St. John "the Beloved" disciple holding a chalice with a dragon (stained glass, France)

"Like the flesh so warm that the thorn sticks into
Like the dream you know one day will come to life
Try to hold on just a little longer, stronger
It's the jewel of victory
The chasm of misery
And once you have bitten the core
You will always know the flavor
The split second of divinity
You drink up the sky
All of heaven is in your arms
You know the reason why
It's right there, all by itself"

(Faith No More, The Real Thing)

In the photo: stained glass of St. John, "the disciple whom Jesus loved", depicted in quite feminine features (characteristic of Renaissance art), holding a chalice with a dragon inside. Photographed at Saint Jacques Church in Cognac.

During the Last Supper Jesus picked up a cup of wine, popularly associated with the Holy Grail, and said to his disciples: “Drink this, all of you; for this is My blood of the covenant, which is poured out for many for the forgiveness of sins” (Matthew 26:27-29), but prior to the Last Supper he said to St. John “the Beloved” disciple and to James that they would drink the same cup as he himself is going to drink (Matthew 20:22).

According to the non-canonical second-century work the Acts of John, John survived drinking a poisoned cup served to him by Aristodemus, the chief priest of the temple of Artemis at Ephesus. In other traditions he was arrested and beaten by the Roman emperor Domitian, but remained steadfast. He was then poisoned, but he blessed the chalice and the poison turned into a snake and came out of the cup.

These stories found their way into the most popular medieval collection of saints’ legends, the 13th-century Legenda Aurea and therefore inspired this form of iconography associated with John. As emblem of the tales, John's chalice symbolizes the Christian faith prevailing over death.
St. John went on to live a very long life preaching and writing, and survived numerous near-martyrdoms.

Johannine literature refers to the collection of New Testament works that are traditionally attributed to St. John the Apostle or to a Johannine Christian community and are dated to c. 60–110 CE. The Cathars of Southern France had a special reverence for the Gospel of John.

The dragon, or Serpent, is a complex symbol in theology and in this context it could correspond to ancient symbolism of equilibrium of elements, also rooted in the Hebrew scripture where the Serpent itself was used at times as a healing totem in order to dismantle the potency of a venomous snake bite, not unlike how in the modern age we produce antivenom by milking the relevant snake species of its venom.

Outside the scope of orthodox or Catholic Christian theology, in specific Jewish or Gnostic Christian interpretations, the Serpent is also considered a source of wisdom rather than the cause of Original Sin, in this sense the Serpent is not the cause of mortality and death brought about by eating from the Forbidden Fruit but instead the Serpent is the one who offered the gift of wisdom and knowledge, despite the growing pains to follow.

A brazen Serpent that Moses was instructed by God to make in order to heal the Israelites from snake bites was an important relic at the Temple of Jerusalem until King Hezekiah destroyed it during his iconoclastic reforms because it became too venerated: “He removed the high places, and broke the images, and cut down the Asherah poles, and broke in pieces the brazen serpent that Moses had made; for until those days the children of Israel burned incense to it” (2 Kings 18:4).
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