At the first read-through of the script, Judge was pleased with Herman's performance, and felt Stephen Root improved on his own take on Milton, but was not happy with the rest of the cast. He considered abandoning the film, but Rothman said it worked and just needed the right actors. According to Judge, while Fox at first told him to just get the best actors possible since the film's budget would not be large enough to consider bankable stars, the studio soon changed its mind. In the wake of the success of "Good Will Hunting", he was advised to get that film's stars, Ben Affleck and Matt Damon. Again, he almost changed his mind about the film (Rothman said in 2019 that while A-list stars are often unlikely to take roles in low-budget productions, those films should nevertheless make the effort to attract them). He had agreed to meet with Damon in New York, but then Ron Livingston's agent asked if his client could audition for the lead. Casting director Nancy Klopper was impressed, and after Judge saw the video he told the studio that he wanted Livingston in the part.