I noticed this last night while I watched I Love You, Man for the third time. When Sydney pays for those billboards for Peter Klaven, he uses the picture that he took of Peter while trying on suits for his wedding. This made the James Bond themed billboard right? Then there were the others like the Ali G rip off, the cowboy one, and the muscly body billboard which were obviously photoshop with random pictures Sydney had of Peter. Although, there was one billboard that is unexplained.
In this billboard it shows the infamous picture of Paul Rudd that is all over the internet, yet never explains why Sydney has this image, nor gives a moment when it was taken. Also, we already know this image is real and had been on the internet before the movie was made. So why use it?
I suppose John Hamburg felt he had perfectly good picture of Paul Rudd that he wasn't going to put to waste, and it worked, it was still funny as hell.
So jump on it