Henry Percy was originally a follower of Edward III of England, for whom he held high offices in the administration of northern England. He went on to support King Richard II. He was given the title of Marshal of England and created an Earl at Richard's coronation (1377). But, after Richard II created his chief rival, Ralph Neville, 1st Earl of Westmorland in 1399, he switched to the side of Henry Bolingbroke (later, Henry IV)
On King Henry IV's coronation he was appointed Constable of England and granted the lordship of the Isle of Man. Percy and his son, Henry Percy, known as "Hotspur", were given the task of subduing the rebellion of Owain Glyndŵr, but their attempts to make peace with the Welsh rebels did not meet with the king's approval. In 1403 the Percies turned against Henry IV in favour of Edmund Mortimer, 5th Earl of March, and then conspired with Owain Glyndŵr against King Henry.
The Percy rebellion failed at the Battle of Shrewsbury, where Hotspur was killed. Since the earl did not directly participate in the rebellion, he was not convicted of treason. However, he lost his office as Constable. In 1405 Percy supported Richard le Scrope, Archbishop of York, in another rebellion, after which Percy fled to Scotland, and his estates were confiscated by the King.
In 1408 Percy invaded England in rebellion once more and was killed at the Battle of Bramham Moor.
His position as a character in the Shakespearean canon inspired the character of Lord Percy Percy, Duke of Northumberland in the historical sitcom The Black Adder, set during the very late Plantagenet era.