Originally released in 1998, Shakespeare in Love took home seven Academy Awards including ones for picture, actress, and supporting actress. Beyond that, it was nominated for another six Oscars which it didn't win. Certainly the movie is entirely enjoyable and thoroughly entertaining, but watching it today, the John Madden directed film doesn't have the feeling of a "great" motion picture. Great fun, yes; great, no.
Shakespeare in Love stars Joseph Fiennes as William Shakespeare, a lovesick playwright looking for his muse, and Gwyneth Paltrow as Viola De Lesseps, a woman in love with the theatre, but not with the man to whom she is being forced to marry (Lord Wessex, played by Colin Firth). It is a period romantic comedy which, as much as being interested in telling a love story, seeks to gain too much mileage from jokes centering on winking to the audience about Shakespeare's plays and characters (an early idea for Romeo and Juliet has the play called Romeo and Ethel the Pirate's Daughter, Queen Elizabeth asks for a comedic play for Twelfth Night, the list goes on as do the quotes from Shakespeare's works).
This over-reliance on such jokes is a shame as the performances by the entire cast are truly top notch and between them and the love story there is more than enough here to make the picture an excellent one. The main love story between Viola and Will (as he is known in the movie) plays out wonderfully, and serves as the inspiration for Shakespeare to write Romeo and Juliet, the play on which he is currently working. The entirety of this story, while perhaps not historically accurate, plays out in terribly witty if not completely believable fashion and manages to maintain a great deal of levity despite the fact that it is clear from the outset that it can't end well (it is, after all, the basis for Romeo and Juliet and we all know how that ends).
Particularly notable in the film is the Oscar-nominated performance by Geoffrey Rush. Rush is Philip Henslowe, the owner of The Rose theater and the man for whom Shakespeare is writing Romeo and Juliet. Rush is, even when being tortured, laugh-out-loud funny. In Rush's hands, Henslowe's repeated insistence that everything will work out wonderfully for the play despite not having a clue how that will take place seems less delusional and more hard-won knowledge based on years of experience and more than one ulcer.