Guide Mentor

Character Role Analysis

Chuck Bolger

We're gonna pick Chuck because he's the most prominent, but there's a whole passel of Jack's hooligan friends who might fill this role. (Mom might also be a guide/mentor of sorts, but she's a bit too flaky.) Chuck encourages Jack's petty criminal tendencies, gets him to drink, and otherwise brings out the dark side in Jack:

He was haunted and wild, but his manner was gentle; even, at least with me, brotherly. For that reason, I felt easier with him than I did with the others. (20.12)

Even when their connection falters at the end, they can still pretend, and Jack really looks up top him like a brother. That's not exactly healthy, but hey, it beats Dwight any day of the week (and twice on Sundays).