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- Mrs. Savage is a witty, kindhearted, blue haired woman with a shifted viewpoint of humanity. The play is centered around her decision to hide the money which she has inherited from her late husband from her greedy stepchildren, to give away to those less fortunate or to fulfill others' random, yet important lifelong dreams. She dislikes her stepchildren, but learns to love the residents of The Cloisters, accepting their own realities and delusions with an open-mindedness that others on the outside do not.
- The elegant "mother" of The Cloisters, she believes she has a five-year-old son named John Thomas; in fact, John Thomas is a doll. During Mrs. Savage's stay at The Cloisters, Florence believes that John Thomas has the measles.
- Fairy is a compulsive liar who is obsessed with having others love her. She is unkempt throughout the play, but believes herself to be stunningly beautiful. She is also very childlike, behaving and speaking in the tone of a six-year-old.
- Once a military pilot, Jeff was shot down in the war, surviving a crash that killed all his men. He now believes that he has a scar on his face, which he constantly hides from others. He plays the piano, but is too shy to do so around other people. He is also married to Miss Willie, but does not remember that he is, due to the crash.
- Hannibal, once a statistician, was fired and replaced by an electronic calculator. He has then taken up the violin, which he wrongly believes he can play beautifully. He is a kind man with a vast array of knowledge stored in his sometimes sarcastic head.
- Mrs. Paddy paints with the quality of Hannibal's violin playing. She paints only seascapes, although she's never seen the ocean." The other patients say that Mrs. Paddy stopped talking when her husband told her to "shut up" one day, and she hasn't spoken since. She only speaks to announce what she hates. She hates "everything in the world."
- He is the eldest step-son of Mrs. Savage. He has been sent so many threatening letters that he is listed by Western Union as a "tangible asset"; Titus is the least popular senator in congress. He is sober, humorless, and direct. Titus also has a temper that tends to come out most when dealing with his mother.
- Lily Belle, the middle step-child, was once married to a Slovak prince, and has remarried five times since then. A celebrity heiress, she is arrogant, chic, and self-assured. She is also very selfish and is constantly putting forth the effort to make sure others are respecting her.
- The youngest step child of Ethel, Samuel has the distinction of being the judge with the most overturned decisions in the U.S. He walks in the shadows of his siblings, offering a sassy, short comment every once in a while, only to be shot down.
- The staff doctor for this wing of The Cloisters, Dr. Emmett is kind, warmhearted, and he works hard to help his patients.
- Miss Willie is an administrative assistant and nurse. She is married to Jeff, but struggles to pretend not to be because he doesn't remember her. He is the reason she is working here, but she is nonetheless extremely kind and understanding towards all the residents of The Cloisters.