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In the many Red Dead Redemption trailers, they use this cool effect were paint/brush strokes somewhat pan into the actual game-play and overlay it with an awesome drawn out piece from the previous frame - what I am trying to do, is recreate just that.

An example is :

at 0:11 and 0:17

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It's a lot of matte painting. While the video is still running, they animate a semi-transparent shape (probably made in Illustrator or something similar) and animate the shape in over it. As soon as the painting finishes, they switch to a frozen shot of the last frame and seem to transition to the painted version of that frame. It's hard to tell exactly from the Youtube video since I can't frame advance, but that should get the general feel of it.

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Down and dirty and did I say simple?

Alternately in Vegas Pro under the transitions tab is a group of transitions called gradient map. In this group is a paint stroke or splatter like transition. First set the fade time on the clip(s) then add this effect by drag and drop. You'll find it's more like a drippy paint than a stroke, perhaps you can fiddle with the settings of this transition to season to taste.

You could use this effect with a solid background color field and blend with your next scene, just another track to add, but be aware that you will may need to play with the compositing method to see what looks best: add, subtract, dodge, burn, difference, etc.

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Pause your live video on the frame that you want to animate.

Export that frame into something like photoshop or illustrator.

Design several "painted" layers over your still frame.

Export the layers back into After Effects.

Animate some masks to expand across each of the layers, to appear in such a way that they appear to be painted on.

To improve the effect, you could use some stock animated footage of brushed paint as a matte layer.

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