Gwyneth Paltrow, Shakespeare in Love

Laurie Sparham/Miramax/Universal/Kobal/Shutterstock

Hopeless romantics, this one's for you. 

In case you didn't already know, December is a month of love, magic and of course, Christmas. While this post has nothing to do with Christmas it does have to do with love and the magic of William Shakespeare, because today marks the 20th anniversary of Shakespeare in Love.

20 years ago in December—the drama film was released on Dec. 11, 1998 in the U.S.—Shakespeare in Love first hit theaters and it was pure magic.

Did you really think a story about Will Shakespeare (Joseph Fiennes) and his muse (played by Gwyneth Paltrow) would be anything other than romantic?

In case you want a little refresher, the romance film tells the story of a young Will Shakespeare who falls in love with Viola de Lesseps (Paltrow) after she tries to audition for a part in his play under a male name, because women were not allowed to act in those days, duh.

Despite being a struggling poet and playwright, Viola also falls for Will, even though he's married and she's promised to Lord Wessex (Colin Firth). As the two fall deeper and deeper in love, their romance inspires Will to write one of his greatest masterpieces...Romeo and Juliet.

Romance, make believe, drama, beautiful costumes and forbidden love, what more could you want from a film?

In honor of Shakespeare in Love's 20th anniversary, we're shining a light on all of Paltrow's best roles over the years. After all, she did win an Academy Award for this character, and based on the fact that we still love watching her as Viola, she definitely deserved it.

What are you waiting for? Raise your goblets of wine, toast to Shakespeare and his brilliance and start scrolling through all of Paltrow's iconic roles below.

Gwyneth Paltrow, Hook

TriStar Pictures

In 1991, Gwyneth Paltrow had a small role in Hook as young Wendy Darling in the flashback clips of Peter Pan's (Robin Williams) life.

Gwyneth Paltrow, Moonlight And Valentino

Moviestore Collection/Shutterstock

After Rebecca Trager Lott (Elizabeth Perkins) loses her husband in a freak accident she turns to three woman for support. Her best friend Sylvie Morrow (Whoopi Goldberg), her sister Lucy Trager (Paltrow) and ex-stepmother Alberta Trager (Kathleen Turner) all help her get back on her feet and in the process they meet a handsome house painter who they nickname "Valentino."

Gwyneth Paltrow, Emma film

David Appleby/Matchmaker/Miramax/Kobal/Shutterstock

Stemming from Jane Austen's memorable tale, Emma tells the story of Emma Woodhouse (Paltrow), a young woman in 19th century England who loves meddling in other people's love lives and trying to be their very own matchmaker. Along the way she muddles up relationship after relationship of her own and has no clue that she's even doing it.

Gwyneth Paltrow, Ethan Hawke, Great Expectations


Based on the classic Charles Dickens tale, Great Expectations gets an update with Finn (Ethan Hawke), a painter in New York City, who tries his entire life to get the woman of his dreams, Estella (Paltrow), to fall in love with him.

Gwyneth Paltrow, A Perfect Murder

Moviestore Collection/Shutterstock

After discovering his wife (Paltrow) is having an affair, Steven Taylor (Michael Douglas) hires his wife's lover (Viggo Mortensen) to kill her in what appears to be the perfect murder...or is it?

Gwyneth Paltrow, Hush

Peter Iovino/Columbia Tristar/Kobal/Shutterstock

In this 1998 thriller, Paltrow plays Helen, the young girlfriend of Jackson Baring (Johnathon Schaech). The two eventually get married and Helen becomes pregnant, but things change when she moves to his family's farm where his mother Martha (Jessica Lange) lives. She wants to keep the baby, to get ride of Helen, and to have her son all to herself.

Shakespeare in Love, Gwyneth Paltrow


Paltrow won the Oscar for Best Actress in a Leading Role for her portrayal of Viola de Lesseps in Shakespeare in Love and it's a role we will never forget. When a young Will Shakespeare (Joseph Fiennes) is simply a struggling poet and playwright, he meets Viola, who turns out to be his one true love. While discovering their love story, he is inspired to write one of his most iconic plays, Romeo and Juliet. The film also stars Colin Firth, Ben Affleck, Judi Dench and Geoffrey Rush.

Gwyneth Paltrow, The Royal Tenenbaums

James Hamilton/Touchstone/Kobal/Shutterstock

Wes Anderson's The Royal Tenenbaums is one of Paltrow's most iconic roles to date. In the film, the blonde beauty plays sister Margot Tenenbaum, who is a grown prodigy like her brothers Chas (Ben Stiller) and Richie (Luke Wilson). Within the movie the trio is seen under the same roof as their mother Etheline (Anjelica Huston) while their father Royal (Gene Hackman) tries to come back into their lives and make things right. The film also features Owen Wilson and Bill Murray.

Gwyneth Paltrow, Shallow Hal

Moviestore Collection/Shutterstock

Hal (Jack Black) only dates women who are physically beautiful, until he's hypnotized into recognizing only the inner beauty of women. This leads to him falling for Rosemary (Paltrow), who is obese in reality, but Hal only sees as a perfect woman because of how wonderful she is on the inside. The trick is whether or not the relationship will last once he's no longer hypnotized. 

Iron Man, Gwenyth Paltrow, Onscreen Assistants

Industrial Light & Magic

In 2008, Paltrow became Pepper Potts for the first time in the Marvel film Iron Man. Pepper is Tony Stark's (Robert Downey Jr.) personal assistant in this film and one of the first people to learn of his identity as Iron Man when he returns from being held captive in Afghanistan. While a prisoner, Tony creates a weaponized suit of armor to fight evil, which leads to him becoming a hero among men.

Gwyneth Paltrow, Iron Man 2

Paramount Pictures

After revealing his real identity in the first film, Tony Stark (Downey) must deal with the pressures of being Iron Man, while his health declines due to poisoning from palladium in his arc reactor, all while trying to shut down a mad man who is linked to his father's legacy. Oh, and Pepper (Paltrow) is the new CEO of Stark International in the sequel, but later tries to renounce her title due to stress and almost dying, but is cut off by Tony, who kisses her marking the beginning of their romance.  

Gwyneth Paltrow, Tim McGraw, Country Strong, Country Movies

Sony Pictures

In 2011, Paltrow showed off her musical chops and went a little country while playing Kelly Canter in Country Strong. The drama tells the story of fallen star Kelly, who meets a country songwriter named Beau (Garrett Hedlund) while in rehab. Once out of rehab she goes back on the road to try and stage a comeback with her husband and manager (Tim McGraw) leading the way and Beau and a new up and coming artist named Chiles (Leighton Meester) as her openers.

Gwyneth Paltrow, Glee


From 2010 to 2014, Paltrow had a recurring role on Glee as Holly Holliday. Holly is introduced as a substitute teacher who takes over the glee club when Will Schuester (Matthew Morrison) is out sick. The two later have a brief romance before she leaves town for another job.

Gwyneth Paltrow, Contagion

Warner Bros/Kobal/Shutterstock

Beth Emhoff (Paltrow) returns from a business trip in Hong Kong with some sort of infection that quickly spreads by touch and creates panic in America as the doctors and administrators from the U.S. Centers for Disease Control begin to fear they have an epidemic on their hands. With only Beth's husband (Matt Damon) seeming to be immune to the virus or disease, it begins to spread and panic ensues. 

Gwyneth Paltrow, The Avengers

Marvel Studios

In 2012, Paltrow reprised her role as Iron Man's (Downey) right hand and girlfriend, Pepper Potts for The Avengers. In this superhero film, the world's biggest heroes team up to fight and stop Loki (Tom Hiddleston) from enslaving humanity.

Iron Man 3

Marvel/Walt Disney Pictures

As Tony Stark's (Downey) life starts to unravel at the hands of an enemy who destroys his personal world, he will do anything to keep his loved one, Pepper Potts (Paltrow) safe, and that means revenge is on the menu. In addition to Tony AKA Iron Man seeking revenge, and discovering if he can win without all of his suits as weapons, Pepper gets kidnapped, injected with Extremis and eventually kills a massive villain. 


Gwyneth Paltrow, Spider-Man: Homecoming

Marvel Studios

Pepper Potts (Paltrow) makes an appearance in Spider-Man: Homecoming—the movie follows Peter Parker (Tom Holland) as he balances life as a high school student and as Spider-Man while being mentored by Tony Stark (Downey)—and fans get to see that she is in fact still with Tony and the two are planning to get engaged.

Gwyneth Paltrow, Avengers: Infinity War

Marvel Studios

In 2018, fans once again saw Paltrow as Pepper Potts (briefly) as she and Tony (Downey) run in Central Park and talk about their future children before he goes into superhero mode. We later see her again when Tony is aboard one of Thanos' Q-Ships and she begs him to get off the ship and come back to her, but their transmission is cut off. While we don't know what's next for Pepper and Tony, we do know that in Avengers: Infinity War, the Avengers and their allies sacrifice everything in hopes of defeating Thanos (Josh Brolin) before he ends the universe...but are they successful?

Make sure to vote for your favorite role by the Los Angeles native in our poll now and then re-watch Shakespeare in Love immediately! 

It'll make you believe in love once again, trust us. The story of Romeo and his love Juliet is tragic, but full of love, while Shakespeare in Love is just as romantic, but not as tragic, so it's a win-win.

Gwyneth Paltrow's Best Roles
Which of Gwyneth Paltrow's roles is most iconic?
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