Leatherheads

While filming near Travellers Rest in South Carolina, George Clooney stopped at a children's lemonade stand and paid the children running it one hundred dollars each for a glass of lemonade.

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John Krasinski had to change his usual hairstyle for this role. The hair change was written into a storyline on the television series The Office (2005).

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Actor and director George Clooney claimed he rewrote every scene except two and asked the WGA for credit. When his request was denied, he gave up his status as a voting member and changed it to "Financial Core Member."

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Carter Rutherford was largely based on real-life football star Harold "Red" Grange. His agent in the film, C. C. Frazier, was based on his real-life agent, C. C. Pyle.

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The character Dodge Connelly was largely based on 1920s football star Johnny "Blood" McNally, who was known for his great football talent but even more for his off-the-field antics.

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The screenplay was written in 1993. The writers brought the project to Steven Soderbergh's attention, and he took it to Casey Silver, then head of production at Universal Pictures. After Silver left the studio to become an independent producer, the script fell into limbo. Soderbergh later returned and brought George Clooney with him to make the film.

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The motorcycle George Clooney rides is not an antique but a custom-built, electrically powered replica of a 1918 Indian motorcycle.

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More than four hundred local extras were hired. They were paid about nine dollars an hour.

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While preparing for this film, George Clooney watched many old screwball comedies.

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The Duluth Bulldogs are largely based on the real NFL team the Duluth Kelleys/Eskimos, which existed from 1923 to 1927. Because Duluth was then the northernmost team in the NFL, the harsh Minnesota winters meant the team rarely played at home in November and December. That made them mostly a traveling team and caused them to play fewer games than the rest of the league. Their best season came in 1924, when they finished with a 5-1 record, placing them 4th by winning percentage. In 1926 they completed their first and only season with a 6-5-3 record, finishing 8th in the standings. Also in 1926 they played their last home games in Duluth, and in 1927 they played every game on the road, finishing with a 1-8 record. After the season the team's rights were sold back to the NFL by the team's owner, and the Duluth Eskimos no longer existed. The team's owner was supposed to hold the rights to any future NFL Minnesota football team, but in 1961 he was granted ownership of only 10% of the Minnesota Vikings, with the other 90% held by outside investors.

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The building Dodge Connelly (George Clooney) arrives at on his motorcycle just before meeting Lexie Littleton (Renée Zellweger) for the first time is the Poinsett Hotel in downtown Greenville, South Carolina. The Poinsett Hotel was built in 1924 but did not open until June 1925.

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This was originally going to be a Mel Gibson film.

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Throughout the film, until the bar fight scene, it is not clear to the audience whether Dodge fought in World War I or merely claimed to have fought. In a deleted scene, Dodge tells Carter and Lexie that he did fight in the war but was wounded and sent home. Later, when Dodge fights Carter, he tells Carter to avoid hitting parts of his right leg. Based on this and the deleted scene, it can be inferred that Dodge's war injury was to his right leg.

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Actor and director George Clooney and Renée Zellweger premiered the film on March 24, 2008, in Clooney's hometown of Maysville, Kentucky. In 1953 his aunt Rosemary Clooney had premiered her own film The Stars Are Singing (1953) in the same town, though not in the same theater. About 3,000 fans attended the red carpet event, while two hundred VIPs were selected to watch the film. An additional screening was then held, and one hundred lucky winners each won two tickets in a raffle. Clooney and Zellweger also hosted the second screening before leaving the theater. Among the guests were former Kentucky Lieutenant Governor Steve Henry and his wife, Miss America 2000, Heather Renee French-Henry.

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The cast includes three Oscar winners: George Clooney, Renée Zellweger and Grant Heslov, and one Oscar nominee: Jonathan Pryce.

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Randy Newman (who composed this film) and Malcolm Goodwin (who plays Bakes) share the same birthday (November 28), but were born thirty-nine years apart. Newman was born in 1943 and Goodwin in 1982.

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