Holland Taylor was born in Philadelphia, Pennsylvania, to her mother, Virginia (Davis),a painter, and her father, C. Tracy Taylor, an attorney, as the third-born and last daughter. She spent her teenage years in nearby Allentown, Pennsylvania, where she earned the nickname "Penny Taylor" due to her distinctive coppery hair color.
Taylor attended Quaker schools before majoring in drama at Bennington College. At the age of 22, she moved to New York with the ambition to become a "great big Broadway star." After 15 years of "disappointments and near-misses" in New York and California, Taylor landed the role of Ruth Dunbar in the sitcom Bosom Buddies (1980) alongside Tom Hanks, which marked her "breakout" role.
This breakthrough led to numerous TV and film offers, including the movie Romancing the Stone (1984),where she played Kathleen Turner's book publisher and friend. Initially hesitant to accept the role, Taylor's acting coach and mentor Stella Adler encouraged her to take the part, advising her not to be too "stage-minded."
In 1992, Taylor was still residing in Greenwich Village, New York, and commuting between a rented apartment in Hollywood and New York to work on both coasts. Although her first love was the theater, Taylor found the work in TV and films to be more lucrative. However, by 1992, she was struggling to cope with the constant travel, admitting she was "dealing with it less and less well."
Over the next few years, Taylor relocated to California full-time. In the last couple of years, she sold her apartment in West Hollywood and moved into her own home in the Hollywood Hills. Taylor's hard work paid off when she won an Emmy in 1999 for her work in The Practice (1997).