He's not that much of a pretty boy

I think they probably meant 'fresh faced' compared to most of the people he was expecting to see in there.. He's quite young, not particularly big or muscly and has no scars (he probably wanted scars to make himself look tougher). I personally think he should have used the time he had to make himself tougher.. I guess we don't know how long he had but he could have started going to the gym rather than clubbing to make him more able to defend himself

Well, I'd suggest you to watch some documentaries about prisons, check how guys look like in there. Of course Edward Norton is no Paul Newman; but he'll be an Angelina Jolie when it comes to a prison. That's why he wanted to have a *beep* up face and probably end up with scars so he will look like a dangerous type.

But he could also ask for some protection from his Russian mob connections too, instead of turning his back to them.

Also this film is adapted from a book. Monty in the book portrayed as someone who would be so mouch trouble in prison with how he looks, so they just stay loyal to the book's storyline.

I was thinking the same thing, Fefu!

Yeah, Ed Norton is not only handsome but incredibly talented.

I'd never notice him in public, myself.

But: Slender young white guy, no noticeable scars or tattoos on him, with nice teeth, skin, and hair? He's very pretty, for prison. Context is crucial here.

"I gave you a haircut, not a lobotomy!"

Or Montgomery Clift? Lol!

I think the pretty boy stuff was made in reference to the prison inmate population. He would be a pretty boy in there