Another great misstep in terms of movies and the classics is The Great Gatsby, which as been made into a film four times. Since the story comes from Nick's point of view, translating that into film is a daunting task, and the various film versions of Gatsby suggest that it is impossible. One of the most famous versions stars Robert Redford and Mia Farrow as the star-crossed Gatsby and Daisy. Although Farrow is convincingly ditsy, Redform seems much too self-assured and suave to be Gatsby. The most recent version aimed on A&E and starred Mira Sorvino as an unusually self-aware version of Daisy and Paul Rudd as an unusually snarky version of Nick. Despite the star power of the films, none of them satisfyingly capture Fitzgerald's tone, wit, or scathing indictment of the American Dream.
Of course, there are countless movie versions of Shakespeare's plays. One particularly awkward attempt that stands out is Kenneth Branaugh's Love's Labours Lost, which he made into a 1940s style musical featuring Alicia Silverston (of Clueless fame) and Matthew Lillard (of Scooby Doo the movie). As the characters flitter about on the sound-stage sets that are supposed to evoke memories of Astaire and Rogers films and perform numbers by Gershwin, Porter, and Berlin, it becomes obvious that most of the cast are out of their element. Alicia Silverstone gives it the old college try but clearly has no clue as to what she is saying, and the singing and dancing are, for the most part, amateurish to the point of being embarrassing. While watching non-singers (aka supposedly regular folk) sing can be charming (see Alan Alda's supremely understated and lovely take on "Looking at You" from Woody Allen's Everyone Says "I Love You" for a successful example), watching people attempt to sing, dance, and interpret Shakespeare while being shaky on all counts is more painful than entertaining.