As a former teenage outcast of the highest (lowest?) order, I'm particularly sensitive to the depiction of adolescent Ishmaels on film. And truth be told? A fair amount of Hollywood movies simply don't get it right.

It takes a lot of elements to render a convincing teen or pre-teen geek, goth, nerd and/or loner on film, from the acting to the writing to the directing to the wardrobe department -- and a few select movies have nailed it. "Carrie"? "Welcome to the Dollhouse"? "Ghost World"? All have realistically rendered the pain of adolescent pariah-dom on film. The films listed below, on the other hand? Not so much.

As "The Duff" hits theaters, let's take a look back at nine terribly unconvincing teenage outcasts in the movies.

See also: 10 Great High School Mean Girls on Film

A former contributor to sites including MTV's The Backlot and Bloody-Disgusting, Chris Eggertsen worked in film development before indulging his love of pop culture writing full time. He specializes in horror, the intersection of social issues and entertainment and Howard Stern. He's on Twitter @HitFixChris.