The studio wanted someone from the cast of That '70s Show (1998) for the role of Carter and had originally given it to Ashton Kutcher. Kutcher dropped out due to creative differences, and Topher Grace auditioned and got the part. Grace had auditioned four times for the role, and had to convince producer Paul Weitz that he was right for the role, by highlighting his raising by his father, a businessman with sharp negotiation skills.
When Alex (Scarlett Johansson) is moving in to the NYU dorm, she and Dan (Dennis Quaid) walk past a poster in the dorm hallway. Showing an enormous marijuana leaf, the full text of the poster reads "Marijuana. Because Your Friends Just Aren't Very Funny."
The Sports America issue that Dan shows to Eugene Kalb during his sales pitch early in the movie has a cover featuring Carmelo Anthony of the Denver Nuggets. The other magazines shown during the movie are on screen too briefly or from too far away to positively identify the cover subject.