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Richardson began as the understudy for the role of Gypsy Rose Lee in Angela Lansbury's Broadway production of Gypsy: A Musical Fable in 1974, also playing several small chorus parts. In the next ten years she worked in regional theater, commercials, and other Broadway and Off- Broadway plays. She had roles in programs such as The Equalizer, Spencer For Hire, and Kate & Allie. She appeared in one episode of The Cosby Show in the third season with her real-life husband, playing a woman giving birth to her ninth child. Richardson also appeared in the films Christmas Evil and C.H.U.D.. In 1989, she appeared in one episode of Quantum Leap as a radio station owner.
In 1983, she left New York for LA briefly to do a sitcom centered around Katey Sagal's twin sisters, Liz and Jean Sagal, called Double Trouble, for Norman Lear. When asked to go back and do a second season after her contract had expired, she passed in order to stay in New York and continue performing in Beth Henley's The Miss Firecracker Contest off-Broadway. A few years later Allan Burns, who co-created The Mary Tyler Moore Show, brought her back to Los Angeles to star in two sitcoms he produced: Eisenhower and Lutz and FM. Both shows ran for 13 episodes.
In 1991, three months after giving birth to twins, Richardson became a last-minute replacement for Frances Fisher in what would be her breakout role as Jill Taylor on the ABC sitcom Home Improvement. Richardson received four Emmy nominations, and two Golden Globe nominations in this role. While working on Home Improvement, she hosted the Emmys with Ellen DeGeneres, starred in the miniseries Undue Influence with Brian Dennehy, Sophie and the Moonhanger on Lifetime with Lynn Whitfield, and earned an Independent Spirit nomination in 1997 for her first major theatrical film role in Ulee's Gold.
In 2002, Richardson replaced Janine Turner in the Lifetime medical drama series Strong Medicine, as a new character, Dr. Andy Campbell. She was nominated for two Prism Awards for her work in Strong Medicine. After three seasons on that show, she was cast in a recurring role as Sheila Brooks, campaign manager for Republican presidential candidate Arnold Vinick (Alan Alda) in the final two seasons of NBC political drama The West Wing.
Richardson appeared in the first season of Law & Order: Special Victims Unit. In 2008, she was the executive producer of the video documentary Long Story Short, which tells the story of Larry and Trudie Long, a popular Asian American nightclub act of the '40s and '50s, told through the eyes of their daughter and her friend, actress Jodi Long. In 2010, she appeared in an NBC made-for-TV film, The Jensen Project, and in 2011, she appeared in the Lifetime television film Bringing Ashley Home, also starring A.J. Cook and Jennifer Morrison. In 2012, she starred in the coming-of-age film Beautiful Wave and in the following year appeared in the Hallmark Channel TV film Smart Cookies. Since then, Richardson has filmed several small independent films and two more movies for the Hallmark channel, Friend Request and Snow Bride.
On the twelfth episode of the fourth season of Last Man Standing titled "Helen Potts", Richardson guest-starred as the titular character and reunited with her former Home Improvement co-star, Tim Allen. At the end of the episode, it was revealed that one of her sons' name is Randy, who was portrayed by her other Home Improvement co-star; Jonathan Taylor Thomas. She returned as Helen Potts in the next season.
In 2015, she ran for the position of national president of the SAG-AFTRA, after she had served on the board for one term. She lost the election narrowly to incumbent President Ken Howard. She was re-elected to the National and Local Los Angeles Boards of SAG-AFTRA.
In 2016, Richardson returned to the stage in Steel Magnolias at the Bucks County Playhouse in New Hope, Pennsylvania. This production was directed by four time Oscar nominee Marsha Mason, and also starred Elaine Hendrix, Lucy DeVito, Jessica Walter and Susan Sullivan. On June 9, 2016, this production became the highest-grossing show in the history of the Bucks County Playhouse.