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I need some way of making text (more specifically, the chorus for a song for a graphic arts project) be fitted to the outline of a silhouette.

The effect I wish to achieve is much like this piece of shape poetry:

example

Does anyone have recommendations on software (preferably for the Mac OS), web app or website that can generate this kind of thing?

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This actually looks like you might be able to do with something like inDesign or Illustrator - just create a text block, enter your text, and add / move points to the text box shape until you have your desired shape.

Or...

create your shape in Illustrator, click on the shape, and enter / paste your type.

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For lengthy prose copy (such as in an ad, or sidebar text shaped purely for effect in a layout), pasting into a shaped frame in Illustrator or InDesign is usual, as lawndartcatcher has indicated. In such a case the copy often must be edited to fit the space available, however. For a short song segment or poem it makes much more sense to simply choose appropriate line breaks to achieve the effect you're looking for. You don't need special software.

This type of poetic conceit traditionally uses straight typography and the writer's choice of line breaks. The desired shape also influences word choice in such a case. (The mouse's tale/tail in "Alice in Wonderland" is something of an exception, but that merely adds to the humor. Note, however, that it was originally set in metal type, without benefit of software.)

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