1990–2008: Established actor
In 1990, Daniels starred in the thriller Arachnophobia. He also starred in a pair of romantic comedies, Love Hurts (1990) and The Butcher's Wife (1991), playing Demi Moore's love interest in the latter. His sci-fi vehicle Timescape (1992) went straight to video. His next significant role was as Colonel Joshua Chamberlain in Gettysburg (1993). Daniels reprised the role of Chamberlain 10 years later in the prequel film Gods and Generals.
Daniels continued his work in the theater with Redwood Curtain (1993). Off-Broadway, he starred in Lanford Wilson's Lemon Sky with Cynthia Nixon where he received a Drama Desk nomination for and an Obie Award for his performance in the Circle Repertory Company production of Johnny Got His Gun.
In 1994, Daniels co-starred with Jim Carrey in one of his most commercially successful films, Dumb and Dumber. It was a noted departure for Daniels, owing to his status as a dramatic actor. Earlier that year, Daniels appeared with Keanu Reeves in the action blockbuster Speed; the film was an enormous hit, grossing over $350 million at the box office. Daniels would then host Saturday Night Live a second time before the release of the 1996 Disney live-action remake of 101 Dalmatians. Daniels starred as the owner of a litter of dalmatians stolen by the evil Cruella De Vil (Glenn Close). The film was successful, grossing $320 million. Daniels plays a grungy cop Alvin Strayer along with Eric Stoltz in 2 Days in the Valley. Also in 1996 was the family hit film Fly Away Home with Daniels as the supportive single father of Anna Paquin's goose-raising preteen. Daniels then had a critical and commercial misfire with Trial and Error (1997). He would rebound, however, with 1998's Pleasantville as diner owner Bill Johnson, who learns to act as an individual and rebel against the norm at the urging of Tobey Maguire's David. Also starring Reese Witherspoon, Joan Allen, and Don Knotts, Pleasantville was nominated for three Academy Awards. Daniels starred alongside Christopher Lloyd's comedy My Favorite Martian.
Daniels starred in the TV films The Crossing, Cheaters, and the direct-to-video release Chasing Sleep. At this point, in the early 2000s, he began to focus more on his theater work at The Purple Rose Theatre as well as writing, starring, and directing the films Escanaba in da Moonlight and Super Sucker. Daniels's next major film role would be in Clint Eastwood's Blood Work, which received mixed reviews and was a commercial failure. He would rebound later that year with Stephen Daldry's Academy Award-winning The Hours alongside Meryl Streep, Julianne Moore, and Nicole Kidman. The film was also a financial success, grossing well over $100 million. Gods and Generals followed in 2003, as did the action film I Witness, which co-starred James Spader. Daniels then starred in Imaginary Heroes and the 2004 television film adaptation of fellow Michigander and friend Mitch Albom's bestseller The Five People You Meet in Heaven.
The year 2005 proved to be a strong year for Daniels as he garnered notice as the star of the lauded Noah Baumbach film The Squid and the Whale with Laura Linney. Daniels received his third Golden Globe nomination for the film, about a divorcing couple and the effect the split has on their children. That year Daniels also starred in the family film adaptation of Because of Winn-Dixie. He would round out the year with a supporting role in George Clooney's Oscar-nominated film Good Night and Good Luck, starring David Straithairn, Patricia Clarkson, Robert Downey Jr., and Frank Langella. In 2006, Daniels appeared in the Truman Capote biopic Infamous starring Toby Jones, Sandra Bullock, Gwyneth Paltrow, and Sigourney Weaver. The film was compared by critics to Bennett Miller's 2005 film Capote starring Philip Seymour Hoffman, Catherine Keener, and Chris Cooper.
Daniels then starred in Barry Sonnenfeld's family film RV (2006), alongside Robin Williams, as the redneck comic foil to Williams' uptight businessman. Daniels appeared in an Off-Broadway production of David Harrower's Blackbird in 2007 alongside Allison Pill, with whom he would later reunite in Aaron Sorkin's The Newsroom. He also starred in two 2007 independent films, Mama's Boy and The Lookout, for which he was nominated for a Satellite Award, and Traitor (2008) with Don Cheadle.