Holland Virginia Taylor was born in Philadelphia, Pennsylvania. She is the youngest of three daughters born to Virginia, a painter, and C. Tracy Taylor, an attorney. During her teenage years in Allentown, Taylor earned the nickname "Penny Taylor" due to the coppery hue of her hair. She attended Quaker schools and later pursued a drama degree at Bennington College, where her passion for acting took root.

Career Beginnings and Breakthrough

At the age of 22, Holland Taylor moved to New York City with aspirations of building a career on the stage. Despite years of setbacks and near-misses, her dedication paid off when she landed the role of Ruth Dunbar in the 1980 television sitcom Bosom Buddies, co-starring a then-unknown Tom Hanks. The show marked her breakthrough in television and opened doors to subsequent opportunities in both comedic and dramatic roles.

Television Success and Recognition

One of Taylor’s most acclaimed performances came in the ABC legal drama The Practice, where she portrayed Judge Roberta Kittleson. Her work on the series earned her the 1999 Primetime Emmy Award for Outstanding Supporting Actress in a Drama Series.

She gained further popularity for her role as Evelyn Harper, the witty and opinionated mother on the CBS comedy sitcom Two and a Half Men. Her performance on the show was widely praised for its comedic sharpness and consistent delivery across multiple seasons.