For this role, John Krasinski had to change his usual hairstyle. This hair change was worked into a story on his television show, The Office (2005).
The Dodge Connelly character was loosely based on 1920s football star Johnny "Blood" McNally, who was known for his great football skills, but even more for his off-the-field incidents.
While filming on-location near Travelers Rest, South Carolina, George Clooney dropped by a kids lemonade stand and paid the kids running the stand one hundred dollars apiece for his glass of lemonade.
Actor and director George Clooney claimed that he had re-written all but two scenes, and had asked the WGA for credit. When they denied his request, he removed himself as a voting member and changed his status to "Financial Core Member".
Carter Rutherford was loosely based on real-life football star Harold "Red" Grange. His agent in this movie, C.C. Frazier, was based on his real-life agent, C.C. Pyle.