A bit late to the party, but hopefully I can still add a thing or so...
...it is difficult to watch Wrestling with Shadows without at least some sense that the whole thing was set up. It's incredible timing for the documentary filmmaker, and certainly a brilliant response from McMahon. The creation of the McMahon character seems largely to have made Steve Austin who he is.
Was it all set up in advance? Was Bret playing along? Well, my feeling is, if not, he probably should have. The "reasonable creative control" mentioned in one of Joshua's posts should have been a red flag as to the kind of business he was in. Not wanting to lose in Montreal because it's his hometown? Leaving aside that his hometown was technically in a different province, what reasonable person, having worked for McMahon, would expect to have much pull in an angle as carefully worked out as Bret v. Shawn. And that Vince would let him win the match, trusting that he would turn over the belt after (despite the problems that always seem to occur when a champion leaves)? There's a joke in High Fidelity about asking for a dollar, getting turned down and then asking same person for 50 grand, and it seems appropriate here. Bret was an employee, and should have expected something was up when McMahon agreed to negotiate with him in the slightest.
After all, as J.R. said, there's not always a lot of difference between Vince and Mr. McMahon.
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The emotions and problems afterward definitely indicates that this was not a set-up for those conspiracy theorists who thought so, which makes the whole situation feel all the more unreal when you watch the documentary. In the end, because WCW botched Bret's character so much and because of his concussion, WWE definitely got the most mileage out of Montreal, but the shame is that it should have shot Bret into superstardom from the start in WCW.
As we've learned ourselves, there really isn't that much difference between Vince and Mr. McMahon. Wrestling with Shadows really reinforces some of the thoughts viewers have had over the years of McMahon as a villain in and out of the WWE. If we put some of the details of the Bret Hart story that is presented aside, we see how throughout the film McMahon is built up to be the bad guy. It seems that the documentary itself serves this double purpose--presenting Bret Hart as the fallen hero and McMahon as the heel. McMahon does much of the same thing. Though the expressed intent is to inform and present, those who are interviewed throughout the documentaries and the footage that is shown puts a particular spin on the films' real purpose. We get the idea that there is more than meets the eye; indeed, the idea, that the whole thing is staged.
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