25 Years Later: 10 Rare And Iconic '10 Things I Hate About You' Photos That Still Define '90s Teen Romance

Two and a half decades later, the enduring appeal of 10 Things I Hate About You remains as potent as Kat Stratford’s signature snark. Released in 1999, this romantic comedy is the quintessential '90s teen film, brilliantly adapting Shakespeare’s The Taming of the Shrew for a modern high school setting. As of the current date, the film is celebrating its 25th anniversary, bringing a fresh wave of nostalgia and previously unseen photos to the surface, reminding fans why the chemistry between Heath Ledger’s Patrick Verona and Julia Stiles’ Kat is timeless.

The film’s visual legacy—from the grunge-meets-preppy fashion to the instantly recognizable locales of Padua High School—is preserved in a treasure trove of photos. Beyond the famous movie stills, the 25th anniversary has sparked a renewed interest in rare, behind-the-scenes Polaroids and recent cast throwbacks, offering a unique glimpse into the making of a classic. We dive into the most iconic and recently unearthed photos that continue to shape the film's cult status.

The Iconic Cast: Then and Now

The success of 10 Things I Hate About You is inseparable from its stellar ensemble cast, many of whom were on the cusp of major stardom. The film served as a launchpad for several actors who have since achieved tremendous success in Hollywood.

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• Julia Stiles (Kat Stratford): The fiercely independent, feminist protagonist. Her role as Kat cemented her status as a formidable young actress.
• Heath Ledger (Patrick Verona): The mysterious "bad boy" from Australia. This was his first American film role, and his performance is now legendary.
• Joseph Gordon-Levitt (Cameron James): The sweet, earnest newcomer. The film was an early step in his transition from child actor to leading man.
• Larisa Oleynik (Bianca Stratford): Kat’s popular, rules-following younger sister.
• David Krumholtz (Michael Eckman): Cameron's best friend and strategic mastermind.
• Andrew Keegan (Joey Donner): The shallow, narcissistic model who wants Bianca.
• Gabrielle Union (Chastity Church): Bianca's best friend.
• Larry Miller (Walter Stratford): Kat and Bianca's overprotective obstetrician father.

The 10 Most Defining Photos and Moments from the Cult Classic

These photos, ranging from candid on-set moments to unforgettable cinematic stills, capture the heart and soul of 10 Things I Hate About You and have seen a surge in popularity around the film's 25th anniversary.

1. The Grandstand Serenade: Heath Ledger's Iconic Moment

The photo of Patrick Verona (Heath Ledger) running down the stadium steps, attempting to win Kat back by singing Frankie Valli’s "Can't Take My Eyes Off You" over the loudspeaker, is arguably the most famous still from the movie. This scene, shot at Stadium High School in Tacoma, Washington, is a perfect blend of grand romantic gesture and teen embarrassment, and the photo captures Ledger's raw, charismatic energy that propelled him to fame. Director Gil Junger noted that Ledger was nervous about the scene, but his natural talent shone through.

2. The Rare Polaroid Snaps: Behind-the-Scenes Fun

One of the freshest photo discoveries for fans are the candid Polaroid pictures taken on set. These rare photos offer a truly unique, unfiltered look at the cast's chemistry off-camera. They often feature the young stars—Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, and Larisa Oleynik—hanging out, goofing off, and relaxing between takes. These images highlight the genuine camaraderie that translated so well to the screen, making the film feel authentic rather than manufactured.

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3. Julia Stiles' Emotional Poem Reading

The photo of Kat Stratford reading her famous poem, "10 Things I Hate About You," in class is a powerful cinematic moment. The close-up shot captures Julia Stiles' genuine tears and vulnerability, a moment that was reportedly not entirely scripted. Stiles delivered the performance with such emotional honesty that it became the defining scene for her character and a major highlight of the film’s emotional depth.

4. The Prom Dance: Kat and Patrick's First Slow Dance

A beautiful photo from the prom scene captures Kat and Patrick finally sharing a moment of quiet connection on the dance floor. This is a crucial visual entity, representing the payoff of their tumultuous relationship. The scene is noted for its subtle tension and the shift from their initial animosity to true affection, all while wearing iconic late '90s formal wear.

5. Joseph Gordon-Levitt's Anniversary Throwback

In a nod to the film's anniversary, Joseph Gordon-Levitt (Cameron) often shares a throwback photo from the set. These social media posts, which surface around the anniversary date, are a great source of current, fresh content for fans. The photos usually feature him alongside his co-stars, providing a heartwarming reminder of the young cast’s early days together.

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6. The Band Mandella on the Rooftop

The photo of the band Mandella (a real-life band named Letters to Cleo) performing on the roof of Padua High School is an iconic visual from the film's climax. This image perfectly encapsulates the film's blend of Shakespearean drama with '90s alternative rock culture. The band performing "I Want You to Want Me" is a unique visual element that ties the movie to its specific time period.

7. The Paintball Scene

The photo of Kat and Patrick enjoying a chaotic, paint-splattered day of paintball is a fan favorite. This visual represents the turning point where Kat finally lets her guard down and accepts Patrick’s genuine affection. It's a key photo that symbolizes their unconventional courtship, far removed from typical teen movie clichés.

8. The Stratford Sisters' First Photo Together

A classic movie still of Kat and Bianca Stratford (Julia Stiles and Larisa Oleynik) in their home is a foundational visual. It immediately establishes the contrast between the two sisters—Kat in her grunge attire and Bianca in her pastel, feminine look—reflecting their opposing personalities and the central conflict of the film, which is based on the relationship between Shakespeare's Katherine and Bianca.

9. The '90s Fashion: Kat's Army Pants and Crop Top

Photos of Kat’s wardrobe, particularly her iconic combination of army-green cargo pants, a simple crop top, and chunky boots, are essential visual entities. These images are constantly referenced in fashion nostalgia articles, highlighting the film’s influence on '90s and early 2000s style. The photos showcase the timeless "rebel chic" look that Kat popularized.

10. The Cast Then and Now Photo Grid

The 25th anniversary has made "then and now" photo grids extremely popular. These images juxtapose the youthful cast from 1999—including Heath Ledger, Julia Stiles, and Gabrielle Union—with their current, successful selves. These photos serve as a powerful visual timeline, celebrating the film's lasting impact and the careers it launched.

The Lasting Legacy of Padua High School (Tacoma)

Many of the most memorable photos from the film are tied to the actual shooting locations, primarily Stadium High School in Tacoma, Washington, which served as the exterior for the fictional Padua High. Photos of the school’s unique, castle-like architecture are instantly recognizable to fans, providing a dramatic, almost theatrical backdrop for the teen drama. The iconic grandstand where Patrick sings to Kat is a real-life location that fans continue to visit and photograph, keeping the film's visual identity alive.

The film’s enduring popularity, especially visible through the anniversary photo releases and cast reflections, confirms its status as more than just a teen movie. It’s a smart, witty, and emotionally resonant adaptation that continues to charm new generations. Whether you are revisiting the classic stills or discovering a rare Polaroid, the photos of 10 Things I Hate About You are a vibrant testament to a perfect piece of late '90s cinema.