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The Top 8 Estate Planning Movies To Watch In 2022

The new year is in full swing and there’s no better time to start planning ahead by creating an Estate Plan. Check out our movie recommendations to get you inspired!

It’s a new year, and hopefully one of your new year’s intentions is to set up your estate planning game. If COVID-19 taught us anything, it’s that life is unpredictable and that you can suddenly find yourself in dire need of an estate plan. Educating yourself is a great first step. You can read books, articles, or even attend virtual estate planning workshops that are extremely informative. However, don’t forget that you can also expose yourself to estate planning themes and ideas through entertainment.

After all, estate planning doesn’t always have to be serious. It can also be fun and explorative! With that being said, why not add some movies that incorporate estate planning themes to your watchlist in 2022? We reveal some of our favorites below.

8 Movies About Estate Planning To Watch This Year

Spoiler alert! If you look at the list of movies below, you may have already seen several of them. Did you realize that these movies had themes of estate planning in them? Perhaps your answer is “no.” Themes related to estate planning often pop up in our media and culture without our even realizing it. 

Without further adieu, here are our top picks for movies that touch on estate planning in some shape or form. You can find these movies on Apple TV or your preferred streaming service. We hope you brought your popcorn! 

1. The Descendants

George Clooney and estate planning? Talk about a super-charged combo! This Oscar-winning movie portrays Matt King, the sole trustee of a family Trust that holds 25,000 acres of untouched land on Kauai, the Hawaiian garden island . 

Due to the rule against perpetuities, the King Family Trust will expire in seven years. This means that the family must decide what to do with the land as soon as possible. While Matt is faring well due to his career as a Honolulu-based attorney, many of his large family’s members have squandered their inheritances. Therefore, he is receiving pressure from several brothers and cousins to sell the land to developers. While the sale could make the family hundreds of millions of dollars, the potential development of such rare pristine land is controversial and is garnering public opinion. This film follows Matt King as he is faced with his heavy responsibility as the family trustee that forces him to confront family matters. 

Watch this film to get a sense of how large the responsibility of serving as a family Trustee is, but also to enjoy beautiful scenes filmed in Oahu and Kauai. 

2. Knives Out

This hit film has a sequel coming out in 2022, so there’s no better time to catch the first one if you missed it, or rewatch it (we know we have). Knives Out is packed with a star-studded cast, including Daniel Craig, Ana de Armas, Chris Evans, Jamie Lee Curtis, and the late Christopher Plummer. 

The murder mystery centers around the passing of famed novelist Harlan Throneby and his incredibly wealthy family. Packed with endless twists, complicated family dynamics, and a dramatic reading of the Will, this film has it all. Watch Knives out if you want to see estate planning conflicts play out in a fresh, engaging way. 

3. Framing Britney Spears

If you haven’t at least heard of the Britney Spears conservatorship battle, you may as well be living under a rock. The 2021 New York Times documentary “Framing Britney Spears” follows American pop star Britney Spears in her origin story that eventually led to her 2007 breakdown and resulting conservatorship. 

The conservatorship involuntarily placed Britney under control of her father Jamie Spears from 2008 through 2021. Fans of Britney started the #FreeBritney movement when they began to feel as though the conservatorship was no longer necessary nor fair. In essence, the conservatorship was deemed inappropriate as Britney appears fully healthy and able to make her own decisions regarding her body, career, and finances. 

This documentary is the perfect way to get up to speed on Britney’s conservatorship controversy, as well as to get a glimpse of when an extreme case could go wrong.

4. Little Big League

This 1994 family comedy follows Billy, a 12-year-old who becomes the owner of the Minnesota Twins baseball team overnight. How did this happen? His late grandfather, who owned the Twins, bequeathed the team to Billy in his estate. 

Join in on the family fun while Billy undergoes the trials and tribulations of owning a major league baseball team. Although the film does not hold much legal footing, it makes for great entertainment. It also presents a good hypothetical on the appropriateness of bequeathing assets or property to underaged beneficiaries.

5. Rain Man

Who knew that an estate planning concept could inspire one of the world’s most beloved films in film history? This 80’s classic won 4 Oscars and envelops multiple estate planning themes, including conservatorship, guardianship, and inheritances.

Tom Cruise plays Charlie, a selfish young man who finds out that his late father’s estate goes to an anonymous trustee. The estate is worth $3 million, so you can imagine why Charlie would go to great lengths to find out the identity of the anonymous trustee. 

We don’t want to divulge much more information as it would ruin the plot, but trust us when we say that this movie is a must-see! 

6. The Bachelor

Have you ever thought about creating a bequest, but with a condition? The Bachelor is a 1999 comedy that illustrates what could happen when a Trustor leaves behind a wacky conditional bequest.

Jimmie Shannon, played by Chris O’Donnell, is a serial bachelor who just can’t make a commitment. He is surprised to find out that he is the heir to his late grandfather’s $100 million fortune. However, this bequest comes along with a big catch. Jimmie won’t inherit this great fortune unless he satisfies the condition: that he gets married by 6:05pm on the day he turns 30. Even worse? His birthday is tomorrow!

Want to find out if Jimmie is able to meet his grandfather’s condition within 24 hours? You’ll just have to watch to find out.

7. The Ultimate Gift

Conditional bequests appear to be one of the movie industry’s most favorite estate planning themes. The Ultimate Gift is a 2006 drama stars Jason, a spoiled young man who shows up late to his late grandfather’s funeral. Red, his grandfather, leaves him one last message: a video message relaying Jason’s inheritance. 

In this video, Jason’s grandfather explains that his inheritance is a gift that has to be earned (hence, the conditional bequest.) This heartwarming film follows Jason who undergoes a series of challenges.

Watch to find out whether or not he transforms into someone who is worthy for this Ultimate Gift. 

8. Brewster’s Millions

We’ll end this list with our third and final movie about a conditional bequest. Richard Pryor stars in this film as Monty Brewster, a minor league baseball player. 

Brewster finds out that he had a great-uncle, whom he never met, who left him his $300 million fortune in its entirety. However, he can’t inherit the fortune unless he completes a challenge with several conditions. 

Here’s the challenge: either receive $1 million upfront or inherit the entire estate of $30 million by spending $30 million in 30 days. Here are some of the conditions:

  • Brewster may not own any assets at the end of the 30 days (unless they were already his)

  • He can not tell anyone

  • He cannot give any of the money away or waste it (such as by buying valuable items and destroying them for the sake of spending money)

  • He may donate 5% to charity and lose 5% to gambling, but that is all

  • He must get value by hiring others for services

This hilarious film is a must-watch to find out whether or not Brewster is able to spend $30 million in just 30 days, and how he manages to do it. (Spoiler alert: he finds out that it is much harder than one would think!)

Turn Your Movie Estate Planning Fantasies Into Reality

There we have it, eight movies that embody a theme of estate planning. Will you be adding any of these movies to your 2022 watch list? Were there any movies that you had already seen, and felt surprised to realize that they talked about estate planning? 

Hollywood movies can often take unrealistic, over-the-top takes on what an Estate Plan might look like, but they do bring about interesting hypotheticals that make viewers take a beat. If anything, they can show us that estate planning is anything but boring pieces of legal paper. To the contrary, estate plans are tied full of family history, legacies and emotion. 

If you feel inspired to create or update your Estate Plan based on what you’ve seen, know that we’re here to help! You can easily set up your own Trust or Will through our online services today. Click here to get started.

More of a fan of television shows? Don’t worry, we’ve got you covered! Check out our list of top television shows about estate planning here.

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