Shakespeare in Love (1998)
What is it? A witty rom-com centred around a young, sexy Shakespeare (Joseph Fiennes) and his love affair with an heiress in disguise (Gwyneth Paltrow) as he attempts to write Romeo and Juliet. John Madden directs, with a brilliant script by Marc Norman and Tom Stoppard.
Why did it win? Because it's an effortless watch with a quality ensemble cast (never hurts) and a glamorous leading lady. Also, the Academy doesn't really seem to like giving Spielberg Oscars unless given no option, Life is Beautiful was too foreign, The Thin Red Line too arty and Elizabeth just a little too dry.
Did it deserve to win? Well, it's hard to argue that this is better than either Spielberg or Malick's World War II, but it's certainly more likeable, which never hurts when trying to appeal to Academy voters: very few total downers actually win the big prize. Tragedy is fine, but it should ideally be of the bittersweet or pyrrhic victory variety.
Worth a look? Absolutely. The dialogue's cracking and the cast even starrier than you remember.