4. Trent
Behind the stoned slacker persona, Trent is actually a really intelligent guy, as evidenced by his ability to go back and forth in verbal exchange with Daria, Jane, and Tom. Let's be honest, even a mindless crush has standards, and Daria would never have one on an idiot. Trent has some of the best one-liners in the series. He's relateable enough, as we all knew people exactly like this. Pretty smart, just not motivated to do much with it.
http://www.outpost-daria.com/ch_trent.html
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SmartMuffin - Because anything less would be uncivilized - http://img.imgcake.com/smartmuffin/barkleyjpgde.jpg
http://dudewheresmyfreedom.com/