26 years after releasing in theaters, Heath Ledger’s cult classic teen comedy with a Shakespearean twist is a streaming hit on Prime Video.

Ledger became truly legendary with his performance as the Joker in Christopher Nolan’s The Dark Knight, winning a posthumous Academy Award for his take on that most fascinating of Batman villains.

Though he is most ᴀssociated with dramatic roles, thanks to movies like Dark Knight, Brokeback Mountain and others, Ledger did find his way into a couple of lighthearted comedies. 2001’s A Knight’s Tale may have been set in medieval times, but its tone was not as solemn as its subject matter might indicate.

Two years before appearing in that action-comedy take on the Middle Ages, Ledger starred in a modern-day teen comedy inspired by a play written in the 1590s by no less an eminence than William Shakespeare.

Ledger’s 10 Things I Hate About You Is A Streaming Hit On Prime Video

Ledger’s rare comedic turn in 1999’s 10 Things I Hate About You, a modern-day take on The Taming of the Shrew, has helped the movie become a streaming hit in 2025. It was a hit when it came out too, grossing $32.8 million domestically ($85 million adjusted for inflation) on a budget of $13 million.

Teen comedy had plenty of box office appeal back in 1999, and it’s still a strong genre in the streaming world, as 10 Things I Hate About You is a success all over again, landing at #9 on Prime Video’s current Top 10 chart.

Why You Should Watch 10 Things I Hate About You

The term “teen comedy” can be a turn-off to some, but 10 Things I Hate About You is not a typical example of the genre. Taking a cue from Clueless, which adapted Jane Austen’s Emma into a modern-day comedy with spectacular results, 10 Things successfully reworks a Shakespearean relationship farce into a 1990s-set high school rom-com.

A clever script helps elevate 10 Things above standard teen comedy fare. Ledger is charming as Patrick, while Julia Stiles shines as the anti-social Kat. Those who are into ‘90s fashion will be captivated by the film’s costumes, which were memorable enough to be written up by Vogue in a 2025 piece celebrating the movie as a ’90s time capsule.

10 Things I Hate About You also boasts a strong soundtrack, including a pair of tracks by Letters From Cleo, plus songs by classic ‘90s bands Semisonic, Save Ferris and The Cardigans. Though the film’s retro appeal is indeed very strong, it still holds up as an offbeat romantic comedy, thanks to its lead performances, and its amusing Shakespeare-derived story.