Jennifer Tilly Scored Big In Her Divorce Settlement With Sam Simon

Jennifer Tilly and television producer Sam Simon tied the knot in 1984, but by 1991, they called it quits. Tilly didn't just walk away with a hefty divorce settlement — she also kept Sam as a friend for years until he ultimately died in 2015 after being diagnosed with terminal colon cancer two years before. The producer was known for being a showrunner on the sitcom "Taxi," a writer on "Cheers," and one of the developers on the early seasons of "The Simpsons." At the time of his death, he was reportedly worth $100 million. 

Leading up to his death, Simon and Tilly continued to spend time together. "Probably, my social life is more active than it's ever been," he told Vanity Fair in 2014 after being diagnosed with cancer. "And that's because of my fine choice in women throughout my life." The "Bride of Chucky" actor told the outlet how her ex-husband had changed for the better since learning he was terminal. "He's discovered what's important in life," Tilly said. For decades before he was sick, Simon was very active in charitable endeavors, and those efforts only increased after his diagnosis. "I think it's really nice for him that he's doing it now and he gets to see the results of his philanthropy," Tilly told The Hollywood Reporter in 2013 when discussing her ex-husband. In fact, Simon told the outlet he planned to give his fortune to charity once he died.

A bulk of that fortune was residuals from "The Simpsons." Thanks to their divorce settlement, Tilly was paid handsomely from those earnings over the years. 

In 2007, a profile of Sam Simon on "60 Minutes" revealed the TV producer was still raking in money from his work on "The Simpsons," even though he had stepped away from the show in 1993. The program reported that Simon made $10 million a year from the animated series and that a chunk of that was paid out to Jennifer Tilly because of the former couple's divorce settlement. A couple of years later, Simon set the record straight and said during a 2008 interview with Stanford Magazine that his earnings from the show were underreported and were closer to "tens of millions" per year.

While the exact amount of Simon's "The Simpsons" annual residuals is unknown, there's no doubt that it's a substantial sum. Due to a favorable divorce settlement, Tilly took home one-third of those earnings. The "Bullets Over Broadway" actor discussed how this gave her freedom in Hollywood. "I used to do a lot of movies because the roof was leaking or to pay for the plumbing, and now I don't have to," she said while appearing on "The Originals" podcast in 2021.

For years, acting took a backseat to poker for Tilly — who played professionally — but she decided to rededicate herself to the craft. "I'd thought, I'm so past that where I need validation from strangers. But I realized, no, I really do need validation from strangers," she explained. It is also worth noting that her income from Simon changed following his death.

When Sam Simon died in 2015, there were a couple of discrepancies over his $100 million estate and what was owed to the women in his life. Both Jennifer Tilly and Kate Porter — who was romantically involved with Simon at the time of his death — filed claims against the famed TV producer's estate, according to TMZ. Porter claimed that Simon had asked her to quit working and offered her $5 million if she did so, but was not compensated after he died. "Those entrusted with overseeing the Estate of Samuel Simon, and carrying out his last wishes, are in fact betraying that trust and refusing to honor the commitments made before he passed away," Porter's lawyer said in a statement obtained by The Hollywood Reporter in 2016.

Meanwhile, Tilly had filed a claim against her ex-husband's estate in 2015. A couple of years later, the "Seed of Chucky" star reached a settlement on the matter. Instead of being paid around one-third of his ongoing earnings from Fox — the network that produces "The Simpsons" — Tilly was given a lump sum. "Because of Sam's death, it was no longer practical for Jennifer, Sam and Coconino [Simon's company] to follow the procedure that Jennifer had been following with Sam and Coconino from 1993 until Sam's death," court documents from 2017 read, as reported by Radar.

Even though the annual checks stopped, Tilly still made out well financially once her ex-husband passed.