Top 5 hilariously stupid characters of the 2000s

5. Madison – Zombieland: Double Tap

If the world ever fell to a cliched zombie apocalypse, you’d think the stereotypical dumb blondes would be the first to go. Luckily, this one got the bright idea to take refuge in a freezer. The downside is that she’s been by herself for years, cut off from anyone else to talk to (or tell her how stupid she is). As such, she’s quick to show her affections and blurt out any insipid observation that comes to her little mind.

For better or worse, Zoey Deutch perfectly embodies the stupid valley girl persona, her bubbly demeanor, and dainty gestures easily selling this airheaded character. This may sound odd, but it’s surprisingly refreshing to see someone who acts like this.

Someone this easily amused and who’s still concerned with first-world problems contrasts beautifully with this dangerous zombie world. It’s even more so considering how jaded the protagonists are at this point. I don’t think many people expected a character like this in the long-awaited sequel to Zombieland. I’d guess that fewer still expected her to be one of the best parts.

4. Joey Donner – 10 Things I Hate About You (2009 TV Series)

An underappreciated TV remake of the 1999 film, this show makes some notable changes to its source material. No, it doesn’t get any closer to Shakespeare. Instead, it shifts a few of its characters around, thereby altering the whole dynamic. One such player is Joey Donner, the malicious misogynist who served as the film’s villain.

Here, however, not only is he hopelessly stupid, but he’s basically a slave in everything but name. While he’d like nothing more than to pursue his dream of modeling, he’s forever at the beck and call of his domineering cheerleader girlfriend, Chastity.

This helps him to garner sympathy, but he’s never played as a tragic figure. Oftentimes, he’s the happiest one in the room. Whenever someone else is feeling down, he pulls out a seemingly unrelated metaphor to solve the problem and actually manages to make some sense out of it through his own juvenile logic.

When combined with Chris Zylka’s dopey smile and enthusiastic delivery, this makes it hard to hate him even when he’s technically in the way of the other characters. It’s a radical new direction for such a prominent character, but it pays off in spades.