I was fortunate to see The Last of Sheila at the Egyptian Theater last month, with stars Dyan Cannon and Richard Benjamin in attendance. It’s a movie that I’d seen previously and never really cared for, but after hearing director Rian Johnson describe it as a reference for his fantastic film Knives Out and considering it’s one of my mom’s favorite movies I figured I owed it a second chance. And not only did I thoroughly enjoy it more the second time around, it also inspired one of my Recasts posts! So, who could play in a modern-day remake of The Last of Sheila? (Note: Because Sheila ends up dying in the opening frames, she’s the only character I’m not recasting.)
The Plot: After his wife is killed in a hit-and-run, a prominent Hollywood director invites a group of friends onto his boat to play a game.
Originally played by: Richard Benjamin
My suggestion: Pedro Pascal
Aside from the fact that Pedro Pascal now looks like Richard Benjamin in the 1970s (their facial hair game is on point!), Pascal certainly has that edge that you need for Tom. As a character, Tom is a guy the audience presume to be one way but ends up being far more calculating and weasely than he’s given credit for.
Other suggestion: I hate to reuse actors if they’ve already appeared in another installment of this series, but I did think Oscar Isaac would also work. Isaac could easily play that battered, broken also-ran that is shown in Tom being little more than a script doctor.
Originally played by: James Coburn
My Suggestion: Matthew McConaughey
In the discussion after the viewing I saw, Benjamin explained that Coburn was a lot like his character in this movie, a gregarious firebrand with a devil-may-care attitude. And as Clinton Green, the director of both films and the on-screen murder mystery that plays out, it’s hard not to put in an actor with a similar blending of on- and off-screen persona. I just saw The Gentlemen a few weeks ago and McConaughey still conveys that effortless cool that’s similar to Coburn. You can certainly envision the bongo-loving actor sitting around in Coburn’s caftan, either seducing women or plotting to out his friends as the fakes they all are.
Other suggestion: If the remake tamped down on the character’s jokes and upped his calculating qualities I’d say Edward Norton.
Originally played by: Dyan Cannon
My suggestion: Kirsten Dunst
The character of Christine was based on Hollywood’s biggest agent of the 1970s, Sue Mengers. (Seriously, her life was fantastic and you should read her biography, Can I Go Now, immediately.) Cannon portrays the character as bubbly and fun, a woman you’d want to hang out with, but one who also has no problem talking trash about you behind your back. If you’ve watched Dunst in films like Bachelorette or seen her phenomenal work on Being a God in Central Florida than you know of her ability to smile out of one side of her mouth while stabbing a character in the back. I also went with Dunst as opposed to my younger suggestion below because, like Mengers, Dunst has been hardened by her time in the industry.
Other suggestion: Cannon was a tiny little thing and that’s important when you think of the power her character wields. The only other actress I could think of who could pull that off is Florence Pugh.
Originally played by: Joan Hackett
My suggestion: Cristin Milloti
Like my Tom casting, it’s hard not to notice how similar in looks Milloti is to Joan Hackett. The character of Lee is that of a child of privilege who struggles with self-esteem issues and guilt. She never believes she’s good enough. Milloti has famously played female characters similarly judged; you might remember her as Leonardo DiCaprio’s first wife in The Wolf of Wall Street. But Milloti has a tendency to take meek characters and give them an inner strength that the character of Lee desperately needs. If you watched Milloti in the Black Mirror episode, “U.S.S. Callister” you can see where she could elevate the character.
Other suggestion: I keep seeing Michelle Dockery here as well and I think a lot of that has to do with her keen ability to play a stoic Englishwoman a la Downton Abbey.
Originally played by: James Mason
My suggestion: Hugh Grant
One of the more laughable elements in The Last of Sheila is that Phillip Dexter is easily the most despicable character in the movie; he’s revealed to be a child molester. And yet the movie conveniently glosses over that, satirically poking fun at Hollywood’s ability to ignore the troubling if it suits them. That being said, who has a more magnanimous and lovable persona akin to James Mason in the 1970s? Hugh Grant. Everyone loves him and, for the purposes of this piece, people love when he plays a cad. And not to bring up The Gentlemen again, but after seeing that I could easily buy Grant playing a scummy, unrepentant louse who ends up being the greatest detective.
Other suggestions: You could really insert any English actor into this role, from Jeremy Irons to Michael Caine.
Originally played by: Ian McShane
My suggestion: Chris Pratt
The character of Anthony is that of a hanger-on, a man who’s only important because of the woman he married. And what better person to put in the role than the man commonly considered the worst Chris?
Other suggestions: I didn’t want to go the good-looking route because Anthony is a character whom you’re always wondering what his wife sees in him. But that being said you could add other cad actors like Jon Hamm or Sam Rockwell.
Originally played by: Raquel Welch
My Suggestion: Gal Gadot
Alice is the character who espouses pure Hollywood glamour, and in 1973 there was no actress who described the term “celebrity” quite like Raquel Welch. So I wanted to stick with an actress who is known as a pretty face, but holds hidden depths. Gadot has shown an ability to do comedy in stuff like Date Night and I think she’d be perfect as the naive Alice.
Other suggestions: Going off the idea of beautiful face first and foremost I also saw Margot Robbie here.
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A freelance film critic whose work fuels the Rotten Tomatoes meter. I've been published on The Hollywood Reporter, Remezcla, and The Daily Beast. I've been featured in the L.A. Times. I currently run two podcasts, Citizen Dame and Ticklish Business.