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Sheryl Ann Fenn was born in Detroit, Michigan, in 1965. Her family came from a rich ancestry of Italian, Irish, French, and Hungarian descent. Both of her parents are musicians. Her mother, Arlene Quatro is a keyboard player, while her father Leo Fenn, managed rock bands.

During her teenage years, Fenn decided to drop out of school to pursue acting. She then decided to enroll at Lee Strasberg Theatre Institute in Los Angeles.

Fenn began her career as an actress by starring in low-budgeted films. She made her film debut in a comedy-drama film The Wild Life in 1984 as Penny Harlin. She also starred in other 1980s films, including Just One of the Guys, Thrashin’, and Zombie High.

In 1988, Fenn starred on her first lead role in the erotic drama film Two Moon Junction. Four years later, she got her breakthrough in the film adaptation of Of Mice and Men in 1992. She played the role of a country wife, a complete opposite of what she typically plays.

Since then, Fenn appeared in several films, such as Just Write, Novel Romance, and Treasure Raiders.