Kirstie Alley– 69 – $40 MILLION

Throughout her childhood, actress Kirstie Alley lived a modest life with her parents. However, around halfway through college, Alley decided to drop out and began pursuing a career of her own. While working as an interior designer, Kirstie appeared on game shows like Match Game and Password Plus. And after winning her fair share of prizes, Kirstie then used them as investment money to help her transition into the world of acting.

Her film debut was in 1982 with the classic sci-fi film Star Trek II: The Wrath of Khan. After starring in a few other movies, the actress earned widespread acclaim portraying Rebecca Howe in the TV series Cheers – she earned an Emmy Award and a Golden Globe for the role. Alley has been married twice. She has married high-school sweetheart Bob Alley in 1970, and the couple divorced in 1977. Alley married actor Parker Stevenson on December 22, 1983. The couple adopted son William in 1992 and adopted daughter Lillie in 1995. The marriage ended in 1997.