When it comes to inheritances, the courtroom can be a stage for dramatic conflicts and unexpected twists. But not all conflict happens in a court of law. From family feuds to hidden inheritances, Hollywood has often captured the intensity and complexity of these legal battles on the silver screen. At FastWill, we thought it would be fun to enter the world of will disputes through the lens of cinema. Get your popcorn ready as we discuss the best movies that showcase inheritance and family drama, sometimes leading to hilarious results.
"Knives Out" (2019)
Rian Johnson's modern murder mystery, "Knives Out," is probably the most memorable movie about a Will dispute. When renowned crime novelist Harlan Thrombey dies under suspicious circumstances, his eccentric family members become entangled in a battle for their share of the inheritance. Full of twists, turns, and an ensemble cast led by Daniel Craig, this film keeps audiences guessing until the very end.
The Bachelor (1999)
"The Bachelor" is a 1999 romantic comedy directed by Gary Sinyor and starring Chris O'Donnell. (Yes, there were famous Chrises before Evans, Pine, and Hemsworth). O’Donnel plays Jimmy Shannon, a commitment-phobic young man who suddenly finds himself on the verge of inheriting a massive fortune. However, there's a catch: in order to receive his $100 million inheritance, Jimmy must get married within 24 hours. Jimmy then embarks on a frantic quest to find a suitable bride. With the help of his best friend and a quirky wedding planner, played by Artie Lange (shout out to the Stern fans!) and Ed Asner, respectively, Jimmy navigates a series of hilarious and increasingly absurd situations in his search for true love and financial security. This is a movie about what happens when a grandpa leaves a bequest with a very strict deadline.
"The Descendants" (2011)
George Clooney delivers a remarkable performance in Alexander Payne's "The Descendants," portraying a man caught in the midst of a personal crisis. As the sole trustee of a family trust that holds valuable land in Hawaii, Matt King must navigate complex family dynamics and make weighty decisions regarding the inheritance. King is a lawyer whose wife gets in an accident and is suddenly in a coma. King then becomes the sole trustee of the family's valuable ancestral land. He soon faces a decision regarding whether to sell the land to a developer. This puts him under immense pressure from his extended family, who have their own vested interests in the decision. The film masterfully explores the impact of wealth and inheritance on relationships and personal growth.
"The War of the Roses" (1989)
Michael Douglas and Kathleen Turner deliver unforgettable performances in this dark comedy directed by Danny DeVito about the disintegration of a once-happy marriage. This movie isn’t strictly about estate planning, but it does show the fallout of a vicious divorce, which does indeed have something to do with leaving a legacy behind for one’s family. Oliver and Barbara Rose battle each other fiercely for possession of their home and all of its possessions. Turner and Douglas are at their best together, as “Romancing the Stone” and its sequel, “The Jewel of the Nile.” Their explosive feud highlights the lengths individuals can go to when greed and vengeance consume their lives.
“Rainman” (1988)
Dustin Hoffman won an Oscar for this 1988 film where a selfish man (Tom Cruise) finds out that his father died and gave his whole fortune to an autistic savant brother who he didn’t know about. Cruise’s character is immature and greedy and initially tries to just manipulate his brother into giving him some of the fortune. As the two embark on a road trip, he learns to admire and respect his brother, changing his entire attitude in the process.
"August: Osage County" (2013)
Based on Tracy Letts' Pulitzer Prize-winning play, "August: Osage County" offers a powerful exploration of a dysfunctional family gathering after their patriarch goes missing. As the family confronts their resentments and secrets, tensions rise, and the fate of the family home hangs in the balance. The film's stellar ensemble cast, including Meryl Streep and Julia Roberts, brings the complex characters and their conflicts to life.
“Brewster’s Millions” (1985)
John Candy and Richard Pryor headline Brewster’s Millions, a movie where an inheritance is contingent on the ability to spend $30 million in 30 days. (Sign me up for that task!) This movie is based on the 1945 original movie. In the later version, Pryor is a minor-league baseball player who inherits $300 million from his uncle. However, to get his hands on it he must first spend 30 Million dollars in 30 days. But he’s hampered by rules that forbid him from giving too much cash to charity or buying any new assets. He also can’t tell anyone about the Will’s odd rules.
“Howard’s End” (1992)
Based on the novel by E.M. Forster, “Howard’s End” is a British movie set in early 20th century England. When Helen Schlegel falls in love with Paul Wilcox, he does not return her affection. Then Margaret, Helen’s sister, starts to become friendly with Paul’s mother. Paul’s mother then surprises him by offering the woman the family estate, which is known as Howard’s End. When Wilcox dies, her Will goes missing (how convenient!) and it seems like the entire inheritance may go up in smoke. But Wilcox’s widower, Henry decides he fancies Margaret. Upper-crust hijinks ensue. (And consider this yet another reminder from FastWill to make sure there are several copies of your Will and people know where to find them!)
“The Grand Budapest Hotel” (2014)
Wes Anderson’s 2014 film “The Grand Budapest Hotel” starts with a classic dramatic conflict: a lawyer reads a will to a group of greedy family members who are hoping to inherit a very highly sought-after painting. (Our lawyers have advised us that there’s no such thing as a “reading of the Will.” We say, who cares? It’s called dramatic license for a reason! But to learn more, you should read our article on this popular dramatic element) Before the movie ends, it takes several exciting twists and turns that are in keeping with Anderson’s peculiar gifts. It turns out there’s actually another Will that has disappeared, and this sets chaos in motion.
