Heywood is a member of Red's gang who are long sentence serving convicts.
He was portrayed by William Sadler.
He is first seen taking bets on who would will crack the first night. Heywood bets Fat Ass, wins this bet and gets a pack of cigarettes. Later, he hears of Fat Ass's death and is visibly shocked. After Andy gets the other prisoners beer, Heywood tentatively offers it to him and becomes his friend.
Heywood takes another big part in 1954 where one of their friends crack, Brooks Hatlen. As Floyd tells Andy and Red this, they come rushing over to see what the problem is. There, they see Brooks holding a knife to Heywood's throat. Brooks is about to be released from prison after 50 years, and he believes that killing Heywood would be the only way for him to stay. Andy and Red calm Brooks down and Brooks eventually accepts his fate.
A short while later, Brooks has sent the gang a letter saying he killed himself. Heywood thought that Brooks was crazy for holding a knife to his throat and went on about how insane he went, however Red tells him to knock it off. Red then says that after being in prison so long he was institutionalized.
Despite not liking Andy at first, he becomes good friends with him as time goes on and grows to admire him. Heywood can be seen to have great respect for Andy when Andy escapes from Shawshank prison in 1966. Over the next year, he, Red, and Floyd have conversations and laugh about Andy's story.
Before his sentence Heywood was arrested for stealing butt plugs.