Holland first came to the public's attention as the colorful, brassy boss of Tom Hanks and Peter Scolari in the ahead-of-its-time "Bosom Buddies" (ABC, 1980-82). Often the highlight of network fodder like "Me and Mom" (ABC, 1985), "Harry" (ABC, 1987) and "Going Places" (ABC, 1990-91, which reunited her with "Bosom Buddies" executive producers Thomas L. Miller and Robert L. Boyett), she was hilarious as the imperious and ambitious political wife of John Forsythe in Norman Lear's "The Powers That Be" (NBC, 1992-93). Following her stint as recurring character Dean Susan McCann on the Saturday morning sitcom "Saved By the Bell: The New Class" (NBC, 1993-95), Holland fared well in support of the wonderfully daffy Tea Leoni, playing an overbearing, boisterous tabloid editor/reporter on the sitcom "The Naked Truth" (ABC, 1995-96; NBC, 1996-98). Her biggest splash, however, came for David E Kelly as the unabashedly sexy, middle-aged judge Roberta Kittelson on ABC's "The Practice" in 1998. Originally tagged for a one-shot guest appearance, Taylor was so impressive; she was signed on in a recurring capacity and netted a Best Supporting Actress Emmy for her work. (Ironically, she beat out the favored Nancy Marchand, opposite whom she frequently appeared on stage and screen.) Her increased exposure on "The Practice" helped her land plum roles as Judd Nelson's ailing mother in the Fox Family Channel's remake of "The Spiral Staircase" and as a super-cynical advisor to Randy Quaid's President in ABC's "Mail to the Chief", the two movies airing on back-to-back days in April 2000. Immediately following "The Practice" the actress' TV success continued unabated when she landed the role as Charlie Sheen and Jon Cryer's self-absorbed mother Evelyn Harper on the hit sit-com "Two and a Half Men" (CBS, 2003 - ).

Years after making her feature debut as a TV interviewer in "The Next Man" (1976), Taylor delivered memorable portrayals as Kathleen Turner's book publisher-friend in "Romancing the Stone" (1984) and its sequel "The Jewel of the Nile" (1985) and also turned up in John Hughes' "She's Having a Baby" (1988, as Kevin Bacon's mother) and Woody Allen's "Alice" (1990), though her big screen roles remained few up until 1995. That year the busy Taylor appeared in flashy supporting roles in four films: as Nicole Kidman's mother in "To Die For"; as Andy Garcia's bohemian adoptive mother in "Steal Big, Steal Little"; as Mrs. Rubens in "How to Make an American Quilt"; and as Viveca Lindfors' actress daughter in Henry Jaglom's ensemble comedy/drama "Last Summer in the Hamptons". Since then, the never-married Holland has played mother to Leslie Mann's Ursula in "George of the Jungle" and Jim Carrey's Truman Burbank in "The Truman Show" (both 1997). Her filmmaker nephew Brad Anderson cast her as Hope Davis' urbane, matchmaking mother in "Next Stop, Wonderland" (1998) and as Marisa Tomei's unpredictable shrink in the Sundance-screened "Happy Accidents" (2000). Later that year, Taylor was memorable as an elegant temple member who wants the young rabbi (Ben Stiller) to date her TV anchor daughter in "Keeping the Faith.” She then segued to play another accomplished career woman as Reese Witherspoon's professor in the hit comedy "Legally Blonde," and adroitly essayed First Lady Nancy Reagan for the well-received cable telepic "The Day Reagan Was Shot" (2001). In 2002, Taylor was cast as Grandma in the family-adventure feature, "Spy Kids 2: The Island of Lost Dreams," a role she reprised in the next sequel "Spy Kids 3-D: Game Over" (2003).

Meanwhile, television continued to provide the best showcase for the actress' versatile talents. From 1998 to 2004 she had her best, most multifaceted role yet in the form of Judge Roberta Kittleson on the David E. Kelley-created ABC legal drama "The Practice," a character that allowed to explore many sides of a strong woman in a position of authority who also had real, human foibles--Taylor also carried the character over to an episode of Kelley's dramedy "Ally McBeal.” On the cable series "The Lot" (AMC, 1999-2001), she was winning as Letitia DeVine, the often tipsy, Hedda Hopper-esque Old Hollywood gossip queen who set the stage for each episode. Her next stint as the grandmother of a talking infant on CBS's ill-conceived "Baby Bob" (2002) was mercifully brief, allowing her to find another pitch-perfect role on the hit CBS sit-com "Two and a Half Men" (2003 - ) as the Evelyn Harper, the critical, shallow, self-obsessed, Botox-loving mother of brothers Charlie Sheen and Jon Cryer. An instant hit with audiences and critics alike, Taylor took home her second Emmy in 2005 for Outstanding Supporting Actress in a Comedy Series.

Having perfected playing the blithely disapproving matriarch, Taylor nabbed another such role in the romantic comedy "The Wedding Date" (2005), playing Debra Messing's mother. The actress remained most popular, however, for her work on television. In 2007, Taylor once again received an Emmy nod her role as matriarch Evelyn Harper on “Two and a Half Men.”