30: Be Kind, Rewind: The 90s–00s Movie Bracket

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Pop in your VHS, grab the popcorn, and let the millennial movie madness begin.

We created the ultimate 64-movie bracket to crown the most iconic film of the 90s/2000s — from Clueless to The Matrix, The Lion King to Wedding Crashers. Categories include Disney bangers, teen rom-coms, cringe comedies, and blockbuster hits.

We each filled out our brackets live on the pod — which means a lot of passionate opinions, unexpected upsets, and a few “wait… you picked that?!” moments.

Which movies reigned supreme?

Which got eliminated faster than a Tamagotchi left in your backpack over spring break?

This one’s nostalgic, slightly unhinged, and full of movies that raised us — whether they aged well or not.

Tune in, play along, and let us know where your bracket went off the rails.

Intro & Outro music gratefully provided by our wonderful pal Captain Luke. Cover photo by the radiant Noelle Johnson.

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