Take Two: The 2000s Comedy Movies That Raised Us

Back in Season 1, we recorded an entire episode about 2000s comedies…and then locked it away in the WYM vault.  So this is our official Take Two: the comedies that defined the 2000s.

From sneaking into R-rated showings at the Carmike to quoting Anchorman until it was tattooed on our brains, these movies were more than entertainment—they were cultural moments. Some only hit because we were teenagers, others were ahead of their time, and a few are still comfort rewatches today.

This week we’re putting 2000s comedy classics head-to-head: Will Ferrell vs Ben Stiller, frat boy weddings vs stoner smacks, Napoleon Dynamite vs Juno, and more. We’ll debate which ones hold up, which ones aged like milk, and why comedies don’t land in theaters the same way anymore.

Plus: Quote battles, soundtrack shoutouts, a round of Petty or Valid: Movie Edition, and the ultimate question—if you could only keep one 2000s comedy forever, which one makes the cut?