Hugh Jackman took etiquette lessons from 19th-century etiquette expert Jane Gibson (who trained actors for such projects as Sense and Sensibility (1995)). He also studied ballroom dancing and trained to ride a horse for the film.
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According to the DVD commentary, several of the film's actual crew members appear in the crew of the margarine commercial.
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When Meg Ryan knew that Hugh Jackman was going to spend his wedding anniversary alone, she phoned his wife to invite her to dinner. Reportedly, Jackman had to spend the day working.
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When Leopold is chasing Stuart down the stairs and out of his house, Stuart seems to jump a few meters in a second. In the "Director's Cut" version, the two guys actually bump into Kate there.
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Hugh Jackman and Liev Schreiber would later co-star as half brothers and mortal enemies Wolverine and Sabretooth in X-Men Origins: Wolverine (2009). James Mangold would also go on to direct the sequels, The Wolverine (2013) and Logan (2017).
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There are 2 different versions of this movie available on the DVD menu. One is the theatrical version which runs for 113 minutes where the other one is a directors cut which is 7 minutes longer than the original version. The only differences between the two is Kate can be seen in 1876 at the very beginning as well as a surprise cameo by James Mangold at a movie conference. There is also the implication that Kate is a distant relation to Stuart.
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Albany, New York was named after the then Duke of Albany in 1664.
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The violin piece being performed during Kate and Leopold's rooftop dinner is Jascha Heifetz's transcription of Leopold Godowsky's "Alt-Wien", or "Old Vienna". Godowsky subtitled his work, originally written for solo piano, "Whose yesterdays look backward with a smile through tears".
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Sandra Bullock was originally in contention for the part of Kate.
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Viola Davis has a minor part as police officer who gives Hugh Jackman a ticket. Twelve years later, they would co-star and play family friends in the film Prisoners (2013).
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When Leopold wakes up in Stuart's apartment for the first time, he accidentally turns on the television, and an episode of The Prisoner (1967) is on.
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This marks Hugh Jackman's second romantic comedy; Someone Like You (2001) was his first. This also marks Jackman's fourth Hollywood movie.
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In this movie, Meg Ryan pays a character named Kate. She played Kate in French Kiss (1995). In You've Got Mail (1998), she played Kathleen, whose nickname is Kate. In Restoration (1995), she was Katharine - another Kate.
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In the beginning of the movie, Leopold looks back at Stuart during the bridge dedication speech. Behind Leopold's head, a spectator in the crowd waves a 37-star U.S. flag which is the correct number of stars from 1867 to 1877 (8 stars on top, 3 rows of 7 stars, 8 stars on bottom).
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Also on the wall of Stuart's apartment is a Spanish-language poster for the movie "Cerebro Atomico" ("The Atomic Brain"), starring Gene Nelson. Although this 1955 film is known to American audiences as The Atomic Man (1955), the movie's original title was "Timeslip," which is appropriate for this film. (The other, more visible Spanish-language movie poster in Stuart's apartment is "Yo Nombrare Al Asesino" (I'll Name the Murderer (1936).)
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Both this and The Greatest Showman (2017) featured the unfinished Brooklyn Bridge.
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Viola Davis makes an early career appearance as a police officer.
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In Stuart's apartment, there is a framed poster of the 1969 World Champion New York Mets.
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In the film's original edit, Stuart was Leopold's descendant, which was Stuart's reason for specifically tracking him down. Criticism that this plot line also meant that Kate was Stuart's ancestor led to those scenes being cut. In the Director's Cut, however, this plot line is followed.
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In an early version of the screenplay, Leopold is accidentally transported through time in an actual time machine developed by a group of scientists that includes Kate. They have a child (of whom Leopold is unaware) and eventually reunite during the Roaring '20s.
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The grey dress Kate wears at the end of the film looks like a modern two piece with a narrow profile in the present day scenes. When she slips through time, the dress has a small lace trim on the top of the corset and a sizable bustle on the back. While her dress effectively changes by going back through time, her modern side part hairstyle remains the same.
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The movie foreshadows Kate visiting Leopold's home three times. The first time is when Leopold and Kate are taking a walk in New York, and Leo spots his home; the next is when Kate attends her speech for her Vice President role; and the last one is when Kate goes back to 1876 to be with Leopold.
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Enchanted (2007) borrows elements from this film. Giselle is like Leopold as she's from a different time frame. Robert is like Kate where he starts off as a cynic and later tones down. Both characters don't get on initially, but then they do. The only differences are that this movie is not a musical, and Kate goes back to Leopold's time frame.
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