In honor of the period drama's 20th anniversary on Dec. And its star-studded cast hasn't slowed down since the film won the best picture Oscar in 1999.įrom Pirates of the Caribbean to The Handmaid's Tale, the film's top-billed players - including Gwyneth Paltrow, Joseph Fiennes, Ben Affleck, Judi Dench and more - have enjoyed long careers spanning multiple projects in theater, movies and TV. It's been 20 years since John Madden's Shakespeare in Love, a comedy about a love affair in William Shakespeare's early years as a playwright, hit theaters.
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