(Note: this is a collection of the meanings attributed to the cards by some occultists in the past centuries. It does not reflect my own study or opinion of the cards. It is only meant as a quick comparative reference as I develop my own take.)

Paul Foster Case (and Ann Davies)

The specific divinatory meanings are thus based on the attributions of Chesed, the planetary forces of Jupiter and Neptune, the zodiacal influences of Cancer ruled by the Moon, and the astrological fourth house. Jupiter’s sphere of influence is Chesed. It co-rules the third decanate of Cancer besides being exalted in this zodiacal sign. Therefore the Four of Cups has a very strong Jupiterian influence of wealth and expansiveness. The Four of Cups corresponding to the third decanate of Cancer is the time period July 13 to July 22, ruled by Jupiter and Neptune.
In specific Tarot Divination its key meanings are:
Well Dignified: success in material things, but desire for something higher; a period of comparative comfort, yet a little confining, thus suggesting a measure of satiety; it is a symbol of contemplation and of the turning away from pleasure in quest of higher things; it intimates strong psychic influences in the life or environment of the Querent.
lll-Dignified: material gain, but through injustice; sorrows resulting from satisfaction of desire; getting what one has wanted but finding no joy in it.
Keyword: Surfeit
(From the Oracle of Tarot Course)

A. E. Waite

A young man is seated under a tree and contemplates three cups set on the grass before him; an arm issuing from a cloud offers him another cup. His expression notwithstanding is one of discontent with his environment. Divinatory Meanings: Weariness, disgust, aversion, imaginary vexations, as if the wine of this world had caused satiety only; another wine, as if a fairy gift, is now offered the wastrel, but he sees no consolation therein. This is also a card of blended pleasure. Reversed: Novelty, presage, new instruction, new relations.
(From The Pictorial Key to the Tarot)

Aleister Crowley

The Four of Cups is called Luxury.

The masculine nature of fire permits the Four of Wands to appear as a very positive and clear-cut conception. The weakness in the element of water threatens its purity; it is not quite strong enough to control itself properly; so the Lord of Pleasure is a little unstable. Purity has somehow been lost in the process of satisfaction.

[…]

This card refers to Chesed in the sphere of Water. Here, below the Abyss, the energy of this element, although ordered, balanced and (for the moment) stabilized, has lost the original purity of the conception.

The card refers to the Moon in Cancer, which is her own house; but Cancer itself is so placed that this implies a certain weakness, an abandonment to desire. This tends to introduce the seeds of decay into the fruit of pleasure.

The sea is still shown, but its surface is ruffled, and the four Cups which stand upon it are no longer so stable. The Lotus from which the water Springs has a multiple stem, as if to show that the influence of the Dyad has gathered strength. For although the number Four is the manifestation and consolidation of the dyad, it is also secretly preparing catastrophe by emphasizing individuality.

There is a certain parallelism between this card and the Geomantic figures Via and Populus, which are attributed to the Moon in her decrease and increase respectively. The link is primarily the “Change=Stability” equation, already familiar to readers of this essay. Four is an “awkward” number; alone among the natural numbers, it is impossible to construct a “Magic Square” of four cells. Even in the Naples Arrangement, Four is a dead stop, a blind alley. An idea of a totally different Order is necessary to carry on the series. Note also the refolding-in-upon-itself suggested by the “Magic Number” of Four 1 + 2 + 3 + 4 which is Ten. Four is the number of the Curse of Limitation, of Restriction. It is the blind and barren Cross of equal arms, Tetragrammaton in his fatal aspect of finality, as the Qabalists knew him before the discovery of the Revolving Formula whereby the Daughter, seated upon the Throne of the Mother, “awakens the Eld of the All-Father”.

For the meanings of Via and Populus, refer to the “Handbook of Geomancy” (Equinox Vol. I, No.2).

(From The Book of Thoth)

Golden Dawn’s Book T

FOUR cups: the two upper overflowing into the two lower, which do not
overflow. An Angelic Hand grasps a branch of lotus, from which ascends a stem bearing one flower at the top of the card, from which the white water flows into the two upper cups. From the centre two leaves pass right and left, making, as it were, a cross between the four cups. Above and below are the symbols Moon and Cancer for the Decan.

Success or pleasure approaching their end. A stationary period in happiness, which may, or may not, continue. It does not mean love and marriage so much as the previous symbol. It is too passive a symbol to represent perfectly complete happiness. Swiftness, hunting and pursuing. Acquisition by contention: injustice sometimes; some drawbacks to pleasure implied.
Chesed of HB:H (Receiving pleasure or kindness from others, but some
discomfort therewith).
Therein rule the great Angels HB:HYYAL and HB:MVMYH.

Etteilla

Boredom
Upright. This card, as far as the medicine of the spirit is concerned, means, in its natural position: Boredom, Displeasure, Discontent, Disgust, Aversion, Enmity, Hatred, Horror, Restlessness, Pain of spirit, Slight sadness, Affliction, Painful, Annoying, Unpleasant. – Saddening, Distressing.
Reversed. New Directive, New Light. – Index, Indication, Conjecture. – Augury, Foreboding. – Presentment, Foreboding, Predilection, Novelty.

MQS