Holland Taylor Through the Years: ‘Two and a Half Men’ to ‘The Morning Show’

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Holland Taylor Through the Years: Her Roles in ‘Two and a Half Men,’ ‘The Morning Show’ and More

Holland Taylor has had a steady career since landing the role of Denise Cavanaugh in the 1977 series The Edge of Night and earning her first Emmy Award in 1999 for her role in The Practice. Taylor’s first TV appearance was as Mrs. Arnold in J.T. and she made her first film appearance in 1976’s The Next Man. Her most notable roles, however, include Evelyn Harper in Two and a Half Men, Peggy Peabody on The L Word, Professor Elspeth Stromwell in Legally Blonde alongside Reese Witherspoon, Ellen Kincaid in Hollywood and Cybil Richards in The Morning Show. Taylor reflected on her long career on the “LGBTQ&A” podcast in 2020. “I’ve had an extraordinary career in that the usual plight of the actor, which is long periods of not working, has not been my situation,” Taylor shared at the time. “I’ve really worked pretty steadily. My beginning years were hard because I was too young to play the parts that I was right for … But once I hit my stride, I’ve never really had a hard period.” The actress turned 80 in 2023 but has never been busier. She talked with Advocate how life continues successfully for people entering their 80’s and even 90’s. “I just saw an article about Ridley Scott, who is 86 and whose new movie about Napoleon is just hitting theaters now. Same with Martin Scorsese who is in his late 80s and Clint Eastwood, who is in his 90s. They are both still directing,” Taylor told Advocate in December 2023. “I do believe that those of us over 80 continue to prove that we not only can do our jobs, but we’re good at them too!” Continue scrolling to see Taylor’s career in photos:

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1965 to 1967

Taylor debuted on Broadway in the 1965 production of The Devils and also appeared in Off-Broadway’s The Poker Sessions as Irene in 1967. She went on to star in Colette (1970), Butley (1972), We Interrupt This Program (1975) and Murder Among Friends (1975).

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1977 to 1980

Taylor landed her breakthrough television role as Denise Cavanaugh in The Edge of Night. She gained popularity by starring in the 1980s sitcom Bosom Buddies alongside Tom Hanks. 

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1984 to 1994

Taylor went on to star in Me and Mom (1985), Going Places (1990) and The Powers That Be (1992) alongside John Forsythe and David Hyde Pierce. In 1994, Taylor joined the cast of Saved by the Bell: The College Years as Dean Susan McMann, just episodes before its cancellation.

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1995 to 1998

Taylor portrayed newspaper editor Camilla Dane on the sitcom The Naked Truth. She was one of the few cast members to last through the show’s entire run until 1998. 

Taylor broke into the film scene and landed roles in How to Make an American Quilt (1995) with Winona Ryder, The Truman Show (1998) with Jim Carrey and Next Stop Wonderland (1998).

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1999

Taylor earned her first Emmy Award for Outstanding Supporting Actress in a Drama Series for her role as Judge Roberta Kittleson in The Practice. Her role was meant to be a one-time appearance, but Taylor remained a regular cast member from 1998 to 2003. 

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2000

The Baby Mama actress earned an Emmy Award nomination for Outstanding Guest Actress in a Comedy Series for her recurring role on AMC’s The Lot.

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2005 to 2010

Taylor starred as Evelyn Harper on Two and a Half Men alongside Charlie Sheen and Jon Cryer. She earned four Emmy Award nominations for Outstanding Supporting Actress in a Comedy Series between 2005 and 2010. 

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2011 to 2013

Taylor researched, wrote and produced a one-woman play about the late Texas governor Ann Richards titled Ann: An Affectionate Portrait of Ann Richards. The show opened in Chicago as a pre-Broadway engagement and played at the Kennedy Center from December 2011 to January 2012. It was then performed on Broadway the following year. Taylor earned a Tony Award nomination for Best Lead Actress in a Play for her performance.

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2016

In a November interview with WNYC, Taylor revealed she was dating a woman who was much younger than her.

“There’s a very big age difference between us which I’m sure shocks a lot of people, and it startles me. But as they say, ‘If she dies, she dies,’’ Taylor  joked at the time.

A month later, it was confirmed that Taylor was talking about fellow actress Sarah Paulson. 

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2017 to 2019

Taylor continued to appear in Kepler’s Dream (2016), Gloria Bell (2018) and Bombshell (2019). She also portrayed Ida Silver in the television series Mr. Mercedes based on Stephen King’s trilogy of the same name. 

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2020

Taylor played Ellen Kincaid in the miniseries Hollywood, earning an Emmy Nomination for Outstanding Supporting Actress in a Limited Series or Movie.

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2021 to 2023

Taylor reunited with Witherspoon and started working with Jennifer Aniston and Steve Carell in The Morning Show playing the role of Cybil Richards. The series was renewed for a fourth season in September 2023, just ahead of the season 3 premiere. She also appeared in 2023’s Billions as Dr. Eleanor Meyer.