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The story that Billy Crystal tells about his "best day" of going to a Yankee game with his father is a true story from his childhood. He notes at one point that, "I still have the program." Not only does he really still have it, but he got Mickey Mantle to autograph it twice: once at the game that day and once again some 20 years later on a talk show they were both guests on.
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Billy Crystal co-wrote the story, but is not given on-screen credit.
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Some trailers feature a scene where someone's spurs are caught on a rail, but this scene is not in the movie.
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The cow-giving-birth used a puppet calf, as several takes were wanted. The shot of Norman getting to his feet was real footage taken just after birth. Billy Crystal actually assisted in the delivery. Six calves were used in all, and Crystal arranged for them all to live full lives on a farm. The shots featuring Crystal were filmed in Colorado, but the shots from the same scene featuring Jack Palance were filmed in New York.
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Billy Crystal liked the horse he rode so much, he bought him.
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The horse that Billy Crystal rides in the movie is named Beach Nut and is the same one he rides in City Slickers II: The Legend of Curly's Gold.
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Bruno Kirby was extremely allergic to horses. Prior to each day of filming involving a horse, he required an injection of allergy medication to get through the day's shooting.
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Daniel Stern declined the riding lessons offered for the movie in order to better convey his character's inexperience at horse riding.
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There is a 38-year gap between Jack Palance's Oscar nomination for Shane in 1953 and his win for City Slickers in 1991.
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Billy Crystal's father ran a jazz label in New York and thus introduced him to many legends of the Jazz world, including Billie Holiday who took a seven year old Billy to his first movie. The movie was Shane featuring Jack Palance.
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Rick Moranis was cast in a major role but left the project because of creative differences.
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Jake Gyllenhaal's film debut.
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Aside from the Yankee game story that Mitch tell, another true story from Billy Crystal's life is the wake up call from his mother on his birthday. According to Billy in the DVD Commentary, in real life, his mother would call him on his birthday at around 5 o'clock in the morning (the time he was born) and verbally re-enact the event over the phone. The rendition in the film is word-for-word the true story of Billy Crystal's birth.
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Billy Crystal, a notoriously die hard New York Yankees fan, wears a New York Mets cap in the film. As explained by Crystal in the DVD Commentary, he did this because the New York Mets had made a major contribution and helped out on his annual Comic Relief charity.
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According to Billy Crystal in the "making of" documentary, when he first came up with the story and came up with the character of Curly, he immediately wrote down Jack Palance's name as the ideal choice for the role. No other actor was considered for the role.
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The scene where Mitch, Ed, and Phil cross the river with the herd and save Norman from the rapids were amongst the first scenes filmed.
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The last scene Jack Palance filmed was the moment where he and Billy Crystal are sitting at the campfire and singing trail songs.
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True to form and fashion of Billy Crystal, he performs a Vaudevillian act for Jack Palance, at the 1992 Academy Awards. Both actors receive ovations for this, along with their awards.
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Although many observers were stunned by Jack Palance's "I crap bigger than Billy Crystal!" comments at the 1991 Oscars, and didn't understand where his statement came from, Palance was actually repeating a line that his Curly character says to Crystal when they first meet at the riding camp. People forgot this line because Palance delivered it so quickly and had many more notable quotes.
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