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What’s the best way to add vertical pictures to my video?

Place a copy of the vertical picture on a lower track right under the original in Vegas. Then crop it to fill the screen and add a gaussian blur. What now shows through on the sides of the vertical picture will be a blur of the original texture that the picture already has. This makes the fact that its vertical much less distracting than vertical black or colored bars. For an optimization, save the blurred event on the lower track as an image and delete the original event and add the image back. This will speed up rendering since VV won’t have to apply the blur to the whole event. It just renders the already blurred image.

Alternately you could do all this in photoshop to the vertical picture in advance. I’d imagine you could write a macro to copy the image, crop it to 655×480 (i.e., full width), blur it, and paste the original back into it. Either way, the results are much, much, nicer than black borders.

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