Jennifer Tilly, like many professionals, began acting in high school, having been bitten by the theater bug as a teen. Her mother, a former stage actress herself, helped Jennifer (as well as her younger sister Meg) pursue walk-on roles and supporting parts in various Hollywood TV shows, and Tilly made her TV debut on an episode of the sitcom “Oh Madeline” in 1983. In 1984, she secured a regular role on the obscure comedy series “Shaping Up,” which starred Leslie Nielsen as a grumpy health club owner. Tilly appeared in all five episodes. Her real big break came that same year, as she secured a recurring role on the hit cop show “Hill Street Blues,” appearing in six episodes. 

Tilly would spend the next few years acting in guest spots on hit shows like “Moonlighting,” “Cheers,” and “Remington Steel.” She would also make a move into cinemas, appearing in multiple studio comedies and thrillers. In the ’90s, her profile only continued to rise, and she even secured an Academy Award nomination for her performance in Woody Allen’s 1995 film “Bullets Over Broadway.” In 1996, she became a legit queer icon thanks to her role in the Wachowski’s lesbian heist thriller “Bound,” and in 1998, she became an indelible scream queen thanks to her role in “Bride of Chucky.” There’s nothing Tilly hasn’t done. 

She’s also, as it turns out, blindingly rich. As it happens, the above-mentioned “Shaping Up” was co-created and produced by ultra-producer Sam Simon, one of the men behind “Taxi” and “Cheers.” Tilly and Simon definitely hit it off, because they wed in 1984. They were married for six years, divorcing in 1991, while Simon was deeply entrenched in the production of “The Simpsons.” 

As it happens, one of the stipulations of the divorce was that Tilly received 30% of Simon’s proceeds from “The Simpsons” for as long as he was a credited producer. Tilly, decades later, is still getting money. She talked about it in a recent interview with E!

Tilly is currently appearing as herself in “The Real Housewives of Beverly Hills,” and she is a professional poker player who was inducted into the Poker Hall of Fame in 2022. Her wealth isn’t terribly well-known to the public, although one of her “Real Housewives” co-stars did spot the fact that she carries a Louis Vuitton purse that’s worth about $33,000. To E!, she noted: 

“My ex-husband was Sam Simon, who created ‘The Simpsons.’ […] I was married to him for seven years, and we were together for about 10 years. And then, when we got divorced, I got a piece of ‘The Simpsons’ in the divorce settlement, and nobody knew that ‘The Simpsons’ was going to go on for trillions of years. […] So every day, honestly, every day I’m like, ‘Thank you, Sam!'”

The actual percentage of her divorce settlement was something she revealed in the podcast “The Originals with Andrew Goldman.” She said that her take was about a third of Simon’s salary. 

Simon, it should be noted, was only actively helping produce “The Simpsons” from its inception in the late 1980s through the year 1993 when he left the show. Simon himself revealed to Marc Maron on his “WTF” podcast, that he negotiated a deal when he left that he retains an executive producer’s credit in perpetuity and that he gets a cut of the show’s profits, especially as it pertained to home video. Even while not working on the show, Simon earned at least $10 million annually from it (although he also admitted to earning “tens of millions” at one point). A third of it went to Tilly. The irony that she also voices Bonnie Swanson on “The Simpsons” competitor “Family Guy” is not lost on us.

Indeed, even though Simon passed away in 2015, he still has his executive producer credit on “The Simpsons,” meaning Tilly is still getting money to this day. Tilly divorced Sam Simon 34 years ago, and his work is still paying the bills. We should be grateful that Tilly has continued to grace us with her presence on the big screen. She doesn’t need to work ever again.