It's a series! Some time ago this web site linked to a list of "25 Grammar Rules You Weren't Taught in School." Since the list appeared as a meme that may have been difficult for some readers to see, and since some readers like examples, here's a fuller and snarkier explanation of one of the rules...
1. Fewer bottles, less water.
"Less" was originally the comparative form of "little." It was one of those irregular sets of words like "good, better, best" and "many, more, most": "little, less, least."
"Fewer" was the comparative form of "few." "The rules of badminton are few. The rules of billiards are fewer."
The rule is: Use "fewer" when things can be counted, "less" when they can't be counted or are counted as single things.
If you had $56.78 in your pocket yesterday, and you were very frugal with heating in December, so your bill came to $42.46, and your municipality successfully upheld your right to pay the exact amount in cash, so after paying your bill you now have $14.32, you now have fewer pennies, or less cash, in your pocket. If you had to pay some sort of third-party handling fee, you have even less cash. We should always pay in cash because third-party handling fees add up to a substantial overpayment for the same things, or, the more often we pay in cash, the less we pay for whatever we buy.
Anyway, when the precise value of the coins and bills in our pockets are added up, we have more or fewer dollars and cents; while we are only thinking about the amount of unsorted stuff in our pockets, we have more or less cash. Pockets may also contain more or fewer cards, more or fewer keys, more or fewer tissues, but only more or less lint.
If, however, you decide to slim down your wallet by using up giftcards and not carrying store discount cards, as you use up the value of a card and pay the balance in cash you might cheerfully say "One less card!" You are now thinking of cards as an uncounted mass of clutter. If, as a cyclist or pedestrian, you bought things with the "One less car" slogan, and if they are what the name of the opposite-of-sainted Renee Good now brings to your mind, you think of motor vehicles as an uncounted mass of traffic hazards. These phrases are correct because these ways of thinking are correct.
A forgettable song of years gone by told the story of a man who had been, or claimed to have been, a lawyer in Philadelphia, trying to seduce someone else's wife. Maybe she was only his girlfriend--I forget. Anyway the woman's faithful husband, or boyfriend or whatever he was, heard the so-called lawyer proposing plans for her to leave him and run off with the lawyer, and committed a crime of passion. "There's one less Philadelphia lawyer in old Philadelphia tonight!" The singer was clearly thinking of Philadelphia lawyers as an uncounted mass of men with low moral standards, or a title claimed by such men. Whatever one might call them, the audience tended to agree, the fewer of them are left alive, the better.
Depending on the size of the animals you feed, you measure out more or less kibble, more or less grain, etc. If you don't have anything better to do than count the individual grains or kibbles in each measure, you might be able to report exactly how many fewer kibbles you gave the Chihuahua than you gave the Doberman.
Meanwhile, as the English language has developed, "little" has become one of a minority of words that have sets of regular and irregular forms. When thinking of a quantity of something that might or might not have a physical shape, we still say "little, less, least." When thinking of the size of something that has a single physical shape, many of us choose a word that came into English by way of Scotland and say "small, smaller, smallest," but some now say "little, littler, littlest" in contexts like "She had the littlest waist he'd ever seen." "Littler" and "littlest" are understood and are used in conversation by people who speak English well, but it's probably best to use "smaller" and "smallest" in written English.
"Little" also has an extra comparative form "lesser," which was probably never part of standard English conversation but which has become part of some phrases and names. Probably "lesser" entered standard English through jokes, like "worser," where nonstandard word use was part of the humorous effect. We say "the lesser of two evils," rather than "the less of two evils," most often to refer to voting for a candidate whose bad ideas we think may be easier to correct or recover from, in the absence of any candidate who we believe has good plans. "Lesser" also appears in proper names, but "less" is generally the word to use.
"Lessor" comes to English from a different source. It means one who leases, lets, or rents out property to another person, a "lessee." Someone who has two rental properties, both in terrible condition, might be described as a "lessor of two evils," though if the properties are all that bad the person probably won't be a lessor for very long.
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