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.
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.
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 script was written back in 1993. The writers brought it to the attention of Steven Soderbergh who then took it to the then-President of production at Universal Pictures, Casey Silver. It went into script limbo after Silver left the studio to become an independent producer. Soderbergh then came back and brought George Clooney along to make this movie.
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.