In an interview on the Late Show with David Letterman, Clooney mentioned the plot is loosely based on George Halas's signing of University of Illinois football star Harold "Red" Grange. Grange was signed to a contract with the Chicago Bears in 1925, the day after his final game at Illinois.
The team itself is loosely based on the Duluth Eskimos. Clooney later explained that "We wanted to call them the Eskimos, but because we were drinking in the movie, the NFL said we couldn't use the actual names." The Canton Bulldogs was the first successful pro football team, which is why the Professional Football Hall of Fame is located in Canton, Ohio.
Leatherheads began filming on February 12, 2007. Filming locations mainly included locations in Chattanooga, Tennessee, upstate South Carolina around Anderson, Greenville, Ware Shoals, Greer and Travelers Rest, as well as Boiling Springs and western North Carolina around Statesville, Greensboro and Winston-Salem, specifically at Hanes Middle School and the Winston-Salem Millennium Center. Additional train scenes were filmed in the Winston-Salem suburb of Tobaccoville, specifically in the community of Donnaha.
The crew and cast headquarters during the Winston-Salem scenes were based in the nearby town of East Bend, in Yadkin County, NC. The football game scenes at the beginning and at the end of the picture were filmed at Memorial Stadium, near Central Piedmont Community College in Charlotte, North Carolina, with technical advisor T.J. Troup "teaching them the intricacies of 1920s football so that they look and sound like real players of the era."
Train scenes were filmed at the North Carolina Transportation Museum in Spencer, North Carolina and The Tennessee Valley Railroad Museum in Chattanooga, TN. Filming wrapped in mid-May 2007. After initially being set for release in December 2007, the studio moved the release date to April 4, 2008.
On March 24, George Clooney and Renée Zellweger premiered the film in Maysville, Kentucky, birthplace of Clooney's father and aunt, Nick Clooney and Rosemary Clooney. Clooney and Zellweger visited Duluth to promote the film.
The piano player bent over the tack piano with eyes glued to music is the composer of the original music in this film, Oscar-winning songwriter Randy Newman.
The George and Ira Gershwin song "The Man I Love" is sung in the film but the song was not extant in 1925. It was "part of the 1927 score for the Gershwin antiwar musical satire Strike Up the Band".
The motorcycle that Clooney and Zellweger rode in Leatherheads is not a vintage V-twin motorcycle. It is one of three custom-built 36-volt electric-powered Indian replicas.
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