THEN AND NOW: The cast of 'Shakespeare in Love'

gwyneth paltrow in shakespeare in love and in 2021 on jimmy kimmel
Gwyneth Paltrow starred in "Shakespeare in Love" when she was only 26.Miramax/HBO Max; Randy Holmes/ABC/Getty Images
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  • Gwyneth Paltrow, who turns 50 today, starred in "Shakespeare in Love" when she was only 26.

  • Paltrow won the Oscar for best actress for her role as Viola De Lesseps.

  • Colin Firth and Ben Affleck also starred in the critically-acclaimed 1998 film.

Gwyneth Paltrow starred as the main love interest of William Shakespeare, Viola De Lesseps.

gwyneth paltrow in shakespeare in love
Gwyneth Paltrow in "Shakespeare in Love."Miramax Films/HBO Max

Viola De Lesseps comes from a wealthy family but loves to watch Shakespeare's plays. Viola then disguises herself as a man named Thomas Kent to earn the part of Romeo in Shakespeare's first production of "Romeo and Juliet." Despite being betrothed to Lord Wessex, who she eventually marries and moves to America with, she falls in love with Shakespeare.

Gwyneth Paltrow is now a top Hollywood actress and the CEO of her own company.

gwyneth paltrow on jimmy kimmel in 2021
Gwyneth Paltrow in 2021.Randy Holmes/ABC/Getty Images

Throughout her lengthy career, Paltrow, 50, has received critical acclaim for her roles in films such as "Emma," "Great Expectations," and "Sliding Doors." She is also the CEO and founder of her own lifestyle brand, Goop. The company is worth an estimated $250 million.

Joseph Fiennes played William Shakespeare as he attempts to write and produce the first production of "Romeo and Juliet."

joseph fiennes in shakespeare in love
Joseph Fiennes in "Shakespeare in Love."Miramax Films/HBO Max

When we first meet Shakespeare, he's struggling to finish a play and is experiencing problems both financially and in his love life. After meeting Viola De Lesseps, she becomes his muse and he bases "Romeo and Juliet" on his blossoming romance with her.

Joseph Fiennes has since acted in "The Handmaid's Tale" and "American Horror Story."

joseph fiennes
Joseph Fiennes attends Hulu's "The Handmaid's Tale" Season 3 Finale on August 6, 2019.Harmony Gerber/FilmMagic/Getty Images

Fiennes, 52, is perhaps best known for his roles as Fred Waterford on Hulu's "The Handmaid's Tale," a role that he's held since 2017, and as Monsignor Timothy Howard on "American Horror Story: Asylum," which was released in 2012.

He is also set to appear in "The Mother" alongside Jennifer Lopez, which is currently in post-production and is expected to be released in May 2023.

Colin Firth plays Lord Wessex, Viola's fiancée and Shakespeare's biggest rival.

colin firth in shakespeare in love
Colin Firth in "Shakespeare in Love."Miramax Films/HBO Max

He is the main antagonist of the movie and is believed at one point to have orchestrated the death of Christopher Marlowe, thinking he was the one involved in an affair with Viola De Lesseps, though it is revealed that he was not. He constantly tries to keep Viola and Shakespeare apart.

He does not love Viola but is rather intent on marrying her so that he can use money from her wealthy family to settle his debts and start a new life with her in America.

Colin Firth is famous for his roles in movies like "Mamma Mia," "Love Actually," and the "Bridget Jones's Diary" trilogy.

colin firth
Colin Firth attends HBO Max's "The Staircase" New York Premiere at the Museum of Modern Art on May 3, 2022.Dia Dipasupil/WireImage/Getty Images

Firth, 62, earned both an Oscar and a Golden Globe for his leading role as King George VI in "The King's Speech."

Firth also went on to star in the "Kingsman" series and continued his role as Mark Darcy in the "Bridget Jones" sequel "Bridget Jones's Baby" in 2016. He also returned for "Mamma Mia! Here We Go Again" in 2018. His most recent acting credits include roles in "Empire of Light," "The Staircase," and "Mary Poppins Returns."

Judi Dench won an Oscar for her scene-stealing role as Queen Elizabeth I.

judi dench in shakespeare in love
Judi Dench in "Shakespeare in Love."Miramax Films/HBO Max

Queen Elizabeth is depicted as a mischievous lover of theater, and as having a biting sense of humor. She informs Lord Wessex that Viola De Lesseps has been "plucked," tipping him off to her and Shakespeare's affair. She later attends the performance of "Romeo and Juliet," and effectively pardons Viola and the theater company for allowing a woman to perform on the stage.

Judi Dench is one of the most famous British actresses, with iconic roles in the James Bond film series.

judi dench
Judi Dench attends press day at the RHS Chelsea Flower Show at The Royal Hospital Chelsea on May 23, 2022.David M. Benett/Dave Benett/Getty Images

In addition to her roles in "Skyfall" (2012), "No Time to Die" (2021), "Quantum of Solace" (2008), and multiple other James Bond films, Dench, 87, has held prominent roles in other period dramas such as "Pride and Prejudice" (2005) and "Jane Eyre" (2011).

Imelda Staunton plays a nurse entrusted with concealing Viola's affair with William Shakespeare.

imelda staunton in shakespeare in love
Imelda Staunton in "Shakespeare in Love."Miramax Films/HBO Max

She acts as Viola's constant companion and confidant and goes to great lengths to hide the fact that Shakespeare has been sneaking into Viola's chambers.

Imelda Staunton is perhaps best known for her role as Dolores Umbridge in the "Harry Potter" series.

imelda staunton
Imelda Staunton attends the world premiere of "Downton Abbey: A New Era" at Cineworld Leicester Square on April 25, 2022.Lia Toby/Getty Images

It was recently announced that Staunton, 66, would be taking over the role of Queen Elizabeth on "The Crown," which was previously acted by Claire Foy and Olivia Colman. Staunton is also well known for her role as Maud Bagshaw on the iconic British drama series "Downton Abbey."

Geoffrey Rush plays Philip Henslowe, the owner of the Rose Theatre.

geoffrey rush in shakespeare in love
Geoffrey Rush in "Shakespeare in Love."Miramax Films/HBO Max

In the film, Henslowe is in debt and constantly riding William Shakespeare to finish a crowd-pleasing play so that he can repay what he owes.

Geoffrey Rush is still acting and has starred in many iconic roles throughout his prolific career.

geoffrey rush
Geoffrey Rush attends the 56th Karlovy Vary International Film Festival on July 9, 2022.Gabriel Kuchta/Getty Images

Rush, 71, is best known for his role as Captain Hector Barbossa in the "Pirates of the Caribbean" films, as well as his role as Hans Hubermann in "The Book Thief" (2013) and Lionel Logue in "The King's Speech" (2010). He also won the Oscar for best actor for his leading role in the 1996 film "Shine."

Rush is also among 24 people who have won the "Triple Crown of Acting," having won an Academy Award, a Primetime Emmy Award, and a Tony Award.

Tom Wilkinson plays Hugh Fennyman, the financial backer of the Rose.

tom wilkinson in shakespeare in love
Tom Wilkinson in "Shakespeare in Love."Miramax Films/HBO Max

He oversees the production and is elated when Shakespeare offers him a role as the Apothecary in his production of "Romeo and Juliet."

Tom Wilkinson is also still acting.

tom wilkinson
Tom Wilkinson attends the "Belgravia" photocall at Soho Hotel on February 17, 2020.Mike Marsland/WireImage/Getty Images

Wilkinson, 74, has received multiple accolades for his acting career, including two Academy Award nominations. His most recent acting credits include roles in "Belgravia" (2020), "Watership Down" (2018), and "The Kennedys" (2011).

Martin Clunes plays Richard Burbage, a famous actor and the owner of the rival Curtain Theatre.

martin clunes in shakespeare in love
Martin Clunes in "Shakespeare in Love."Miramax Films/HBO Max

He is also the husband of Rosaline, who is involved with William Shakespeare at the start of the film. When he learns of their affair, he attempts to kill Shakespeare.

However, they resolve their feud. After Viola is exposed as a woman on the stage, forcing the theater to close for indecency, he even offers the Curtain to Will for his performance of "Romeo and Juliet."

Martin Clunes is best known for playing Martin Ellingham in "Doc Martin" and Gary Strang in "British Men Behaving Badly."

martin clunes
Martin Clunes on September 18, 2019.J. Almasi/GC Images/Getty Images

Clunes, 60, is a well-known actor in the UK and is known for his roles in "Manhunt" (2019-2021) "Warren" (2019), and "Vanity Fair" (2018).

Ben Affleck plays Ned Allen, one of the actors in "Romeo and Juliet."

ben affleck in shakespeare in love
Ben Affleck in "Shakespeare in Love."Miramax Films/HBO Max

He takes his role as Mercutio very seriously and is suspicious of Shakespeare and Thomas Kent's relationship.

Ben Affleck remains one of the top actors in Hollywood, thought he's also now a respected producer.

Ben Affleck in a dark suit
Ben Affleck.Arturo Holmes/Getty

After "Shakespeare in Love," Affleck, 50, went on to star in films such as "Deep Water" (2022), "The Accountant" (2016), and "Gone Girl" (2014).

In May 2021, Affleck and ex-fiancée Jennifer Lopez sparked dating rumors following her high-profile split from Alex Rodriguez. The pair were engaged by April 2022 and exchanged marriage vows three months later.

Rupert Everett plays the small role of Christopher Marlowe, another writer of the time.

rupert everett in shakespeare in love
Rupert Everett in "Shakespeare in Love."Miramax Films/HBO Max

In "Shakespeare in Love," it is implied that Marlowe gives the idea of the plot for "Romeo and Juliet" to his friend William Shakespeare. He dies in a bar fight, though Shakespeare believes he is responsible for his friend's death after telling Lord Wessex that Marlowe and Viola were having an affair.

Rupert Everett is still well known for his role as George Downes in "My Best Friend's Wedding."

rupert everett
Rupert Everett attends the "My Policeman" premiere during the 2022 Toronto International Film Festival.Amy Sussman/Getty Images

The British actor also acted alongside his "Shakespeare in Love" costar Colin Firth in "The Happy Prince" (2018), which chronicled the life of poet and playwright Oscar Wild. He also wrote and directed the film, which received a Satellite award for best first feature.

Everett, 63, is also slated to appear in the upcoming drama "My Policeman," which stars Harry Styles and Emma Corrin.

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