[3] He had a younger brother, and four sisters:[3] Drury was admitted to Lincoln's Inn on 12 February 1517,[5] and entered the service of King Henry VIII before his father's death.
In the following year he was appointed a Groom of the Privy Chamber when Anne of Cleves arrived in England as Henry VIII's fourth bride.
[7][8] During the succession crisis after the death of King Edward VI, although he had been expected to aid Northumberland in his attempt to place Lady Jane Grey on the throne, Drury instead threw his support behind Princess Mary, and was appointed to the Privy Council early in Mary's reign.
As noted in the Guide to Medieval and Renaissance Manuscripts in the Huntington Library, Drury's name appears on folio i verso of the Ellesmere manuscript of Chaucer's Canterbury Tales:On f. i verso, s. XVI2/4, “Robertus drury miles [space], William drury miles, Robertus drury miles, domina Jarmin, domina Jarningam, dommina Alington,” referring to Sir Robert Drury (mentioned above as executor; speaker of the House of Commons in 1495 and a member of Henry VIII's Council), to his sons William and Robert, and to his 3 daughters: Anna, married first to George Waldegrave, and after his death in 1528 to Sir Thomas Jermyn; Bridget, married to Sir John Jernyngham (Jernegan, of Somerleyton); Ursula (d. 1521), married to Sir Giles Alington.
[5] Drury was buried in All Saints Church, Hawstead, where he is commemorated by a memorial brass and an inscription: Whilst he lived here was loved of every wight.