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Just to be clear, I am not starting with a rectangular text box and floating around an irregular image. I am creating an arbitrary shape then typing in text to best fit into this shape.
Is there a jquery plugin or in html5 canvas? Is this even possible yet?
If you’re able to provide boxes which describe the shape, you might be able to use CSS3 Regions. Availability in your target browsers might be pretty poor though. This is probably the spec Šime mentioned.
SVG also claims support for this in an SVG 1.2 working draft. I’m not clear whether this has made it to a W3 Recommendation, or whether it’s actually supported in browsers.
Update: the answers to this question suggest the SVG approach won’t work right now.