If a genie granted you three wishes, odds are you’d start big: unlimited wealth, eternal youth, and maybe a private island. In case the genie is a stickler for realism, here’s a more achievable wish: make me as wealthy as Jennifer Tilly.
Yes, that Jennifer Tilly — Oscar-nominated actress, poker pro, and possessor of a voice so distinctive you could pick it out in a hurricane. She may not be Bezos-rich, but she’s the kind of rich where you can say things like "I think I’ll buy a vineyard" without blinking.
Another reasonable wish is “Make me as effortlessly charming, funny, and generally well-liked as Tilly.” But we’re not here to talk about Ms. Tilly’s many enviable qualities. We’re going to focus on just one: her remarkable success in turning divorce into a financial jackpot.
Jennifer Tilly: More than an alluring, distinctive voice
Jennifer Tilly has made a name for herself, from stealing scenes in Bullets Over Broadway to bluffing her way to victory at the World Series of Poker.
However, in a twist worthy of a Hollywood rom-com-meets-legal-thriller, it turns out Tilly's most impressive payout didn't come from her acting gigs or poker hands; it came from her divorce settlement.
More on divorce settlement: Divorce settlement agreements: FAQs and some words of non-advice
How one divorce deal beat the house
Jennifer Tilly was married to Sam Simon, the late, great co-creator of The Simpsons. They tied the knot in 1984, split in 1991, and somewhere in the fine print of that divorce decree lay the golden ticket. That ticket is a cut of The Simpsons royalties.
Simon, as it turns out, was not only brilliant but also absurdly successful. Even after leaving The Simpsons in 1993, his estate continued to rake in between $20 million and $30 million a year. Thanks to their settlement, Tilly reportedly receives 30% of those net proceeds.
Quick math: that’s somewhere between $6 million and $9 million a year.
Every year. Since 1991.
Tilly herself has commented on the surreal nature of this arrangement, quipping on The Real Housewives of Beverly Hills that the show will go on for "trillions of years." And at this rate, it might.
Thanks to the enduring success of The Simpsons (merch, syndication, international rights, and now streaming deals), Tilly’s settlement continues to be the kind of passive income most people only dream about. While her career flourished in its own right, this legal agreement has arguably been the most consistently lucrative hand she’s ever played.
What we can learn from Springfield's richest ex-wife
Before you go drafting your own divorce papers in search of cartoon gold, listen up. People who do not resemble Jennifer Tilly won’t be negotiating over globally syndicated animated empires. But the core principle still applies: asset division matters.
In Washington State, the law views most assets acquired during a marriage as community property. That means they’re up for division when things go south. And while your ex may not be the next Matt Groening, retirement accounts, business interests, royalties, and investment income can all play a role.
Jennifer Tilly’s story highlights the importance of understanding what you’re entitled to and thinking long term. A good settlement isn’t just about today’s value but about the future’s potential.
It’s worth noting that despite walking away with a slice of Springfield, Jennifer Tilly and Sam Simon remained unusually friendly post-divorce. Not the "we’re cordial for the kids" kind of friendly, but the kind where she cared for him during his battle with cancer. She’s publicly spoken about their close bond, and it seems they truly did part ways with both dignity and dividends intact. A divorce that ends in both friendship and fortune? That is what we call the unicorn of family law.
Meanwhile, Tilly’s cartoon-fueled cash flow has granted her the luxury of pursuing only the roles that truly speak to her, which apparently include several turns in the Child’s Play franchise. Yes, that one with Chucky, the homicidal doll. To be fair, horror fans are loyal, and nothing says financial freedom quite like being able to pick your projects based on whimsy rather than rent.
Get the advice, not just the alimony
Jennifer Tilly may not consider herself rich, but if receiving millions a year from a single line in a divorce agreement doesn’t qualify, we’d hate to see what does.
Take it from her: the right legal guidance during a divorce can set you up for long-term financial peace of mind, or at least help you avoid feeling like you lost an episode of Judge Judy.
If you're going through a divorce or just want to know your rights, we're here to help. We may not get you a Simpsons-level payout, but we’ll make sure you don’t leave the negotiation table empty-handed. Give us a call.