41: “A Waste of Perfectly Good Yearbook Space” – 1999 Prom-Coms


We bet you can’t make that girl with glasses listen to this podcast. In our latest episode, we look back to the teen movie explosion of the late 90s via SHE’S ALL THAT, NEVER BEEN KISSED, and 10 THINGS I HATE ABOUT YOU, all released in the first few months of 1999, and all culminating at — where else? — the prom! (Gasp!)

If you don’t think Drew Barrymore, Rachael Leigh Cook, and Julia Stiles are three of the world’s least desirable women, you may have trouble buying the mischief and shenanigans teen boys resort to in search of true love. This was the moment in pop culture when teen entertainment took a cue from Shakespeare and other classic literature — without doing much to update centuries-old sexual politics. If you thought 80s teen comedies were problematic, wait ’til you get a load of the sexist, stalkerish antics of 90s dreamboats like Freddie Prinze Jr., Heath Ledger, Andrew Keegan, Paul Walker, and Joseph Gordon Levitt!

Are any of these 1999 prom-coms “all that,” or are there 10 things to hate about each? We hope you rented a limo to fit all the snark, angst, and inappropriate romance of these teen comedies!

When We Were Young is a podcast devoted to the most beloved pop culture of our formative years (roughly 1980-2000). Join us for a look back to the past with a critical eye on how these movies, songs, TV shows and more hold up now. You can follow us on Twitter and Instagram at @WWWYshow, on Facebook at Facebook.com/WWWYShow and you can email us your episode suggestions at wwwyshow@gmail.com. Don’t forget to subscribe and review us on iTunes!

Help us defray the costs of creating this show, which includes purchasing movies/shows/music to review, delivery food to eat our feelings, and producing & editing in-house at the MFP Studio in Los Angeles, California, by donating to our Patreon account at patreon.com/WhenWeWereYoung.

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