[10] Holly's acting career began at the age of 20 when she appeared as Carla Walicki in two episodes of Hill Street Blues.

At age 23, she joined the cast of the ABC television soap opera All My Children as Julie Rand Chandler (1986–1989).

She portrayed the comic book character Betty Cooper in the TV movie Archie: To Riverdale and Back Again in 1990.

In 1992, Holly's big break came when she was cast as small-town Deputy Sheriff Maxine Stewart opposite veteran movie actor Tom Skerritt on CBS's Picket Fences for four seasons, appearing in every episode except one.

She was a member of the cast of NCIS as Director Jenny Shepard from 2005 to 2008, reuniting with her former Chicago Hope co-stars Mark Harmon and Rocky Carroll.

Holly portrayed the "worldly and stunning"[11] lead medical examiner Dr. Betty Rogers, a regular character on the CTV series Motive.

Although he was only 14 when he died, he had traveled extensively in Europe and Central America, lived in New York City and Los Angeles, and these experiences produced in him a fascination for architecture and archaeology.