3, The Hollywood Reporter takes a look at how the careers of its lead and supporting castmembers have flourished in the form of Oscar wins, Emmy nominations and more recognition for their growing bodies of work, as well as at their future projects. 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. Paltrow and Affleck dated from 1997 to 2000, and during the course of their relationship the couple starred together in Shakespeare in Love and Bounce. 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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