—cf. bad hair day.

For example, it is one of the many incidents punctuating the visit that the anonymous narrator of Town Life—published in The Wilmingtonian (Wilmington, Delaware) of Thursday 25^th December 1823—pays to his “wife’s half-sister’s, Mrs. Tumble-up’s”, who lives in the town of S——:

Sister said, brother you had better try some of our Hyson; I gues [sic] you would be apt to like it. So I thought I must do as l was bid again, and I got my tea-cup in my hand, but the very saucer burnt my fingers. At this moment along came the big negro, with another tin platter full of bread and butter.—Now had you seen me you would have pitied me from your soul; for in one hand I held the tea-cup as hot as a warming pan, in the other a great hunk of bread and butter. I could not tell which way to go to work to eat the one and drink the other. The sweat rolled down my face with mere vexation; but at length, I being doleful hungry, l made a greedy bite at my bread, which tilted the tea-cup in my other hand, so that sister’s hyson slopped over on my fingers, and it scalded me so intolerably that down went bread and butter, tea-cup and all. The buttered side of the bread fell spat on the knee of my new leather breeches, and the hyson after scalding my knee to a blister, ran down my boot to my very toe.

It was likewise one of the many misfortunes mentioned in a story published in the Portland Advertiser and Gazette of Maine (Portland, Maine) of Friday 31^st July 1829—story reprinted from the Boston Mercury:

The Last Day of Grace.
————Ye powers!
That dreadful note!—Day of Doom.

I awoke in the morning before the usual time. My sleep had little of quiet. I dreamed of duns and Deputy Sheriffs. I was no better off when awake, for my note was to be paid by two o’clock, and my pockets were empty. I put on my clothes. Dressing is bad enough at any time; but dressing when you have a note to pay before night is horrible. Every thing goes wrong. You fasten the wrong buttons, stick pins in your flesh, and twist your clothes villaniously [sic] out of shape.
At breakfast nothing was better. The coffee was scalding hot; the toast fell into my lap, buttered side down, (Nankeens on.) No appetite. Felt dyspeptical.

There seems to be an allusion to the inevitability that bread will fall with the buttered side down in the following passage from the account of a fictional election meeting held by the little boys of Trenton, published in the Emporium and True American (Trenton, New Jersey) of Saturday 1^st October 1831:

It was observed while haranging [sic] the “wondering crew,” that Pat kept one hand behind him, in which it was supposed he held his bread and butter. This gave rise to a whisper that if he made such violent exertions, he might possibly drop his piece, the buttered side downward.

This inevitability is explicitly mentioned in A Dinner at Poplar Walk, an unsigned short story published in The Albion, or British, Colonial, and Foreign Weekly Gazette (New York City, N.Y.) of Saturday 5^th April 1834:

“Well, how are you, eh?”
“Uncommonly well, thank ye,” said Minns, casting a diabolical look at the dog, who, with his hind-legs on the floor, and his forepaws resting on the table was dragging a bit of bread-and-butter out of a plate, which, in the ordinary course of things, it was natural to suppose he would eat with the buttered side next the carpet.
“Ah, you rogue!” said Bagshaw to his dog.

The earliest occurrence of the phrase that I have found is from the Boston Daily Advertiser (Boston, Massachusetts) of Thursday 9^th April 1829:

From the New York Courier.

Poetical.—Our readers may remember the beautiful apostrophe in Lalla Rookh *, beginning
     “Oh ever thus from childhood’s hour
     I’ve seen my fondest hopes decay;
     I never loved a tree or flower
     But ’twas the first to fade away,” &c.
In a late Georgia Courier we find the following parody—the last stanza is exquisitely affecting and is founded on the eternal experience of childhood.

     ’Twas ever thus from childhood’s hour,
        I’ve seen my fondest hopes decay;
     I never had a bird or flower,
        That did not fly or fade away.

     I never had a little kit,
        To purr so softly on my lap,
     But fortune’s malice follow’d it,
        To kill by cur, or school-boy rap.

     I never had a bit of toast
        Particularly good and wide,
     But fell upon a sanded floor,
        And always on the butter’d side.

* Lalla Rookh (1817) is the title of an Oriental romance by the Irish poet Thomas Moore (1779-1852).

A variant of the phrase occurs in the Greensborough Patriot (Greensborough, North Carolina) of Wednesday 9^th January 1833:

The crisis. The president’s proclamation has thrown consternation into the ranks of those who advocate the peaceful remedy. A moon-calf in the Richmond Enquirer, recommends that the legislature appoint four men, good and true, as commissioners, to repair forthwith to Columbia, and implore the convention to reassemble, and rescind the ordinance, or beseach [sic] the legislature to postpone the period when it shall take effect. Tis [sic] his [sic] like giving a piece of bread and butter to a peevish child, and then using persuasions to prevent it from dashing the buttered side on the floor!

The phrase occurs in the Cleveland Daily Advertiser (Cleveland, Ohio) of Thursday 29^th January 1835:

We had thought some of apologizing for the delay attending the publication of our last number, but foreseeing that this week’s paper would also be ‘behind time,’ we concluded to wait and club both apologies together. None but a printer can fully comprehend the thousand and one mishaps which lie in wait for a moving printing office; […] the number of those who have business to be settled, and are as sure to call in the nick of time as the buttered side of bread is to fall downward […].