Cover There’s a new Shakespeare in town! Irish actor Paul Mescal brings all the "Sad Boy" energy to the 16th century playing the bard in 2025's Hamnet. (Photo by Rob Kim/WireImage)
There’s a new Shakespeare in town! Irish actor Paul Mescal brings all the "Sad Boy" energy to the 16th century playing the bard in 2025's Hamnet. (Photo by Rob Kim/WireImage)
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From period-drama heartthrobs to chaotic "true-crime" conspiracies, we’re looking at the big-screen portrayals of Shakespeare that turned the world’s most famous writer into a total main character.
April 23rd marks the birthday of the world’s most famous playwright, and while we all suffered through Macbeth in high school, Hollywood has spent decades trying to make the man behind the quill look, well, a bit more like a leading man. Whether he’s being played by an Oscar-nominee in a ruff or a comedian in a wig, "Will" has become a character in his own right—and honestly, the vibes range from "TikTok main character energy" to "Tumblr’s favorite sad boy."
Pro-tip: If you’re an actress looking for an Oscar, just play William’s love interest. Between Gwyneth Paltrow and Jessie Buckley, the role of "Shakespeare’s Muse" is officially the luckiest gig in Hollywood.
1. The "Sad Boy" Shakespeare
The Actor: Paul Mescal
The Movie: Hamnet (2025)
Playing Shakespeare as a… Sad, weepy boy that rivals Hamlet himself contemplating a skull in the rain
Who plays Anne? Jessie Buckley (playing Agnes/Anne)
If you thought Paul Mescal peaked in "devastatingly beautiful grief" during Aftersun, think again. In this adaptation of Maggie O'Farrell’s hit novel, Mescal plays a father haunted by the death of his son. It’s less "writing comedies" and more "staring at the English countryside while the score makes you cry."
The Oscar Connection: Jessie Buckley just took home the Best Actress Oscar for this role last March, proving the "Shakespeare Muse" luck is still going strong!
Read more: What Paul Mescal reads: 5 book recommendations from the 'Hamnet' star, from Rooney to Carver
Above While Mescal is now the face of the "Sad Bard," he almost wasn't! He was deep in rehearsals for a stage production of "A Streetcar Named Desire' when he got the call for this film. He’s essentially gone from playing a 20th-century icon (Stanley Kowalski) to the ultimate 16th-century icon in the span of a single awards season.
2. The "Heartthrob" Shakespeare
The Actor: Joseph Fiennes
The Movie: Shakespeare in Love (1998)
Playing Shakespeare as a… Romantic lead that rivals Romeo under a balcony with significantly more chest hair and eyelashes we all dream to have
Who plays Anne? Anne is back in Stratford; Will is busy wooing Gwyneth Paltrow (as Viola de Lesseps)
This is the movie that convinced a generation of Millennials that Shakespeare was a total babe with a leather jacket and serious writer's block. He spends half the movie running through 16th-century London and the other half inventing the most famous plays in history as "inside jokes" for his girlfriend.
The Oscar Connection: Gwyneth Paltrow famously won Best Actress for this, and Judi Dench won Best Supporting Actress for her 8-minute cameo as Queen Elizabeth I.
Above This role was almost a total "What If?" for Hollywood history. Before Joseph Fiennes was cast, Julia Roberts was set to play the lead role—but she famously insisted that the only person who could play her Shakespeare was Daniel Day-Lewis. When he turned it down, the project actually collapsed for several years until Fiennes and Paltrow eventually saved it.
3. The "Imposter" Shakespeare
The Actor: Rafe Spall
The Movie: Anonymous (2011)
Playing Shakespeare as a… Drunken fraud that rivals a chaotic TikTok influencer taking credit for a viral sound
Who plays Anne? This movie skips the wife and focuses on the "real" author, the Earl of Oxford (Rhys Ifans)
In this wild "conspiracy theory" flick, Shakespeare isn't a genius—he’s a semi-literate, loud-mouthed actor who blackmails the actual writer to get his name on the posters. Rafe Spall plays him with delightful, messy energy. It’s the ultimate "fake it 'til you make it" performance.
Read more: Brutus is just as cute as Caesar! Did you know that these 5 movies are inspired by Shakespeare?
Above Director Roland Emmerich is known for blowing up the White House in 'Independence Day', so it makes sense that his take on Shakespeare was an "explosive" conspiracy theory. To play this illiterate, drunken version of Will, Rafe Spall reportedly leaned into the "rockstar" excess of the London stage, treating the Globe like a chaotic dive bar.
4. The "Legend" Shakespeare
The Actor: Kenneth Branagh
The Movie: All Is True (2018)
Playing Shakespeare as a… Retired dad that rivals King Lear trying to fix a garden instead of a kingdom
Who plays Anne? The legendary Judi Dench
Branagh has played every Shakespearean role under the sun, so he finally decided to play the man himself. This is "Grandpa Will"—he’s moved back to Stratford, his theater burned down, and he’s wearing a prosthetic nose that deserves its own IMDb credit. It’s a quiet, cozy look at the Bard’s final act.
Above Branagh is the king of the "Shakespeare Cinematic Universe." His splashy 1989 'Henry V'—made when he was just 28!—basically opened the floodgates for Shakespeare to be a cinematic staple again. Before that film's massive success, Hollywood thought Shakespeare was "box office poison." Branagh single-handedly made the ruff cool again.
5. The "Relatable" Shakespeare
The Actor: David Mitchell
The Show: Upstart Crow (2016–2020)
Playing Shakespeare as a… Stressed-out middle manager that rivals Malvolio on a very bad "yellow stockings" day
Who plays Anne? Liza Tarbuck
Ever wonder if Shakespeare complained about the high cost of London rentals or the annoying commute on the stagecoach? David Mitchell plays Will as a fussy, brilliant, and slightly arrogant writer just trying to balance his "genius" status with a chaotic family life. It’s basically The Office, but with parchment.
Above This show was written by Ben Elton, the comedy genius behind 'Blackadder'. One of the best running gags is that Will is constantly "inventing" famous phrases that we use today—only for his family to tell him they’re "a bit wordy" and will never catch on.
6. The "Rockstar" Shakespeare
The Actor: Laurie Davidson
The Show: Will (2017)
Playing Shakespeare as a… Punk-rock poet that rivals a young Orsino at a Coachella afterparty
Who plays Anne? Maya Arad-Yasur
If you like your history with a side of glitter and a synth-pop soundtrack, this is for you. This version of Will arrives in London with big dreams and has a "main character" complex. It’s vibrant, loud, and treats the Globe Theatre like a mosh pit.
Above This was Laurie Davidson’s first-ever professional role after graduating from drama school. He beat out hundreds of actors for the part of the "Rockstar Will" because the directors felt he had the "electric" energy of a modern-day musician arriving in the big city for the first time.
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Karen Vera is the regional content director for Tatler Asia. Having led editorial strategy across Hong Kong, Singapore, Manila, Jakarta, and Shanghai throughout her career, she is a devoted culture vulture whose favorite party trick is naming every Oscar Best Picture winner from 1972 onwards. (Annie Hall won in 1977, by the way.)
