After making his well-received indie debut with Bottle Rocket and proving he wasn’t a one-trick pony with the coming-of-age gem Rushmore, master of quirk Wes Anderson helmed The Royal Tenenbaums. The tragicomic saga of a deeply dysfunctional family of child prodigies suffering simultaneous midlife crises, The Royal Tenenbaums is often called Anderson’s magnum opus (although it faces strong competition from The Grand Budapest Hotel).
While Gene Hackman and Anjelica Huston led a perfect cast in Anderson’s 2001 masterpiece, The Royal Tenenbaums would’ve starred very different actors if it was made today.
Robert De Niro As Royal Tenenbaum
After proving his dramatic chops in iconic movies like The Conversation and Unforgiven, Gene Hackman showed off his comedic abilities with the role of Royal Tenenbaum. Robert De Niro is a similar screen legend with both dramatic and comedic talents who got his start a little later than Hackman.
He’s been doing more comedy lately with movies like Dirty Grandpa and The War with Grandpa, but he needs one that’s actually well-written like his earlier classics Midnight Run and Meet the Parents. Royal would’ve been a fantastic comedic role for a contemporary De Niro.
Tilda Swinton As Etheline Tenenbaum
Anjelica Huston’s fiercely funny turn as the Tenenbaum matriarch in The Royal Tenenbaums established a long-running working relationship with Anderson. She went on to play Steve Zissou’s estranged wife in The Life Aquatic and the Whitman brothers’ estranged mother in The Darjeeling Limited.
If The Royal Tenenbaums was made today, the role of Etheline might be played by a more recent Anderson regular, Tilda Swinton. Just like Huston, Swinton would nail Etheline’s combination of motherly love, deadpan humor, and humble intellectualism.
Kevin Hart As Eli Cash
Originally played by co-writer Owen Wilson, Eli Cash is a childhood friend of the Tenenbaums who grew up to become a popular author. His alternate-history western novel Old Custer has made him a “literary celebrity” and he’s having an affair with Margot.
Wilson played Eli as warm, likable, and relatably flawed. Today, the role could be filled by a similarly endearing, widely adored comedy star: Kevin Hart. Hart is one of the few bankable leading men left in a franchise-dominated Hollywood, and he needs to take on subversive roles like Eli Cash to prove his abilities as a dramatic actor.
Emma Stone As Margot Tenenbaum
Played to perfection by Gwyneth Paltrow, Margot is perhaps the Tenenbaum child who feels the least connected to Royal. Since he would always take the opportunity to point out that she was adopted, she grew up feeling indifferent toward her father.
Not only does Emma Stone look the part; she played the estranged daughter of a flawed father brilliantly opposite Michael Keaton in Best Picture winner Birdman. She also demonstrated in The Favourite that she can fit in with a filmmaker’s distinctively offbeat sense of humor.
Michael Stuhlbarg As Raleigh St. Clair
The role of Margot’s deeply unhappy husband Raleigh St. Clair was originally played by Bill Murray, who’s been in every Anderson movie since Rushmore. But Raleigh isn’t a Murray-type role in the slightest. Murray gave possibly his most understated performance to date as this character.
Today, the part could be played brilliantly by Michael Stuhlbarg. Thanks to A Serious Man, The Shape of Water, and Call Me By Your Name, Stuhlbarg is Hollywood’s go-to guy for timid, insecure intellectuals.
Ryan Gosling As Richie Tenenbaum
The main characteristic of Richie Tenenbaum, originally played by regular Anderson collaborator Luke Wilson, is his love for his adopted sister Margot. So, anybody who plays this role needs to share palpable romantic chemistry with the actor playing Margot.
Ryan Gosling co-starred with Emma Stone as love interests in La La Land, Crazy Stupid Love, and Gangster Squad. He also proved in movies like The Nice Guys that he has the dry comedic chops to pull off an Anderson role.
Denzel Washington As Henry Sherman
Henry Sherman is Etheline’s accountant and later fiancé, played by Lethal Weapon’s Danny Glover. Henry is one of the most sensible characters in the movie. He needs to be played by an actor who, like Glover, can handle the dramatic nuance of playing a widower trying to move on, but also nail the comic line deliveries in his interactions with Royal.
Denzel Washington is one of the most celebrated dramatic actors in the world, and has given audiences plenty of laughs with pitch-perfect line deliveries like Training Day’s “King Kong ain’t got sh*t on me!”
Jonah Hill As Chas Tenenbaum
Chas Tenenbaum, originally played by Ben Stiller, is a prodigious business mind who’s had an impressive financial portfolio since he was a little kid. But his character is defined by the crisis he faces following the death of his wife. He becomes overly safety-conscious after she dies in a plane crash, moving his sons Ari and Uzi into his mother’s house and forcing them to work out 16 times a week.
Stiller nailed the comedic absurdity of Chas’ overprotective parenting, but also brought heartfelt nuance to the complicated emotions behind it. Jonah Hill got his start in raunchy hard-R comedies like Superbad and 21 Jump Street, but he proved in Cyrus that he’s just as adept with quirky, tongue-in-cheek tragicomedy.