Our Favorite Tortured Poets

Happy Taylor-Swift-is-trying-to-kill-us — I mean, Tortured Poets Department Day. Swift’s surprise double album, seemingly largely inspired by her romances with actor Joe Alwyn and singer Matty Healy (with a few purported shoutouts to current, American Pie–loving boyfriend Travis Kelce), came out at midnight, and fans have been busy ever since soaking up every lyric, image, and Swiftly sigh within the 31 (!) songs. One thing is clear, though: The musician is far from the only tortured poet mentioned on this record.

And Swift and her exes are also far from the only painted artists to have graced our pop-culture landscape. Over the years, numerous films and TV shows have depicted struggling sonneteers and vexed versifiers, ranging from the real and acclaimed (see Shakespeare in Love) to the fictional and striving (see Dead Poets Society). Whether any of these onscreen poets inspired Swift’s latest album is unknown, but it’s safe to say the superstar stands among good, poetic company.

Allen Ginsberg

Seen in: Howl (2010); Kill Your Darlings (2013)

“I saw the best minds of my generation destroyed by madness.” And so starts Ginsberg’s iconic “Howl,” perhaps the best example of the Beat Generation poet’s brilliant and often-tortured mind. Over the course of his epic career, Ginsberg raged against the perils of conformity (a topic Swift has covered herself in songs like “The Outside”), capitalism, militarism, and more — as captured in numerous onscreen portrayals, most notably the middling 2010 film Howl (starring James Franco as the poet) and the flawed but far more watchable 2013 drama Kill Your Darlings (with Daniel Radcliffe taking on the role).

Kat Stratford

Seen in: 10 Things I Hate About You (1999)

As played to perfection by Julia Stiles, Kat Stratford was many things: a proud misfit, a lovestruck teen, a fashion icon, and, yes, a tortured poet. “I hate the way you’re always right / I hate it when you lie / I hate it when you make me laugh / even worse when you make me cry,” she read aloud to her classmates, before punching them (and viewers) in the gut with: “But mostly I hate the way I don’t hate you / not even close / not even a little bit / not even at all.” Sounds a bit reminiscent of the “I say, ‘I hate you,’ we break up, you call me, ‘I love you’” lines in “We Are Never Ever Getting Back Together,”,= doesn’t it?

Sylvia Plath

Seen in: The Bell Jar (1979); Sylvia (2003)

There’s maybe no poet more famously tortured than Plath, who suffered from major depression for most of her life until her death by suicide in 1963 — and whose writing bore some notable similarities to Swift’s. Plath’s struggles and achievements were depicted in 1979’s The Bell Jar, a much-maligned film named after the writer’s most famous book, and again in 2003’s Sylvia, an only slightly better movie starring Gwyneth Paltrow as Plath. If only the planned Kirsten Dunst–Dakota Fanning Bell Jar adaptation ever got made …

Lisa Simpson

Seen in: The Simpsons (1989–present)

Child prodigies are often tortured souls, and Lisa Simpson is a prime example. The forever-8-year-old constantly struggles to have her passions and talents taken seriously, including her poetry; in the 2006 episode “Moe’N’a Lisa,” she writes a poem on Moe’s wall, and the bar owner claims the work as his own and gets all the credit. Sure, she eventually forgives him, but only after feeling heartbroken about the betrayal, an emotion that post–Scooter Braun Swift has experienced herself. Someone give Lisa her flowers!

William Shakespeare

Seen in: Shakespeare in Love (1998)

Writer’s block, heartache, betrayal: just some of the many problems Swift covers in songs such as “The Story of Us” and “Bad Blood” and that a young Shakespeare (Joseph Fiennes) faced in the 1998 Oscar-winning comedy. Although the poet and playwright’s story (both in real life and the film) was not all doom and gloom, he was certainly no stranger to the occasional bout of psychological torture.

Paterson

Seen in: Paterson (2016)

If a character’s played by Adam Driver, you know he’s gonna be at least a little tortured. In this 2016 indie, Driver starred as a bus driver whose true love was poetry yet never shared his work with anyone but his supportive wife (sounds a bit like the scenario described in Swift’s “Sweet Nothing,” doesn’t it?). Some of Paterson’s distress came from his fretting over his poems’ quality, but a larger source of his frustration was a bit more unexpected: Marvin, his notebook-destroying bulldog.

Emily Dickinson

Seen in: Dickinson (2019–21)

Apple TV+’s dramedy series may not have always depicted its subject’s teenage life with the most accuracy (and some would say it was all the better for it!), but it did get a lot right, including young Dickinson’s frustration with gender norms, fascination with death, and oft-unrequited love. And through Hailee Steinfeld’s excellent performance, the poet — who just happens to be related to fellow writer Swift — and her tortured genius certainly made for compelling television.

John Keats

Seen in: Bright Star (2009)

Poor John Keats. Sure, he’s considered a legendary poet today (and probably inspired the line “take me to the lake where all the poets go to die” in Swift’s “The Lakes”), but during his too-short life, he suffered the loss of both of his parents, struggled financially, earned poor reviews for his poetry, and died of tuberculosis at age 25. Much of this psychological and physical torture was portrayed in Jane Campion’s 2009 romantic drama Bright Star, featuring Ben Whishaw as the writer and Abbie Cornish as Fanny Brawne, whom Keats loved but couldn’t commit to in part due to his lack of career success.

Neil Perry

Seen in: Dead Poets Society (1989)

You could argue that all the members of the Dead Poets Society (a club whose name many people are understandably confusing with The Tortured Poets Department) were tortured, due to the high expectations and strict ways of their New England prep school, but seemingly none suffered as much as Neil Perry. The passionate, ambitious senior (Robert Sean Leonard) wasn’t allowed to pursue his dreams by his difficult father, causing him so much distress that he ended his own life. It’s a tragic tale, but at least Neil got to experience the magic of poetry — and the freedom of creativity — during his time thanks to the mentorship of Robin Williams’s John Keating.

Jim Carroll

Seen in: The Basketball Diaries (1995)

The 1995 crime drama may not have earned the greatest reviews, but it did give baby Leonardo DiCaprio (who’d later be name-dropped in Swift’s “The Man”) a starring turn as a poetry-writing teen struggling with drug addiction and depression. Was the plot melodramatic and convoluted? Absolutely. But did it have a nice message that writing can help you cope with inner turmoil — similar to what Swift has said about Tortured Poets being a “lifeline”? One hundred percent.

Ezekiel “Books” Figuero

Seen in: The Get Down (2016–17)

During the one-season run of this Netflix musical-drama series, viewers got to meet Ezekiel, Zeke for short, a talented young poet living in 1997 New York who experienced his share of torture, including the death of his parents, the constant threat of violence, and a star-crossed romance akin to Swift’s classic “Love Story.” Despite solid reviews, The Get Down was cancelled before fans got to see how Zeke’s journey concluded, likely due to it being Netflix’s then-most-expensive series to date.

Ezra Fitz

Seen in: Pretty Little Liars (2010–17)

Ezra is better remembered by many Pretty Little Liars fans for his poor teaching methods and disregard for statuary rape laws, but he was also a (bad) poet with a whole lot of angst. Just take “B-26,” a poem he published about Aria that included the lines, “It’s a number / It’s a song / It’s a girl” and “Maybe bingo. / Lucky night? / Something says / It smells bad.” Hopefully Aria eventually wised up and saw that messed-up power dynamic for what it was, like Swift did in the powerful “Would’ve, Could’ve, Should’ve.”