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Best picture Series — Shakespeare in Love (1998) Review

12/12/2025

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Evan D.

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As a project this year we are taking a trip through time to revisit all of the Best Picture winners in history, Wings to Anora. Shakespeare in Love is the seventy-first film in that series, to see all the other Best Picture reviews, click here.

As chronicled in our Best Picture review for Hamlet, William Shakespeare’s works have served inspirational to film history from its very earliest days. So too has his life and legend it seems. Just this year a fictionalized account of his son’s death, Hamnet, has brought audiences across the country to tears. Who is to say if that tale of the Bard’s personal life can go the distance, but if it does, it won’t be the first time. That honor would go to John Madden’s Shakespeare in Love.

It’s the late 16th century and William Shakespeare (Joseph Fiennes) is flitting across London, striking up romance with any pretty girl that crosses his path. He has promised a play to Philip Henslowe (a delightfully pitiful Geoffrey Rush,) a comedy he’s calling Romeo and Ethel, the Pirate King’s Daughter. Unable to work through heartbroken writers block, he finds sudden inspiration in the person of Viola De Lesseps (Gwyneth Paltrow,) a luminous young noblewoman enraptured by poetry and Shakespeare’s own work. Little does Will know, but Viola has disguised herself as a man to win a part in his latest play. The fiery romance struck up between the pair begins to show itself in Shakespeare’s suddenly prolific writing. 

To call Shakespeare in Love at all biographical would be a gross misrepresentation. Rather it uses Shakespeare’s most famous works as a basis for a period romantic comedy. The dingy streets of 1500s London are anything but here, alive with color and the bustle of folks eager to see a good show. Little is said of Will’s wife and kids back home and his life as depicted here hews more closely to one of his comedies than any sort of reality. 

Shakespeare in Love is a film that works better the less seriously you take it. There is some joy to be had in seeing Paltrow do She’s the Man in 1592 or Ben Affleck agreeing to play a small role in Romeo and Juliet because he thinks Mercutio is the lead. The camaraderie of the players, the bumbling foolishness of the financiers and whatever Colin Firth is up to as Lord Wessex all provide broad comedy. If nothing else, the film is entertaining in spurts.

Unfortunately, Madden’s movie is also packed with faults. The plot litters itself with Shakespeare references and winks or nods to other historical figures. Threading these Easter eggs the tone of the film clearly thinks itself far more clever than the actual content deserves. By pitching itself as something more than a relatively standard rom-com it overplays its hand. 

Similarly, Joseph Fiennes seems unequipped to tackle any depth his Shakespeare may otherwise have had in more capable hands. Story goes that Daniel Day-Lewis was preferred for the part and its hard to imagine the same film surrounding him. Fiennes is energetic in his portrayal but not particularly believable as either Shakespeare nor being in love. Still, Paltrow is quite entertaining in her dual role of Viola and her alias Thomas Kent. Her character’s passion for the writing comes through and by far she is the best of the bunch at conveying the classic soliloquies of Romeo and Juliet. 

I always hold a soft spot for films that are made with such earnestness and conviction that any small faults or indulgences melt away. Many movies, many Best Pictures even, fit this bill but Shakespeare in Love just is not one. It’s a picture that thinks itself above the middle-brow comedy it ultimately is. Rather than sincerity there’s a smugness. The comedy does work at times but it’s never allowed to fully embrace how silly it is. 6/10
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