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Henry Oldrey is a playable character in Castlevania: Legacy of Darkness. Apart from having his own adventure in the game, Cornell encounters him in his own journey, at which time Henry is only 10 years old. As an adult, Henry is a big and powerful man, sports armor in the style of a medieval knight, and uses a gun as his main weapon.

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Cornell's first encounter with Henry takes place in the Villa, which until then had been Henry's home. However, terrible things have happened lately: Henry's father has been turned into a vampire and he is trying to do the same with his wife and son, while at the same time evil beasts are surrounding the building. Henry, having dared to enter the nearby labyrinth, is attacked by a chainsaw-wielding madman, and only Cornell's appearance saves his life. Cornell had been asked by Henry's mother to save him, while she herself had decided to remain in the Villa, regardless of her fate. After having been guided through the lethal labyrinth by Cornell, Henry is able to escape into the forest.

Henry meets up with Cornell again at the game's first ending, and along with him and his sister Ada, goes into the new day with the intent of beginning a new life.

When we meet up with Henry again, eight years have passed and both he and the world have changed. The forces of darkness are again stirring and there have been disturbing reports of small children being kidnapped from nearby villages. Henry, now an accomplished warrior and a Holy Knight of the Church, receives the task of rescuing the six missing children from Dracula's Castle. However, he has little time to accomplish his task (one week), as it has been foreseen that the castle will crumble in seven days. Joined by his fellow colleague of the church, Reinhardt and the sorceress Carrie, they set off on a quest to stop Dracula.

Unlike the adventures of the other playable characters, Henry's quest hardly features cutscenes or other kinds of plot-driving measures, and is open-ended rather than linear (the order in which the children are saved is decided by the player). There is no main enemy or boss to defeat, and the ending sequence (mildly altered depending on how many children were rescued) is unusually brief.

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