1.'Gone with the Wind'
Directed by three different directors (Victor Fleming, George Cukor, and Sam Wood) and released in 1939, with one of the most complex heroines in film, "Gone with the Wind" is the story of Scarlett O'Hara, a Southern belle who suddenly has to face the Civil War and Reconstruction which bring an end to her world, and Rhett Butler, the sardonic blockade runner who falls in love with her. Actress Hattie McDaniel, who played grumbling house servant Mammy in the film and won an Academy Award for it (the first African-American actor to win one), did not attend the première of the film after MGM strongly suggested she not go because of the segregationist laws in Atlanta where the première took place. Clark Gable was furious and said he wouldn't attend if McDaniel was not allowed to, but McDaniel persuaded him to go.
'The Philadelphia Story'
Try to figure out who ends up together at the end of the 1940 film directed by George Cukor – the movie's final minutes keep you guessing. Rich Philadelphia socialite Tracy Lord (Katharine Hepburn) is about to marry a businessman, but a reporter (James Stewart) and a photographer (Ruth Hussey) are determined to get a scoop on the wedding – and Tracy's ex-husband (Cary Grant) has shown up for the fun. The movie's original tagline was the cringe-worthy "The snooty society beauty who slipped and fell – IN LOVE!" During the shooting of the film, Stewart improvised his hiccuping in a scene where the reporter he plays is drunk while talking with ex-husband C.K. Dexter Haven. You can see Grant desperately trying not to laugh.
The 1942 movie directed by Michael Curtiz tells the story of Rick (Humphrey Bogart), a cynical nightclub owner living in Casablanca, whose ex-girlfriend Ilsa (Ingrid Bergman) walks into the club one night looking for papers to escape to America – with her resistance-leader husband. Ilsa is still in love with Rick, but, according to Rick, three people's happiness may not "amount to a hill of beans in this crazy world," referring to World War II. Interestingly, the oft-quoted line "Play it again, Sam," referring to pianoman Sam playing Rick and Ilsa's song "As Time Goes By," is never actually said in the film. Ilsa says, "Play it, Sam," and Rick says later, "You played it for her, you can play it for me! Play it!"
'West Side Story'
The 1961 film directed by Jerome Robbins and Robert Wise is based on the hit musical, which was based on "Romeo and Juliet" – so get your tissues ready. American-born gang members, the Jets, are battling for New York City territory with the Puerto Rican gang members, the Sharks, and nothing seems to be able to stop the feud. But when one of the leaders of the Jets, Tony, sets eyes on Maria, the sister of the leader of the Sharks, it's love at first sight. During filming, the actors who played the Jets were kept apart as much as possible from those who played the Sharks, and the actors playing the gang members were encouraged to play practical jokes on their rivals.
The 1977 film directed by star Woody Allen is the story of Alvy Singer (Allen) who meets Annie Hall (Diane Keaton), the flighty woman famously dressed in menswear. With only-in-a-Woody-Allen-movie flashbacks, the storyline dips into the two characters' pasts and includes long monologues from Allen on the nature of life and love. Keaton's last name is actually Hall and she has sometimes been called Annie as a nickname, prompting many to believe that the movie was based on the real-life relationship between Allen and Keaton. Allen says this is not true.
In director Norman Jewison's 1987 film, Loretta (Cher), who lost her husband years earlier in an accident, is now accepting the proposal of nice guy Johnny (Danny Aiello), despite not being in love with him. She thinks marrying him will put her life in order, until she meets Johnny's brother Ronny (Nicolas Cage) and falls in love. MGM, the movie's studio, didn't want to hire Cage after his screen test, but Cher was convinced he was the right one for the part and threatened to quit unless he was hired.
'The Princess Bride'
The 1987 quirky fairy tale directed by Rob Reiner follows Wesley (Cary Elwes), a farm boy who falls in love with Buttercup (Robin Wright), the daughter of the family for whom he works. Wesley goes to sea to try to earn money so they can be together, but soon a multitude of obstacles stand in their way, including a sinister prince, a man with six fingers, a sword-fighting Spaniard, and a Machiavellian plotter who likes to shout, "Inconceivable!" The writer of the original book, William Goldman, visited the set one day when a scene was being filmed in which Wright's dress became engulfed in flames when she was in a fire swamp. Goldman got so caught up in the scene that he yelled, "Her dress is on fire!" and they had to shoot the scene again.
'When Harry Met Sally...'
The 1989 film also directed by Rob Reiner asks the famous question if men and women can ever truly be only friends. Harry Burns (Billy Crystal) first meets Sally Albright (Meg Ryan) when they drive to New York together from Chicago after college is over, and during the trip, they argue about whether men and women can have a platonic relationship. The question comes up again years later when they run into each other and become close friends. Throughout the film, married couples tell the story of how they met in documentary-style scenes, and while the couples are played by actors, the stories they tell are all real stories collected by the production team.
The 1997 film by James Cameron about the tragic sinking of the massive ocean liner is also the story of a rich passenger, Rose DeWitt Bukater (Kate Winslet), and working-class Jack Dawson (Leonardo DiCaprio), who meet despite the stringent class separation on the ship. Winslet and DiCaprio ad-libbed the scene early on in the film in which Rose thanks Jack for saving her life, and the scene in which Jack teaches her to spit was almost entirely improvised as well. The water in which Winslet and DiCaprio both spend much of the second half of the movie was from the Pacific Ocean and was incredibly cold – DiCaprio shouted "This is cold!" and Winslet gasped as they got in, both unscripted. Cameron left the reactions in the movie.
The 2005 film directed by Ang Lee tells the story of two cowboys, Ennis (Heath Ledger) and Jack (Jake Gyllenhaal), who meet herding sheep in Wyoming in 1963 and fall in love. Multiple actors turned down the two starring roles, and when Ledger read the script based on the short story by Annie Proulx, he said he considered it the best script he'd ever read. The film was widely considered to be a frontrunner for Best Picture, but famously lost out to the movie "Crash" for the 2005 Best Picture Oscar.