Robert "Bob" Paulson
Robert Paulson, called Bob, is a victim of testicular cancer who has grown breasts due to his hormone therapy. His wife and children have abandoned him, and he finds solace by attending a support group and by building a friendship with the Narrator, whom he knows as Cornelius. Bob later joins Fight Club and Project Mayhem and dies as a result of participating in a terrorist activity.
Bob is perhaps the most symbolic character in the movie. Marked by his breasts, he represents the Narrator's last grip on his caring, "feminine" side. He is the one that first convinces the Narrator to cry and thus show his "weakness," thereby attaining peace. He continues to be the Narrator's weak spot throughout the movie. The disintegration of the Narrator's femininity is symbolized when Bob joins Fight Club, but he continues to care about Bob, as shown when he breaks Tyler's rules by convincing Bob not to give up on being admitted into their "army." In short, the Narrator betrays his masculine side, portrayed by Tyler, for his feminine side, portrayed by Bob. Ironically, however, this action will cause Bob's death, showing that there is no room for softness or compassion in Tyler's vision of a testosterone-dominated future. Bob's death is the final event that convinces the Narrator that Project Mayhem has gone too far; it is the catalyst that sends him on his search for Tyler. Bob makes the Narrator realize that some sacrifices are just too much.
Freezon writes, "I would like to point out about Robert Paulson that he was the only member of Fight Club allowed to fight with his shirt on, a direct violation of the rule: "no shirt, no shoes". I can't glean any symbolism, perhaps someone else can. He was the only member with tits, however." My take on this is that either Bob was exempt from the no shirt rule because of his, um, chest and the Narrator simply didn't mention it, or it's a deliberate slip in the movie's logic, made to catch the viewer's attention.
Freezon has added more comments: "after watching the movie again a few more times i noticed that bob is allowed to break all of the rules at various times...he talks about fight club (w/ jack), the shirt, he leaves the porch during his 3 day trial period to enter project mayhem (jack talks him into staying), he is referred to by name by the narrator even though their names have been taken away in project mayhem, etc.... ..he may be allowed to break the rules because jack first found the beginnings of his new path crying between bob's bitch tits..."
Nick also has some thoughts on Bob's shirt. "First, and not of much importance, but, I also noticed in the movie that Bob was allowed to wear a shirt. I do not think it is related at all to symbolism. Rather, I think it is actually just part of the cinematography. Bob's character most likely wore a body suit to portray his large breasts, and if you have ever seen these body suits you will know that they are not flesh looking. I think they (the cinematographers) had Bob in a shirt to cover the body suit. Otherwise, Bob's costume would of had to been much more complected and costly."
Alan has the answer to the controversy: "I believe in the director's commentary they mention that they wanted a chest prosthetic for Bob to fight in, but it just didn't look right so they had him wear a shirt. It sounds like there was no intended symbolism. I don't remember what happened in the book." From what I (Togemon) can remember, the issue wasn't mentioned at all in the book.