Peter Farrelly called the film's box-office failure the biggest disappointment of the Farrelly brothers' career, attributing the failure to its release during the 1996 Olympics. Farrelly said it was a crushing blow to their ego. However, he said that six to eight months later, when the film was released on home video, it became a big hit.
Peter Farrelly and Bobby Farrelly met with Michael Richards privately to discuss a role in the movie. However, the conversation didn't go particularly well, and there a disagreement arose between Richards and the Farrelly brothers. At one point, Richards excused himself to use the private bathroom in their office. After Richards didn't return from the bathroom after within half an hour, the brothers broke down the door to see if he was okay. That's when they discovered that Richards had climbed out the window and left.
As is the case with most of his films, Bill Murray ad-libbed virtually every line he spoke, including commercial. He would read over the script, get the general idea, and then discard it. The Farrelly brothers, on the DVD commentary, said that they're very glad he did, because it was funnier.
According to Peter Farrelly and Bobby Farrelly, they didn't initially take Lin Shaye (The Landlady) seriously, after having already cast her in a small role in Dumm und Dümmer (1994) at the suggestion of New Line Cinema studio executive and Robert Shaye, who also happens to be Lin's brother. However, when Lin came in to read for this movie, the Farrelly brothers mistook her for a homeless person looking for an ashtray. The brothers politely tried getting her out until they realizing it was Lin, in character for the reading. The Farrellys were blown away and didn't see anyone else for the role. Shaye subsequently appeared in more of their films thereafter.
John Popper: Lead singer and harmonica player for Blues Traveler, has a bit part as the announcer for the Reno bowling championship. Blues Traveler, in Amish garb, appears at the end of the movie playing one of their songs.
Roger Clemens: The Major League Baseball pitcher as Skidmark, a patron in the restaurant scene where Roy punches out Ishmael. As of 2023, Clemens ranks ninth on the all-time wins list for Major League Baseball pitchers with 354 career victories, third in strikeouts with 4672, but only 219th with a career ERA of 3.125.