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Her appearance was lamented by Variety's Steven Kotler.
Holmes hosted Saturday Night Live on February 24, 2001, participating in a send-up of Dawson's Creek where she falls madly in love with Chris Kattan's Mr.
She has also played on Broadway in a production of Arthur Miller's All My Sons, and had numerous guest roles on television programs such as How I Met Your Mother.
In 2011, she starred as Jacqueline Kennedy in The Kennedys miniseries, a role she reprised in the 2017 miniseries The Kennedys: After Camelot.
The first was in Wonder Boys, directed by Curtis Hanson from the novel by Michael Chabon.
The film told the story of a creative writing teacher at a university, with Michael Douglas in the leading role.
"It was very difficult for me to leave Wilmington, to have my little glass bubble burst and move on. On the other hand it was refreshing to play someone else", she said in 2004.
Holmes' first starring role post-Dawson's Creek was in 2003's Pieces of April, a gritty comedy about a dysfunctional family on Thanksgiving.
Many critics and audiences agreed that Holmes had given her best performance in the film as April.
Yet it is her surliness, as well as her intransigent determination to make Thanksgiving work, that keeps the laughs coming." Holmes also received a Satellite Award for Best Actress for the role.
On the November 9, 2003 episode, she was Punk'd by Ashton Kutcher and the next year she was the subject of an episode of the MTV program Diary. She later played the President's daughter in First Daughter, which was originally to be released in January 2004 on the same day as Chasing Liberty, another film about a president's daughter, but was ultimately released in September 2004 to dismal reviews and ticket sales.