[10] A mixture of parts in big-budget and small-scale film projects came next, including Disturbing Behavior (1998), Go, Teaching Mrs. Tingle (both 1999), Wonder Boys, The Gift (both 2000), Abandon, Phone Booth (both 2002), The Singing Detective, Pieces of April (both 2003), First Daughter (2004), Batman Begins, Thank You for Smoking (both 2005), Mad Money (2008), Don't Be Afraid of the Dark (2010), Jack and Jill (2011), Miss Meadows (2014), Woman in Gold, Touched with Fire (both 2015), Logan Lucky (2017), Dear Dictator (2018), Coda (2019), Brahms: The Boy II, and The Secret: Dare to Dream (both 2020).

[12] She is the youngest of five children born to Kathleen, a homemaker and philanthropist, and Martin Joseph Holmes Sr., an attorney who played basketball at Marquette University under coach Al McGuire.

[20] In January 1997, Holmes went to Los Angeles for pilot season, when producers and cast shoot new programs in the hopes of securing a spot on a network schedule.

[20] Columbia TriStar Television, producer of a new show named Dawson's Creek that was created by screenwriter Kevin Williamson, asked her to come to Los Angeles to audition, but there was a conflict with her schedule.

"[24] Creator and executive producer Kevin Williamson said Holmes has a "unique combination of talent, beauty and skill that makes Hollywood come calling.

Jancee Dunn, an editor at Rolling Stone said she was chosen for the cover because "every time you mention Dawson's Creek you tend to get a lot of dolphin-like shrieks from teenage girls.

"[30] During her time as a series regular on Dawson's Creek, Holmes's first leading role in a film came in 1998's Disturbing Behavior, a Scream-era Stepford Wives-goes-to-high school thriller, where she was a loner from the wrong side of the tracks.

Roger Ebert, then of the Chicago Sun-Times wrote of her character, Rachel, "dresses in black and likes to strike poses on the beds of pickup trucks and is a bad girl who is in great danger of becoming a very good one.

The same year, in Kevin Williamson's Teaching Mrs. Tingle, which he wrote and directed, Holmes played a straight-A student whose vindictive teacher (Helen Mirren) threatens to keep her from a desperately needed scholarship.

Holmes had a small role (six and a half minutes of screen time) as Hannah Green, the talented student who lusts after Professor Grady Tripp (Douglas's character, who is her instructor and landlord).

"[26][36][37] Her second feature film during 2000 was The Gift, a Southern Gothic story directed by Sam Raimi and starring Cate Blanchett, she played the antithesis of Joey Potter: a promiscuous rich girl having affairs with everyone from a sociopathic wife-beater (Keanu Reeves) to the district attorney (Gary Cole), and is murdered by her fiancé (Greg Kinnear).

[39] 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. Peepers character and singing "Big Spender" from Sweet Charity.

In the 2002 film Abandon, written by Oscar winner Stephen Gaghan, Holmes plays a delusional, homicidal college student named "Katie".

"[43] "Each actor shines", wrote Elvis Mitchell, "even Ms. Holmes, whose beauty seems to have fogged the minds of her previous directors" in playing "a brat who is slaving to find her inner decency and barely has the equipment for such an achievement, let alone to serve a meal whose salmonella potential could claim an entire borough.

Kirk Honeycutt called her character Samantha Mackenzie "a startling example of how a studio film can dumb down and neutralize the comic abilities of a lively young star.

"[50] She also appeared in the film version of Christopher Buckley's satirical novel Thank You for Smoking, about a tobacco lobbyist played by Aaron Eckhart, whom Holmes's character, a Washington reporter, seduces.

[citation needed] After speculation about Holmes reprising her role in The Dark Knight, the sequel to Batman Begins, it was finally confirmed that she would not appear.

Ben Brantley of The New York Times claimed "the neophyte Ms. Holmes" is a "sad casualty" of director Simon McBurney's "high concept approach" to the play.

"[64] In 2009, Holmes appeared in the National Memorial Day Concert on the Mall in Washington, D.C. in a dialogue with Dianne Wiest celebrating the life of an American veteran seriously wounded in Iraq, José Pequeño.

[68] Holmes and Chace Crawford were reportedly cast as the leads in the romantic comedy Responsible Adults, to begin shooting in Los Angeles in "Fall 2011".

[72] In 2015, Holmes directed a short documentary for ESPN about Olympic gymnast Nadia Comăneci titled, Eternal Princess, that premiered at the Tribeca Film Festival.

[75][76] The film stars Holmes, Stefania LaVie Owen, Luke Wilson, Richard Kind, Mark Consuelos, Judy Greer and Eve Lindley.

[77] The New York Times wrote: "The soul of the movie is the complicated mother-daughter relationship, which changes as Ruthie, who narrates the story, observes Rita making the same mistakes again and again.

[79] The same year, she made a cameo in the movie Ocean's 8, starring Sandra Bullock, Cate Blanchett, Anne Hathaway, Mindy Kaling, Sarah Paulson, Rihanna, Helena Bonham Carter, and Awkwafina.

[85] The same year, she was the main character in the movie The Secret: Dare to Dream co-starring Josh Lucas, Jerry O'Connell and Celia Weston, which was released in the United States through video on demand, and theatrically in several countries, on July 31, 2020, by Roadside Attractions and Gravitas Ventures, following the COVID-19 pandemic.

[92] The film stars Katie Holmes, Jim Sturgess, Derek Luke, Melissa Leo, Zosia Mamet, and Becky Ann Baker.

[97][98] In 2024, Holmes starred in the Broadway revival of Our Town by Thornton Wilder, portraying Mrs. Webb opposite Richard Thomas, Jim Parsons and Zoey Deutch.

[106] In July 2009, Holmes, Nigel Lythgoe, Adam Shankman, and Carrie Ann Inaba announced the launch of a dance scholarship fund called the Dizzy Feet Foundation.

[126] The suit was settled on April 27, 2011, after which Star wrote a public apology in the May 6, 2011, issue of their magazine, and made an "undisclosed substantial donation" to Holmes's charity, Dizzy Feet Foundation.

[128][129] Following the announcement, those close to Holmes stated that she believed she had reason to fear that Cruise would abduct Suri and was also apprehensive of intimidation by the Church of Scientology.