When actress Jennifer Tilly and Simpsons co-developer Sam Simon divorced in 1991, Tilly received 30 percent of Simon’s future proceeds from his fledgling animated sitcom. But does she get to sleep in a racing car?

An Oscar-nominated actress and a veteran of TV comedy, Tilly is so much more than yet another pampered Hollywood divorcée to grace the cast of The Real Housewives of Beverly Hills. Tilly regularly played smaller parts in film and television throughout the 1980s, and, following her split from Simon, she broke through with a critically acclaimed performance in Woody Allen’s 1994 black comedy Bullets Over Broadway. From there, Tilly’s film and TV career exploded, and she even made a name for herself competing in the high-stakes world of professional poker, winning a coveted World Series of Poker bracelet in 2005.

But despite Tilly’s good fortune, no gamble ever paid off better for the actress, poker...