Henry Oldrey is a playable character in Castlevania: Legacy of Darkness for the Nintendo 64. 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, while using a gun as his main weapon.
Cornell's first encounter with Henry takes place in the Villa, which until then had been Henry's home. But terrible things have happened lately, Henry's father has been turned into a vampire and is trying to do the same with his wife and son, while evil beasts are surrounding the building. Henry, having dared 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 her son, 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 with Cornell and Ada, goes into the new day intent on beginning his 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 in villages being kidnapped. Henry, now an accomplished warrior and an 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 you can save the children is for example decided by the gamer). 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.
Henry's allocated arena for exploration is far smaller than that of the other three playable characters, only six levels (each containing a specific child to rescue) are available. While this would lead many gamers to dismiss this section as an inferior and forgettable part of the game, it should be noted that Henry's quest provides the main opportunity to unlock secret characters and costumes, making it well worth the while for gamers wanting to explore all Legacy of Darkness has to offer.
- Whenever Henry saves a child, the "victory" fanfare is a few bars from the song Theme of Simon Belmont, first introduced to the series in Super Castlevania IV.