Exploring Holland Taylor's Career Journey: From 'Two and a Half Men' to 'The Morning Show' and Beyond

Holland Taylor's career has been consistent ever since she landed the role of Denise Cavanaugh in the 1977 series The Edge of Night and won her first Emmy Award in 1999 for her performance in The Practice.

Her first television appearance was as Mrs. Arnold in J.T. and she made her film debut in 1976's The Next Man. Some of her most memorable roles 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 looked back on her extensive career during an episode of the "LGBTQ&A" podcast in 2020.

Sharing her thoughts, Taylor mentioned, "I've been fortunate to have a remarkable career where I haven't faced the typical struggle of actors with long periods of unemployment. While the early years were challenging due to age restrictions on roles, once I found my groove, I've enjoyed consistent work without any major setbacks."

The actress, who turned 80 in 2023, is as busy as ever. In a conversation with Advocate, she shared how people in their 80s and 90s can still thrive.

She mentioned Ridley Scott, Martin Scorsese, and Clint Eastwood, all in their 80s and 90s, who are still actively directing. "We over 80 continue to show that we can excel in our work and be successful at it," she said confidently in December 2023.

Continue scrolling to see Taylor’s career in photos:

Holland Taylor Through the Years

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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 successful career since she first appeared on TV as Denise Cavanaugh in The Edge of Night in 1977. She won her first Emmy Award in 1999 for her role in The Practice.

Taylor's career started with her role as Mrs. Arnold in J.T. and her first film appearance was in The Next Man in 1976. Some of her most well-known roles include Evelyn Harper in Two and a Half Men, Peggy Peabody on The L Word, Professor Elspeth Stromwell in Legally Blonde, Ellen Kincaid in Hollywood, and Cybil Richards in The Morning Show.

Taylor looked back on her extensive career during her appearance on the “LGBTQ&A” podcast in 2020.

Reflecting on her journey, Taylor shared, “I’ve been fortunate to have a unique career as an actor. Unlike many in this field, I have been able to consistently find work throughout the years. While the early days were challenging due to my age limiting the roles I could play, once I found my groove, I have been fortunate to avoid extended periods of struggle.”

The actress, who turned 80 in 2023, is busier than ever. In a conversation with Advocate, she shared how life can be successful for people in their 80s and even 90s.

She mentioned Ridley Scott, who at 86 is releasing a new movie about Napoleon, as well as Martin Scorsese in his late 80s and Clint Eastwood in his 90s, who are still actively directing. According to the actress, these examples show that individuals over 80 can not only continue working but also excel in their roles.

Continue scrolling to see Taylor’s career in photos:

Holland Taylor Through the Years

Credit: Cover Images

1965 to 1967

Taylor made her Broadway debut in 1965 in The Devils, followed by a role as Irene in Off-Broadway's The Poker Sessions in 1967. She continued to showcase her talent in productions such as Colette (1970), Butley (1972), We Interrupt This Program (1975), and Murder Among Friends (1975).

Holland Taylor Through the Years

Credit: Frank Edwards/Fotos International/Getty Images

1977 to 1980

Taylor's big break on television came when she played Denise Cavanaugh on The Edge of Night. She became well-known for her role in the 1980s sitcom Bosom Buddies, where she starred alongside Tom Hanks.

Holland Taylor Through the Years

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1984 to 1994

Taylor continued her acting career by appearing in Me and Mom (1985), Going Places (1990), and The Powers That Be (1992) where she starred alongside John Forsythe and David Hyde Pierce. In 1994, she took on the role of Dean Susan McMann in Saved by the Bell: The College Years just before the show was cancelled.

Holland Taylor Through the Years

Credit: Getty Images

1995 to 1998

Taylor played the role of newspaper editor Camilla Dane on the TV show The Naked Truth. She was one of the few actors who stayed on the show until it ended in 1998.

After her success on television, Taylor made her way into the film industry. She appeared in movies like How to Make an American Quilt (1995) alongside Winona Ryder, The Truman Show (1998) with Jim Carrey, and Next Stop Wonderland (1998).

Holland Taylor Through the Years

Credit: Frank Micelotta/ImageDirect

1999

Taylor won her first Emmy Award for her role as Judge Roberta Kittleson in The Practice, earning the title of Outstanding Supporting Actress in a Drama Series. Originally intended as a one-time appearance, Taylor's performance led her to become a regular cast member on the show from 1998 to 2003.

Holland Taylor Through the Years

Credit: Kevin Winter/ImageDirect

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.

Holland Taylor Through the Years

Credit: Michael Caulfield/Getty Images for PCA

2005 to 2010

During this time period, Taylor was known for her role as Evelyn Harper on Two and a Half Men, where she appeared alongside Charlie Sheen and Jon Cryer. Her performance earned her four Emmy Award nominations for Outstanding Supporting Actress in a Comedy Series.

Holland Taylor Through the Years

Credit: Michael Tullberg/Getty Images

2011 to 2013

During this period, Taylor dedicated her time to researching, writing, and producing a one-woman play centered on the life of the late Texas governor Ann Richards, titled Ann: An Affectionate Portrait of Ann Richards. The production made its debut in Chicago as a pre-Broadway engagement before moving to the Kennedy Center from December 2011 to January 2012. Following its success, the play was also staged on Broadway the following year. Taylor's outstanding performance in the play earned her a Tony Award nomination for Best Lead Actress in a Play.

Holland Taylor Through the Years

Credit: Taylor HIll/ Film Magic

2016

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

There is a significant age gap between us, which surprises many people, including myself. But as the saying goes, "If she dies, she dies," Taylor jokingly mentioned.

A month later, it was revealed that Taylor was referring to actress Sarah Paulson.

Holland Taylor Through the Years

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Taylor's Work from 2017 to 2019

During this period, Taylor was involved in various projects such as Kepler’s Dream (2016), Gloria Bell (2018), and Bombshell (2019). Additionally, she took on the role of Ida Silver in the television series Mr. Mercedes, which was based on Stephen King’s trilogy with the same title.

Holland Taylor Through the Years

Credit: Amy Sussman/Getty Images

2020

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

Holland Taylor Through the Years

Credit: ia Dipasupil/WireImage

2021 to 2023

During this period, Taylor reunited with Witherspoon and collaborated with Jennifer Aniston and Steve Carell in The Morning Show, where she portrayed the character Cybil Richards. The series was renewed for a fourth season in September 2023, shortly before the premiere of season 3. Additionally, in 2023, she made an appearance in Billions as Dr. Eleanor Meyer.

Editor's P/S:

Holland Taylor's career is a testament to her talent and dedication to her craft. Despite facing age restrictions early on, she persevered and has enjoyed a long and successful career. Her Emmy Award-winning performance in "The Practice" and her iconic role as Evelyn Harper in "Two and a Half Men" are just a few examples of her versatility and range as an actress.

Taylor's positive attitude and refusal to let age define her are inspiring. She continues to work consistently and is an advocate for older actors. Her example shows that it is possible to age gracefully and continue to thrive in one's career and personal life.