‘buttered bread’ in phrases denoting fortunate situations

The image of one’s bread getting, or being, buttered is used to denote getting, or having, advantages, benefits:
– the phrase to know on which side one’s bread is buttered means to have the sense to know where one’s interest lies;
– the phrase to want one’s bread buttered on both sides means to want more than is practicable or than is reasonable to expect.

The notion conveyed by to want one’s bread buttered on both sides is similar to that expressed by the phrase you can’t have your cake and eat it (too), the French equivalent of which is, interestingly, on ne peut pas avoir le beurre et l’argent du beurre, literally you can’t have the butter and the money’s worth of the butter.

The phrase to know on which side one’s bread is buttered is first recorded in A dialogue conteinyng the nomber in effect of all the prouerbes in the englishe tongue compacte in a matter concernyng two maner of mariages (London, 1546), by the English playwright and epigrammatist John Heywood (circa 1496-circa 1578):

I knowe on whiche syde my breade is buttred.

The earliest instance of one’s bread buttered on both sides that I have found is in the form of a punning variant, which indicates that the phrase was already well established; this instance is from The Morning Post and Gazetteer (London) of Thursday 13th August 1801—the fact that buttered on both sides is in italics also implies that it was already in usage:

buttered on both sides’ - Morning Post and Gazetteer (London) - 13 August 1801

The Loan Jobbers, recollecting Mr. Addington*’s bargain for the Lottery, look forward to a new Loan with the utmost avidity. There will be no want of money while the terms are so good for the Lenders, who expect to have their slices of the Loan buttered on both sides.

* Henry Addington (1757-1844), 1st Viscount Sidmouth, British Tory statesman, Prime Minister from 17th March 1801 to 10th May 1804

Another phrase, to have one’s bread buttered for life, means to be well provided for. The earliest instance that I have found is in quotation marks, which indicates that it was already in usage; it is from The Carlisle Journal (Carlisle, Cumberland) of Friday 28th December 1849, which first quoted The Bucks Herald (Aylesbury, Buckinghamshire) as reporting that, during a shooting excursion,

just as Lord Canning was about to shoot at a hare, a bird fell from the gun of another of the party, and the Prince of Wales running forward in playful eagerness to pick it up, placed himself exactly between Lord Canning’s gun and the hare he was about to shoot, when Colonel Grey, observing the danger, rushed forward so as to cover with his person the object of a nation’s hopes, and in so doing received in the skirt of his coat upwards of twenty shots from Lord Canning’s gun, which, but for Colonel Grey’s promptitude, would in all probability have taken effect on the head or face of the Prince of Wales.

This was followed by this comment in The Carlisle Journal:

The story is truly a good one; and the Colonel’s bread appears to be “buttered for life.” But, alas! the goodness of the story is slightly marred—and the Colonel’s chances of promotion at once cut short by the announcement made by the Morning Chronicle of Wednesday that the whole is a fabrication!