A cupbearer is a servant who fills wine cups and serves wine to a lord. A cupbearer may also do other duties, such as setting a table and serving food. In Westeros, noble children often serve as cupbearers, and it is considered to be a great honor to be chosen to serve, especially at court. Both boys and girls may serve as cupbearers. A page or squire may also act as a cupbearer to his master.
- Aegon III Targaryen, for Queen Rhaenyra Targaryen
- Arya Stark, for Lord Roose Bolton
- Daeron Targaryen, for Lord Ormund Hightower
- Elmar Frey, for Lord Roose Bolton
- Obella Sand, for the wife of Ser Manfrey Martell
- Rhaelle Targaryen, for Lord Lyonel Baratheon
- Rhaenyra Targaryen, for King Viserys I Targaryen
- Tyrion Lannister, for King Joffrey Baratheon
- Tywin Lannister, for King Aegon V Targaryen
- Watkyn, for captain-general Harry Strickland
- The cupbearers of Queen Daenerys Targaryen
During the Andal invasion in the Westerlands, the First Men Kings of the Rock ennobled the more powerful of the Andal war chiefs, but took their children as wards, to serve as squires and pages and cupbearers in Casterly Rock, and as hostages against potential treachery.
During the Dance of the Dragons civil war, King Aegon II Targaryen offered his rival Queen Rhaenyra terms of parlay, including that her son Prince Viserys would be given a place of honor in his court as his cupbearer, but she rejected the offer.
After Prince Duncan Targaryen broke his betrothal with the daughter of Lord Lyonel Baratheon in 239 ᴀᴄ, a short rebellion ensued due to the Storm Lord's anger at his wounded pride. It ended only when Lord Lyonel was defeated in single combat, and King Aegon V Targaryen promised that his youngest daughter, Rhaelle, would wed Lord Lyonel's heir Ormund. To seal the bargain, Princess Rhaelle was sent to Storm's End to serve as Lord Lyonel's cupbearer and companion to his lady wife.
A Clash of Kings
Arya Stark, incognito as "Nan", is given the honor of becoming Lord Roose Bolton's cupbearer for her role in freeing the northern prisoners at Harrenhal. As a cupbearer, Arya dresses as a squire in Bolton livery, and performs such duties as fetching water and food and clothing, removing leeches from Roose's body, and cleaning his chambers.
A Storm of Swords
To mock him, King Joffrey Baratheon has his uncle Tyrion Lannister serve as his cupbearer at his wedding to Margaery Tyrell. After Joffrey dies of poison, this is used as evidence against Tyrion in his trial for the king's murder.
A Feast for Crows
Samwell Tarly recalls that when was he no more than ten, he was to be a ward of Lord Paxter Redwyne at the Arbor, to serve as his page and cupbearer, but his cravenly behavior when faced with the bullying of Redwyne's sons and fool caused his father to bring him home in shame instead.
Arianne Martell learns that when she was a girl, she was to have been sent to Tyrosh to be the Archon's ward and cupbearer, to secretly meet with her betrothed Viserys Targaryen. However, her father Doran abandoned that plan due to suicidal threats from his wife Mellario, who was already deeply upset that their son Quentyn had been sent away to be fostered.
A Dance with Dragons
To stymie the nightly killings of the Sons of the Harpy in Meereen, Queen Daenerys Targaryen has every noble family of Meereen who is of dubious loyalty send her a child as a hostage. The children are made her cupbearers, and serve in her chambers, serving wine and food and clothing and standing at guard at her door. Daenerys hopes having noble children as hostages will halt the killings, but it does not. However, Daenerys refuses to allow any harm to come to the children. She grows fond of them all, and ignores Skahaz mo Kandaq's counsel to kill one for every death done by the Sons of the Harpy. Ser Barristan Selmy instructs the boys in the ways of Westerosi chivalry.
When Daenerys disappears on Drogon's back, her cupbearers continue to serve her husband, King Hizdahr zo Loraq. After Barristan seizes control of Meereen in the queen's name, he again rejects Skahaz's advice to kill the young hostages. The cupbearers obey Barristan's commands, as Hand of the Queen.
When Jon Connington and "Young Griff" meet Harry Strickland and the rest of the Golden Company at Volantis, Harry tells his squire Watkyn to serve them wine. Watkyn pats Harry's feet dry after he has finished soaking them to treat blisters.
The Winds of Winter
- A Dance with Dragons, Chapter 11, Daenerys II.
- The World of Ice & Fire, The Westerlands.
- The Rogue Prince.
- The Princess and the Queen.
- The World of Ice & Fire, The Targaryen Kings: Aegon V.
- The World of Ice & Fire, The Westerlands: House Lannister Under the Dragons.
- A Clash of Kings, Chapter 47, Arya IX.
- A Clash of Kings, Chapter 64, Arya X.
- A Storm of Swords, Chapter 37, Jaime V.
- A Storm of Swords, Chapter 60, Tyrion VIII.
- A Storm of Swords, Chapter 66, Tyrion IX.
- A Feast for Crows, Chapter 15, Samwell II.
- A Feast for Crows, Chapter 40, Princess In The Tower.
- A Dance with Dragons, Chapter 23, Daenerys IV.
- A Dance with Dragons, Chapter 55, The Queensguard.
- A Dance with Dragons, Chapter 67, The Kingbreaker.
- A Dance with Dragons, Chapter 70, The Queen's Hand.
- A Dance with Dragons, Chapter 24, The Lost Lord.
- The Winds of Winter, Arianne I