George Clooney watched many old Screwball-comedies in preparation for this movie.
For this role, John Krasinski had to change his usual hair style. This hair change was worked into a story on his television show, "The Office" (2005).
More than 400 local extras were hired. They were paid around $9 per hour.
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 Clooney along to make the film.
Star-director Clooney and his co-star Zellweger premiered this film in Clooney's hometown of Maysville, KY on March 24th, 2008. In 1953, his aunt Rosemary Clooney had premiered a film of her own, The Stars Are Singing (1953), in the same town, though not at the same theatre. Roughly 3,000 fans attended the red carpet event while 200 VIPs were hand-selected to watch the film. An additional screening was held afterward with 100 lucky winners winning 2 tickets apiece from a raffle drawing. Clooney and Zellweger hosted the second screening as well before departing the theatre. Among the guests in attendance were former Lt. Governor of Kentucky Steve Henry and his wife, Miss America 2000, Heather French Henry.
Clooney claimed that he had rewritten 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 is loosely based on the real life football star Red Grange. His agent in the movie, C.C. Frazier, is based on his real life agent C.C. Pyle.
The Dodge Connally character was loosely based off of 1920's football star Johnny "Blood" McNally, who was known for his great football skills, but even more for his off the field incidents.