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Making a drawing a token/portrait/pog.

Just started up a campaign. The DM who introduced me to Roll20 took the images we selected for our characters and turned them into round portraits that he cropped from the images. I can't figure out how he managed to do it. All I've managed to do is size a drawing, potentially cropping it before uploading it, to the size appropriate, then make it a player-controlled token. It'll work, but it just doesn't look clean. Is there a tool to make a pog out of an image that I'm just not finding, or does it take a 3rd-party program. If the latter, any good suggestions?
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It's a 3rd party thing, mostly. TokenTool does that and there's another one that I can't remember off the top of my head, as far as stand-alone programs go. A number of people use graphics programs like Paint.net(me), GIMP or Photoshop to do the same thing.
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Thanks. Now to find a tool to automatically clear the player's graffiti from the background (without having to "Clear all Drawings" myself.) Then I again, I could just move the scrawlings over their tokens and say "How odd... part of the cavern roof collapsed on you in the form of recognizable English (Which, unfortunately, your character does not speak. They speak common .) You take 3d6 damage as you are crushed."