Remembering the most amazing teen movies from 1999

In 1999, the world was given three classic teen movies: She’s All That, Never Been Kissed, and 10 Things I Hate About You. These films all had a few very important things in common: the “quirky” female lead, the highly attractive love interest, and—most importantly—PROM.

In appreciation of how it has been 15 years since these movies came out, I have selected some of the best moments from each of them.

She’s All That

Released in January 1999 and based on George Bernard Shaw’s Pygmalion, She’s All That follows the relationship of introverted artist Laney Boggs (Rachael Leigh Cook) and high school stud Zachary Syler (Freddie Prinze Jr.). After a split from his girlfriend, Zac makes a bet with his friends that he can turn “ugly duckling” Laney into the senior prom queen in six weeks. Queue makeover scene (ALL THEY DO IS TAKE OFF HER GLASSES AND GIVE HER A HAIRCUT BUT WE LOVE IT). Also starring the late, great Paul Walker, plus Matthew Lillard, Anna Paquin, and a very adorable Kieran Culkin.

Top 3 Moments

Buffy’s in it.

When she walks down the stairs. . .

. . . And this happens.

That poolside kiss.

Never Been Kissed

Released in April 1999 and loosely based on Shakespeare’s As You Like It, Never Been Kissed follows Chicago Sun Times reporter Josie Gellar (Drew Barrymore) as she poses as a high school student to write an exposé on modern-day teens. However, as she lacks “rufus” qualities (if you’ve seen the movie, you’ll get this humorous wordplay), this proves difficult. The movie also stars Michael Vartan, Jessica Alba, David Arquette, John C. Reilly, Molly Shannon, and—you have to look really carefully for this one—James Franco.

Top 3 Moments

That outfit.

This line.


10 Things I Hate About You

Released in March 1999 and based on Shakespeare’s Taming of the Shrew, 10 Things I Hate About You follows sisters Kat and Bianca Stratford (Julia Stiles and Larissa Oleynik) and their dating escapades (or lack thereof). Their father, Dr. Walter Stratford (Larry Miller), will only allow Bianca to date when Kat does. Complications and hilarity ensues with the sweet Heath Ledger, a young Joseph Gordon-Levitt, and Gabrielle Union.

Top 3 Moments

The poem.

When Patrick serenades Kat (because SWOON).

And badass Bianca.

And now, I leave you with the musical talent of Sixpence None the Richer (featuring Rachael Leigh Cook and FPJ!).

Didi Kaur lives in London, born and raised. Loves Harry Potter, a good chick flick, the 90’s. . . and also, cookies. Nothing makes her happier than binging on television. And cookies.

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