John Cusack
Cusack plays Schwartz as a man of daring passion risking everything to express himself and the human condition through his puppetry. This layer initially subdues his selfishness, that is until he locks his wife in a monkey cage in order to enter John Malkovich and steal her lover. Once he inhabits Malkovich and has Maxine as his lover, his ego has become so big that he grapples with keeping his fame, or saving her life. His lust for Maxine is a great weakness that he is willing to pay any price for.
Cusack makes us feel for Craig in his depression, which brings the character to full form when he betrays his wife thus becoming an antagonist in this story.
Cameron Diaz
Lottie is sensitive, kind and possibly overly-optimistic about her relationship with Craig. She’s paying their bills while he tries to earn street money from puppeteering. She wants to start a family with Craig, but he’s not ready. Once Lottie enters Malkovich’s body she becomes aware that she wants gender reassignment surgery. She too falls in love with Maxine after going on a date and making love to her as Malkovich. This begins a crucial conflict that sets Craig off down a destructive path.
Diaz plays Lottie with a lot of empathy, which makes her character heartbreaking and hilarious all at the same time.
Catherine Keener
Keener plays Maxine very open, and straight to the point. She captures the lust and love of Craig, Lottie and John Malkovich. She’s a puppeteer, but she doesn’t play with dolls, she uses real people and she pulls Craig and John’s strings as far as she can, and ends up falling in love with Lottie through John’s body. She enters Malkovich, but only his subconscious mind so, of the main cast she is the only one who doesn’t have the true experience of being in his skin. This may be because in her life, unlike Craig and Lottie, she has more control because of her freedom to do as she pleases to whom she pleases.
Keener takes us on a journey of a character we barely care about because of what she does to other people, to someone who experiences just how lonely it is when only care about ourself.
John Malkovich
John Malkovich plays a version of himself in this film. His body has become a vessel that others to slip into through a door on floor 7 ½ of Craig and Maxine’s office. Craig, because of his master puppeteering skills is able to overtake John’s body and create the life he always desired. Just when the real Malkovich gets his body back from Craig’s exit, a whole slew of inhabitants including Dr. Lester take him over once again.
Malkovich is a joy to watch in that he plays the mundane and the maniacal so well that we always believe him.
Orson Bean
Dr. Lester is an 105 year old man who drinks carrot juice to stay young and still has the sexual desires of a twenty year old. He reveals that he is actually Captain Mertin, and has found a way to stay alive forever by finding vessels to inhabit on their 44th birthday. John Malkovich is his next, but things become complicated when he hires Craig, and Craig find the portal to Malkovich’s body.
Bean gives this character the youthful spirit he needs, always interested in the female form and defending his honor.