In 1997, Eckhart was approached by Neil LaBute to star in a film adaptation of LaBute's stage play In the Company of Men. Eckhart played a frustrated white-collar worker who planned to woo a deaf office worker, gain her affections, then suddenly dump her. Eckhart's performance was well-received by critics. Paul Tatara of CNN.com wrote, "Eckhart's Chad even has a couple of sarcastic diatribes that mock Cristine's halting, hollow-voiced way of speaking." In the Company of Men was a critical success, winning Best First Film at the 63rd annual New York Film Critics Circle Award. Eckhart's performance won him the Independent Spirit Award in the category of Best Debut Performance. The film was ranked as one of "The 25 Most Dangerous Movies" by Premiere magazine.
The following year, Eckhart starred in another LaBute film, Your Friends & Neighbors (1998), as Barry, a sexually frustrated husband in a dysfunctional marri