The Cast of 'Shakespeare in Love,' Then and Now

8:30 AM 12/3/2018

by Christi Carras

Twenty years after the film hit theaters, Gwyneth Paltrow, Joseph Fiennes and more from the best picture Oscar winner have added several projects to their resumes.

1998 - "Shakespeare in Love" - H 2016

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. And its star-studded cast hasn't slowed down since the film won the best picture Oscar in 1999. 

From 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. 

In honor of the period drama's 20th anniversary on Dec. 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.

  • Gwyneth Paltrow

    Paltrow received the 1999 best actress Oscar for her Shakespeare in Love role as leading woman Viola De Lesseps, with whom Fiennes' Shakespeare falls in love while writing his classic romance Romeo and Juliet. Though the actress had already been featured in films like Jane Austen's Emma, David Fincher's Se7en and the 1998 thriller A Perfect Murder, Shakespeare in Love established Paltrow as an Academy darling. Since her Oscar win, Paltrow has gone on to star in films and TV series like The Talented Mr. Ripley, The Royal Tenenbaums, the Iron Man franchise, Contagion, Glee and most recently Avengers: Infinity War, reprising her role as Iron Man's righthand woman Pepper Potts. Next, she's set to star in The Politician, a new series from Ryan Murphy, and the latest untitled Avengers installment. 

  • Joseph Fiennes

    Fiennes scored his breakout role in Shakespeare in Love as the title character, portraying the world's most famous playwright and tortured genius in the throes of desire. The film was just one of many period and Shakespearean projects in which Fiennes starred before and after, including the Cate Blanchett starrer Elizabeth, the World War II drama Enemy at the Gates, Luther, The Merchant of Venice and the TV series Camelot. More recently, the actor has been known for his roles in series like the "Asylum" season of FX's American Horror Story and Hulu's The Handmaid's Tale, for which he received a 2018 supporting actor Emmy nomination for his work as the misogynistic Fred Waterford. He is set to return as Fred in the third season of the dystopian drama, slated to premiere in 2019.

  • Geoffrey Rush

    Rush was no stranger to Shakespeare or Oscar recognition by the time received a supporting actor nomination for playing jaded Rose Theater owner Philip Henslowe in Shakespeare in Love. He had already secured a best actor Oscar for his work in the David Helfgott biopic, Shine, the year prior, and before that, he participated in a film adaption of Shakespeare's Twelfth Night. After co-starring with Fiennes both in Shakespeare in Love and in Elizabeth, Rush went on to appear in films like Frida, Finding Nemo and the Pirates of the Caribbean franchise, as well as Quills and The King's Speech, which both earned him two more Oscar noms. Most recently, the actor reprised his role as Captain Barbosa in Pirates of the Caribbean: Dead Men Tell No Tales and portrayed Albert Einstein in National Geographic's Genius, for which he received a Golden Globe nomination. His next appearance will be Shawn Seet's family drama Storm Boy.

  • Colin Firth

    Before Firth and Rush teamed up for Oscar gold in 2010's The King's Speech, they joined forces in Shakespeare in Love, with Firth starring as Viola's betrothed, the aristocratic Lord Wessex. But like many in the cast, Firth was already a period veteran by then, having appeared in series and films like Nineteen Nineteen, The English Patient and Jane Austen's Pride and Prejudice. His work has since spanned multiple genres, from romantic comedies like Love Actually, Mamma Mia! and the Bridget Jones franchise to more period pieces like his Oscar-winning turn as King George VI in The King's Speech. Most recently, he reprised his role as Harry in Mamma Mia! Here We Go Again and starred in the French drama Kursk. Soon, he is set to appear in Disney's Mary Poppins Returns alongside Emily Blunt and Lin-Manuel Miranda, as well as in Marc Munden's The Secret Garden.

  • Ben Affleck

    1998 was a major year for Affleck, who starred as seasoned thespian Ned Alleyn in Shakespeare in Love shortly before he collected a Golden Globe and an Oscar for his work with Matt Damon on Good Will Hunting. Unlike many of his co-stars, the period film was a departure from Affleck's typical fare. Since Shakespeare in Love, Affleck has added several acting, directing and producing credits to his name, including Pearl Harbor, DC's latest Batman franchise, Gone Girl and Argo, which nabbed Affleck the 2013 best picture Oscar. He most recently starred as Batman in DC's Justice League, while his next role is in the crime drama Triple Frontier.

  • Judi Dench

    Shakespeare in Love did not mark Dame Dench's first Shakespearean role, or even her first role as a queen. Before she portrayed Queen Elizabeth in the period comedy, Dench played Queen Victoria in 1997's Mrs. Brown and starred in several adaptions of Shakespeare plays, including Hamlet, A Performance of Macbeth and The Comedy of Errors. Since nabbing a supporting actress Oscar for Shakespeare in Love, Dench has received five more Oscar nominations from 2000's Chocolat to 2013's Philomena. Recently, she starred in the Agatha Christie-inspired murder mystery Murder on the Orient Express, while her next appearance will be in a film adaptation of the hit young adult novel Artemis Fowl.