Everyone knows estate planning is important. It’s the cornerstone of protection when it comes to your legacy and loved ones. While many people only associate estate planning with the ultra-wealthy or elderly, the topic is a lot more prevalent in all of our lives than you think! (And these well-known shows, movies, and podcasts prove exactly that).
So, what are our favorite famous and noteworthy cinematic references to the topic of estate planning? Let’s dive in and take a look at our top contenders. You can find many of these movies, shows, and podcasts plus more on Apple TV or your preferred streaming service.
Best estate planning movies
The only thing we love better than good movies are good movies about estate planning. Whether they’re slapstick funny, need-a-box-of-tissues tearjerkers, or dark and twisted tales, these movies all struck a chord with us. You've probably heard of these major motion pictures, but did you realize they were related to estate planning?
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. Complete with endless twists, complicated family dynamics, and a dramatic reading-of-the-Will scene, this film has it all. Watch Knives Out if you want to see estate planning conflicts play out in a fresh, engaging way.
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.
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.
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.
The Descendants (Rated R): In full transparency, including the dramatic comedy The Descendants here may or may not have as much to do with George Clooney being the star of the flick as it does the storyline. As Trustee of the King Family Trust, which includes and controls 25,000 acres of island land, Clooney’s character shows the complexities of family dynamics that sometimes play out after the death of a loved one. The film follows Matt King as he tries to navigate what will happen at the end of the seven years, when the Family Trust is set to expire. Will they all agree to sell their precious land? You’ll have to watch to find out! We can assure you, as so many things are when it comes to family, it’s complicated!
Little Big League (Rated PG): When 12-year-old Billy‘s grandfather passes away, he hilariously becomes the owner of Major League Baseball’s the Minnesota Twins. Although it’s definitely not factually realistic, as a minor would never in real life gain a controlling share of an MLB team, it’s a family-friendly, funny flick that’s worth the watch, sure to entertain kids and adults alike!
Rain Man (Rated R): Tom Cruise and Dustin Hoffman proved to be a dream team when they came together to portray the complicated, funny, sad and sweet relationship of Raymond, an autistic older brother (played by Hoffman), and his younger, hotshot, go-getter brother Charlie (played by Cruise). When their estranged father leaves a multi-million dollar estate to a mental institution, Charlie decides to try and gain custody of Raymond in an attempt to get his hands on the money. This movie hits all the big themes of estate planning: Guardianship, Conservatorship, Trusts and Beneficiaries. It’s golden!
Best estate planning shows
Don’t think that we have all the time in the world to just sit around watching movies all day long. Binge watching shows is right up our alley, too! Some of our favorite series? You guessed it… those that deal with estate planning on some level. Check out some of the shows we love.
Downton Abbey: There may not be a better show out there about estate planning than Downton Abbey, which aptly explores the succession line of the British Crowley family. From season one’s sinking of the Titanic, all the way through the subsequent five seasons that follow, with no male heir to legally receive the estate of Downton Abbey, the series is as enthralling as it is engaging.
Succession (Seasons 1-3): OK, yes, we did just say that Downton Abbey might be the best show out there about estate planning. But we’re doubling down here with HBO’s Succession. The drama is an estate-planning must watch. It’s in the title! Logan Roy is the patriarch of the family and the Waystar company, while his adult children Kendall, Shiv, and Roman battle to become their father’s successor. To make matters worse, it seems as though Logan may be getting some twisted enjoyment out of pitting his children against one another. Logan is aging and deals with health issues throughout the show, leaving viewers to beg the question of why he hasn’t made a decision and drawn a line in the sand. Why hasn’t Logan publicly named a successor? Is there something in his Trust, Will, and business succession plan that he’s scheming but hasn’t divulged? Has he orchestrated these political struggles to see which child will eventually come out on top as the worthy successor of the multi-billion dollar empire? Join in on the diabolical fun!
Insecure (Season 2): Insecure is a comedy series created by and starring Issa Rae. Issa and Molly are two best friends living in Los Angeles, and the series follows their unique story arcs as they deal with their own flaws, insecurities and challenges. This is all the while trying to embrace adulthood in their 30s, navigating awkward situations, keeping true to one’s own identity, and understanding what it means to be a black woman today. This show is not only hilarious and highly relatable, it touches on an important variety of social and racial issues and is a creative commentary on the black experience. Season two also relates to Molly and her aging parents. As an attorney, she finds it pressing that her parents establish an estate plan. The show portrays one of the most realistic and relatable depictions of what it’s like for a Millennial who is worried about their parents. It is around this age that we begin to realize that our parents won’t live forever. At times, they need to “parent up,” when their parents are not ready to face this reality themselves. The series does an excellent job of depicting this narrative. Ultimately, Molly succeeds by encouraging open and honest conversations and enlisting the help of an expert.
A Series of Unfortunate Events: Tune into A Series of Unfortunate Events if you have a preference for fantasy. This Netflix-adaptation of the children’s classic stars Neil Patrick Harris, but not in the way you’d imagine. He portrays the diabolical Count Olaf, who is named the guardian of the Baudelaire orphans: Violet, Klaus and Sunny. The orphans are investigating their parents’ mysterious death, yet they are continuously interrupted by Count Olaf’s vicious attempts to get his hands on their inheritance. Luckily, the smart children foil Olaf’s plans at every twist and turn, outsmarting him each step of the way. Although the story takes place in a fantasy world, and with imaginary laws, the takeaway is very real: an ineffective estate plan can create a world of trouble.
Modern Family - Season 8’s "Ringmaster Keifth:" While the entire series doesn’t directly reflect estate planning themes (although ultimately any well-developed show about a family could find many opportunities to touch on the topic), there is one episode we find particularly on-brand. Modern Family’s “Ringmaster Keifth” episode in season 8 shows Jay and Gloria‘s struggle to come to a decision about who they should name as guardian for their son, Joe. As they imagine what it could look like should either of Jay’s adult children and their spouses raise young Joe, we dare you to not laugh.
Best estate planning podcasts
Not everyone is a visual or textbook learner. Not only can it be hard to sit and focus on content delivered in a written or video format for extended hours, but not many of us have the time. In case you’re feeling super busy but are feeling up to a bit of multitasking, may we suggest hitting “play” on a podcast? Here are our top picks for estate planning podcasts. Each one is intended to suit the needs and interests of different groups of listeners, so we hope that you find the perfect one for you!
Estate Planning Strategies: Estate Planning Strategies is one of the more well-rounded podcasts for those wanting to learn anything and everything about estate planning. This is a dedicated podcast that discusses topics such as Wills, Trusts, guardianship, and power of attorney. They also focus on how to build a legacy. This includes tips on how to create wealth, protect assets, and understand the myriad of taxes that could affect your estate. If there’s any topic related to estate planning, this podcast is sure to be discussing it.
What’s Your Legacy: What is your legacy? This is a big, open-ended question that makes people stop in their tracks and think. More often than not, this is the big question that helps individuals really start to take their estate planning seriously. After all, you can’t leave behind a lasting legacy without a plan. Join Galem Girmay on What Is Your Legacy? as she explores the concept of a legacy. She invites spectacular guests on the podcast, and together they discuss the different shapes that legacies can take, as well as the complex emotions that come along with it.
Complete Estate Planning: “Do you know what will happen to your loved ones when something happens to you?” Cincinnati-based attorney Nick Rosenbauer, host of Complete Estate Planning poses this important question. If you don’t know the answer, or don’t like your own answer, to this question, then perhaps you should give this show a listen. Nick enables listeners to learn about how to go about protecting a family legacy by leveraging the act of estate planning. A wide range of topics are explored in each episode, such as how to plan for a child with special needs, or how to include your Facebook or Bitcoin (digital assets) in your estate plan.
Life Planning 101: Last but not least is Life Planning 101. Host Angela Robinson shares over 40 years of experience to help listeners with a broad range of estate planning and related topics, including planning your finances, investments, taxes, and retirement. If you consider yourself an all-around planner, then this show could be perfect for you. Consider this podcast the perfect planning lifestyle complement to one of your other estate planning podcasts. For instance, she covers topics such as charitable gifting, how to combat inflation, and how to save for your grandchildren.
Estate planning doesn’t have to be just dark and depressing. Clearly, there are qualities to the topic that lend to our entertainment. And when they’re good enough to show on the big screen or to be discussed on a podcast, they’re often good enough for us! Consider adding these movies, shows, and podcasts to your list to get some estate planning inspiration.
That said, we know not everyone thrives on the real-life estate planning issues that need to be dealt with. Looking for help? We’ve got your back - reach out today to find out how Trust & Will can help you navigate the process and set up an Estate Plan that’s designed specifically for your family and your legacy.
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