From Philip Seymour Hoffman and Heath Ledger to Frank Sinatra and Elizabeth Taylor, Hollywood’s dearly departed have taught us a lot about estate planning over the years.

Forbes put together a list of those lessons last year, demonstrating how creative and chaotic estate planning can be in the spotlight of fortune and fame. That had me thinking — it isn’t only the stars themselves who impart insight on the prudence of planning. Sometimes their movies do too.

Here’s a look back at a few of the greatest movies to put estate planning front and center (or at least in the middle of a juicy plot twist):

Cover of "The Aristocats (Special Edition...

Cover of The Aristocats (Special Edition)

  • The Aristocats (1970) — When you think about complex legal concepts, Disney animated features aren’t the first things that spring to mind. Nevertheless, The Aristocats offers a textbook illustration of the classic “life estate with remainder in fee simple absolute” — in other words, an elderly widow who leaves her entire estate to her cats, with the remainder to pass to her butler after the cats die. Unfortunately, the criminally inclined butler isn’t eager to wait that long…
  • The Descendants (2011) — George Clooney plays an attorney and the sole trustee for a massive family trust containing 25,000 acres of beautiful Hawaiian land. A series of accidents and unfortunate timing force his enormous family to wade through the murky waters of wills & trusts. Most interestingly, the whole plot revolves around “The Rule Against Perpetuities” (a pesky legal rule that limits some people’s future interest in property if too much time passes before the interest vests). Notably, both Hawaii and Massachusetts have adopted the same uniform version of “The Rule Against Perpetuities.”
  • The Grand Budapest Hotel (2014) — Nominated for Best Picture at this year’s Academy Awards, Hotel’s haywire plot is anchored in a controversial bequest. When an older woman dies, she leaves a very valuable painting to her much, much younger lover. Naturally, her ne’er-do-well children are less than thrilled. They challenge the validity of her will, and while that proceeding plays out with a little more madcap action than most of the real-life cases I’ve seen, it’s a great showcase for how easily miscommunication and strife can muddle an estate plan.

In Hollywood as in real life, estate planning is a potential breeding ground for epic drama — no wonder it’s a favorite topic in the screenwriting world! Of course, most of the movies’ great estate capers could have been avoided with careful planning.

What did I miss? If you have any favorite films with a focus on estate planning, please feel free to share them. And should any of these cinematic classics spark a question about your own estate plan, don’t hesitate to give me a call.

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