ALLY SHEEDY

Born in 1962, Ally Sheedy looks flawless as she ages. She made her film debut with the movie Bad Boys, and her career went uphill from there. Aside from the first film she worked with, she also starred in The Breakfast Club and St. Elmo’s Fire.

Even with her successful projects, she might not have been able to set aside investment money that could have helped her have a worry-free retirement. At the rate of where she was then, Sheedy probably lived a stress-free life. She got addicted to prescription medication, which could have eventually lead to a lurking bankruptcy.