In general, the appreciation of a high-quality anagram stems from the fact that it is such an outlandish coincidence that two related phrases should contain precisely the same letters. Many of the following attributes, constituting the hallmarks of a good anagram, are based upon this one principle.

The following has been paraphrased from erudite postings on the subject by Richard Brodie, William Tunstall-Pedoe, Richard Grantham and Jean Fontaine. Anagrammy-winning illustrations of each hallmark are on the right.

Aptness.

Relevance or reference to the subject is arguably the primary goal of anagramming. This generally involves the use of synonyms of key words from the subject in a paraphrase of, or commentary or joke about, the original. Occasionally, the anagram may even be the direct opposite in meaning (an antigram); however, anagrams that are neither synonymous with nor antonymous to their subjects are unlikely to be as widely appreciated.

Fire of London =
Dinner of fool.
     [nothing to do with it]
No finer flood.
     [a disaster all right, but the wrong one]
Inferno of old.
     [gets the disaster spot on]
(Jaybur, 2000)

Directness.

The more directly apt an anagram is, the better it is likely to be received. An anagram that is indisputably true but that only indirectly suggests the nature of its subject is occasionally referred to as an ambigram, though where that line lies is highly subjective. On the other hand, indirect but unexpected/whimsical angles on subjects are often well received, and anagrams of this sort that excel in all other areas have frequently gone on to pick up Awards.

Madonna Louise Ciccone =
I once made a conclusion.
     [undoubtedly she did, but the
      'gram is far too big a stretch]
A cool, demonic nuisance.
     [certainly apt!]
One cool dance musician.
     [but this one is both apt AND
      highly specific]
(David Bourke, 2000)

Grammatical correctness.

The better and more natural an anagram's grammar and expression, the more strongly it will convey its message. Even in the case of very short anagrams (where complete sentences are harder to form), something that sounds like a meaningful sentence element is to be preferred - simply reordering the words can make a big difference. Condensations that sound like newspaper headlines are also acceptable. Longer anagrams should have impeccable grammar, however, because the scope of having so many letters allows great flexibility in construction.

A carton of cigarettes =
Oft got a irate cancers.
     [atrocious grammar]
O, air to get cancer fast.
     [not perfect but acceptably
      headline-like]
I got a taste for cancer.
     [but this one is grammatically
      flawless]
(Meyran Kraus, 2002)

Avoidance of incorrect spelling.

This detracts from the quality of the anagram and makes it seem contrived or the author seem semi-literate. Regional variations in English (such as color/colour and realize/realise) are perfectly acceptable and can often be exploited to improve an anagram; uncommon alternative spellings for words are also acceptable, but not preferred. Old-fashioned spellings (hath, doth, aye, nay, 'tis) and shortened words like 'n' (for "and"), e'er or ma'am may also be employed, but these (especially 'n') are usually best avoided.

Gastroenterologist =
I let go torrents o' gas.
     [the use of "o'" is a minor flaw]
(Larry Brash, 2000)

Clever use of punctuation.

Whilst punctuation is often best avoided, it can definitely improve an anagram if cleverly used. There has been some debate as to whether the addition of an ampersand (&) qualifies as valid punctuation, or if this constitutes cheating; this is largely in the eye of the beholder, but to be safe it is best to avoid adding ampersands where possible.

Medicinal marijuana =
A cure? I'm in a damn jail.
     [works well as two brief phrases]
(Larry Brash, 1999)

Minimal use of interjections.

Whilst the use of "oh", "O", "eh", "hey", "ah", "ahem", "oy", "shhh", "OK" and so on can be a handy way of getting rid of leftover letters, excessive use of this device will damage an anagram. Ideally there should be none at all, but the use of a single, minor interjection (usually "O" or "Oh") in an otherwise excellent anagram is unlikely to be considered a major flaw.

The Great Pyramid of Cheops =
My God! Perfect Pharaoh site!
     [in this case, the interjection
      actually enhances the anagram]
(Richard Brodie, 2000)

Brevity.

The shorter an anagram is, the more unlikely and thus impressive its existence. Even as few as thirteen letters can be arranged in over a billion different ways, and though most of those arrangements are meaningless the implications for larger texts (even 20 to 30 letters) start to become clear. By about 60-70 letters (and particularly in the hundreds or thousands of letters) there are so many possible permutations that the clever coincidence that gives a short anagram its value has long since disappeared, and has been replaced by an appreciation of the author's skill.

Alive =
La vie.
(Adrian Hickford, 2002)

Careful use of non-keywords.

If the leftover letters fail to do justice to the anagram, the best keyword in the world will not save it. Apart from their potential to cause grammatical difficulties, leftovers can ruin an anagram by providing too much information in the form of an indirect addition or unnecessary description. If no apt or useful additions can be found, it is generally best to keep words made from leftovers as unobtrusive as possible.

A skeleton in the cupboard =
The artisan locked up bone.
     [good keywords, but 'artisan' is
      way off]
And lock up the irate bones.
     [better result with same keywords,
      but 'irate' is still wayward]
Bones are locked up in that.
     [non-keywords are now spot on]
(Allan Morley, 2001)

Well-mixed letters.

Repeating a key word (or a significant fragment of one) from the original in the subsequent anagram detracts from the cleverness of the result. The repetition of "the" and other short non-keywords is acceptable, of course. Occasionally, repetition is used deliberately for effect and the result is sometimes referred to as a parallelogram.

These girls are barely legal. =
The "girls" are really beagles.
     [deliberate repetition for effect]
(Richard Grantham, 2000)

Avoidance of contrived subject texts.

The best anagrams are those where the subject is a pre-existing, well-defined text. If the anagrammatist has resorted to making significant modifications to the original in order to make the anagram work, forcing a coincidence rather than trying to discover those generated by the subject alone, then the result is considerably weakened in the eyes of many. Altering a subject by adding the definite or indefinite article, or a person's middle name or title, is a much less serious flaw.

A Nintendo Gameboy =
Made to be annoying.
     [adding an "a" made this one work]
(James H. Young, 2001)

Self-sufficiency.

An anagram should be self-explanatory; it should not need any extra explanation or comment. It is best to concentrate for the most part on subjects that are well-known enough for the anagram to be clearly and widely understood; occasionally, however, the subject matter of an otherwise outstanding anagram may be obscure/regional or the anagram may refer to a little-known aspect of the original, in which case it may validly be accompanied by some brief details. In the majority of cases, however, an anagram that requires an explanation is likely to be weak.

Giovanni Pergolesi =
I love opera singing!
     [here, the anagram itself acts
      as sufficient explanation]
(Meyran Kraus, 2001)

Humour.

Be it witty, rude, sarcastic or whimsical, humour will always improve an anagram - especially if the punchline contains a real surprise. Rude anagrams are a particular favourite, but please remember they aren't to everyone's taste.

He's a legend in his own mind =
Neil Diamond, when he sings.
(Tom Myers, 2002)

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